Here's the core issue. Decades of tax deferral during high earning years allow retirement accounts to grow substantially. Over time, those accounts often become the largest part of net worth. The problem is not the saving. The problem is what happens when required minimum distributions begin. These RMDs are not based on lifestyle needs. They are based on account size. The larger the balance, the larger the forced withdrawal. And those withdrawals are taxed as ordinary income. They stack on top of Social Security, pensions, deferred compensation, and sometimes part time work. That is how many clinicians end up in their highest tax years after they stop working.

The common assumption that taxes drop in retirement: it does not always hold true for prepared professionals. Retirement changes where income comes from, not necessarily how much income there is. Social Security taxation depends on total income. Medicare premiums increase when income crosses thresholds. Strong market growth can quietly increase future RMDs. Income can show up whether we want it or not.

The most valuable planning window often happens before RMDs and Social Security begin. Those transition years between retirement and age 73 can offer meaningful control. If income temporarily dips while net worth remains high, we may have opportunities to shift assets strategically.

What about Roth conversions? They are not about avoiding taxes. They are about choosing when to pay them. By moving money from traditional IRAs to Roth accounts during lower income years, we reduce future RMDs and create flexibility. Now, these conversions can feel uncomfortable because they increase short term taxable income and may affect Medicare premiums. But we emphasize that the real goal is to reduce sharp income spikes later.

Again, these tax issues are often the result of doing everything right. Flexibility matters more than perfect timing. Thoughtful planning today can prevent forced decisions later.

(00:00) Introduction
(00:51) How 403(b) and 457(b) Plans Create Future Tax Risk
(02:59) Why Taxes May Not Drop in Retirement
(04:36) Social Security and Medicare Income Traps
(07:01) The Transition Years Planning Window
(10:26) Understanding Roth Conversions
(14:46) How Early Planning Reduces RMD Pressure
(16:17) The Power of Tax Diversification
(18:21) Key Takeaways for Clinicians

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

We start by exploring how tech income is rarely just a paycheck. When restricted stock units (RSUs), employee stock purchase plans (ESPPs), bonuses, or job changes are layered on top of a base salary, tax situations become more complex. These types of income show up in chunks and are taxed differently, often creating withholding gaps and surprises at filing time. Most payroll systems handle base salary well, but they may fall short when irregular income is involved.

We walk through how RSUs are taxed at vesting, and how withholding often underestimates what’s truly owed, especially for higher earners. ESPPs add another wrinkle: taxes are triggered when shares are sold, not purchased, and withholding is often absent entirely. And bonuses, while taxed as regular income, are frequently withheld at flat rates that don’t match the recipient’s tax bracket. This leads to confusion and contributes to the myth that bonuses are taxed more heavily.

Throughout the conversation, we emphasize that withholding is NOT the same as actual tax owed, and that tax visibility (not perfection) is the real goal. We suggest starting the year by forecasting equity and bonus income, applying a rough tax rate, and comparing that to projected withholdings. If there's a gap, it's not a problem; it’s a signal to adjust.

We share real client examples, showing how a lack of planning around year-end RSU vests led to surprise tax bills. A few proactive steps, like setting aside cash when equity vests or bonuses hit, can prevent financial strain. We encourage creating a running file of key documents, such as vesting summaries, pay stubs, and equity sale confirmations, to simplify reporting and planning.

Finally, we outline a system for turning tax planning into a repeatable habit: review compensation annually, capture documents in real time, run a mid-year check, and coordinate with financial and tax professionals before tax returns are finalized. The message is clear. Calm comes from process, not hope. With the right approach, taxes can feel manageable, even boring. And in this case, boring is a very good thing.

(00:00) – Intro: Why Tax Season Feels Overwhelming

(01:40) – The Hidden Complexity of Tech Income

(03:00) – Where Tax Risk Typically Shows Up

(04:00) – How RSUs and ESPPs Are Taxed

(07:00) – The Bonus Tax Withholding Myth

(09:00) – Estimating Tax Exposure (Visibility > Precision)

(10:26) – A Real-World Tax Surprise Story

(12:32) – Gathering Tax Documents Throughout the Year

(14:45) – Managing Cash Flow from Equity & Bonuses

(17:43) – Building a Repeatable Tax Planning System

(19:17) – Final Thoughts: Calm Comes from Process

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

We start by addressing how fear-driven headlines can tempt people into making financial decisions based on emotion. Amy reminds us that headlines are built to provoke urgency, not provide clarity. Market fear is often noise, not rooted in personal financial change. Reacting impulsively often locks in losses and increases risk. That’s why we advocate for responsible inaction, a deliberate choice to stay the course unless personal circumstances demand a change.

A strong financial plan assumes uncertainty. It’s not built for calm seas, but for the real-world storms. That means including flexibility for job changes, a sufficient cash buffer, and the ability to adapt without starting over. Confidence grows from knowing your plan already factors in the unpredictable. It’s not about guessing what’s next. It’s about trusting the structure you’ve created.

We dig into the concept of guardrails. These are rules and pre-decisions made in calmer moments to help reduce decision fatigue. Healthcare professionals already follow protocols in their daily work, and the same concept applies to finances. These protocols guide us through emotionally charged situations and help prevent impulsive, regrettable moves.

Cash plays a unique role in confidence. For healthcare professionals, cash isn’t just an emergency buffer; it’s emotional relief. It offers flexibility, covers transition periods, and acts as a cushion during market downturns. However, it’s also important to avoid extremes. Too little cash creates anxiety, while too much slows growth. The right amount depends on career phase, income variability, and life responsibilities.

We close with the reminder that certainty isn't the goal. Resilience is. When a plan is built to withstand real life, it allows money to support your lifestyle, not compete for your attention. That’s where true confidence comes from.

(00:00) - Intro: Confidence Under Uncertainty
(00:47) - Why Healthcare Professionals Are Feeling Financial Strain
(01:25) - The Emotional Impact of Headlines
(02:12) - Market Fear vs. Personal Risk
(03:08) - What “Doing Nothing” Really Means
(04:51) - Is Your Financial Plan Built for Real Life?
(06:04) - Guardrails and Reducing Decision Fatigue
(07:30) - The Role of Cash in Building Confidence
(10:48) - Cash as a Confidence Tool, Not a Cop-Out
(11:00) - Final Thoughts: Confidence Comes from Structure
(11:33) - How to Connect with Thimbleberry Financial

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

We explore how burnout rewires our ability to make decisions. Stress from long hours and mental overload shrinks our decision-making capacity. This leads to automatic, often reflexive spending as a way to cope—ordering food, shopping online, or subscribing to convenience services not out of indulgence, but survival. Many of us say we make good money, yet still feel stretched. Amy explains this disconnect through the lens of decision fatigue and lifestyle inflation as coping tools, rather than conscious choices.

Then, we walk through Amy’s Burnout Blueprint, a three-pillar framework for using financial planning to support mental and emotional wellbeing. The first pillar is intentional spending. We learn to distinguish between energy-saving expenses, like cleaning services or meal prep, and stress-coping spending that signals a deeper need for rest or support. We hear how small shifts—like outsourcing chores—can buy back time and change our relationship with money.

The second pillar is career pacing. Amy shows how financial clarity gives us room to pause, reassess, or even take sabbaticals. Instead of being chained to the next RSU payout or promotion, we can model what “enough” looks like and make career decisions from a place of health, not fear.

The third pillar is structured downtime. Real rest requires more than intention—it requires the freedom to disconnect without guilt or financial worry. Whether it’s a full sabbatical or just a microbreak, planning for rest helps rebuild energy and perspective. We also look at underutilized workplace benefits that can support recovery and reduce costs.

To wrap up, Amy leaves us with a powerful reminder: burnout isn’t a personal failure—it’s a mismatch between demands and energy. Small, intentional changes around spending, work, and rest can restore control and support our overall wellbeing.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

We start by recognizing how identity plays a major role. Many in healthcare see themselves as protectors and planners. Saving becomes a symbol of safety, and shifting to spending can feel like breaking an internal rule. With the end of scheduled shifts and steady paychecks, many experience a sense of floating—losing the rhythm they’ve followed for decades. We clarify that this unease is normal, not a sign of poor planning, but a psychological adjustment.

We emphasize that the solution lies in structure. By creating an income plan that mimics the regularity of a paycheck, we restore the stability many retirees need. We walk through how to assemble an “income playbook”—a way to integrate pensions, IRAs, 403(b)s, HSAs, and savings into a cohesive plan. Each account gets a role, whether it’s for essentials or discretionary goals, and cash buffers protect against market swings. Automation is key here—turning on scheduled withdrawals and tax withholding brings back the rhythm retirees are used to.

We also break down the concept of retirement into phases: go-go, slow-go, and no-go years. Spending shifts naturally, so we help clients build flexibility into their plans. Travel and hobbies may define the early years, while later stages often involve more home time or increased healthcare costs. By projecting different scenarios and using guardrails, we help people make confident adjustments as life evolves.

Throughout, we stress that it’s okay to spend what you’ve saved. Retirement isn’t about hoarding your wealth—it’s about enjoying the life you worked hard to build. We suggest starting with a snapshot of your financial picture, visualizing what your days might look like, and even running a test month on future income to see how it feels. Ultimately, retirement is about shifting into a new, well-supported identity—one that still reflects who you are but in a new chapter of life.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

We open by anchoring the episode in Thimbleberry’s core values, especially simplicity. Amy stresses how the best financial plans aren't flashy—they're clear, flexible, and focused on what truly matters. We dive into the first cluster of lessons about money and planning, starting with the idea that clarity beats complexity every time. Fancy strategies may look appealing, but real success comes from plans that are understandable and actionable. A flexible plan, one that can adapt to life’s inevitable changes, always outperforms a rigid one.

We continue by looking at how emotions play into financial decision-making. Amy explains that emotions aren't distractions—they’re data. Recognizing fear, guilt, or excitement can lead to more empathetic and accurate planning. We don't need to know everything to make progress; staying curious and asking the right questions is often enough. That curiosity can help us avoid the traps of both overconfidence and paralysis.

As we shift toward life-focused lessons, Amy reminds us that success looks different for everyone—and that’s the point. Whether it's retiring early or spending more time with family, the plan has to fit the person. Life moves faster than spreadsheets, and that’s why regular check-ins and flexibility are essential.

Amy emphasizes that the best financial plans make room for joy. Planning isn’t about restriction—it’s about creating space for what we love, whether that’s rest, giving, or travel. Simplicity, while hard, is always worth it. And finally, a good plan isn’t static—it grows with us. It's not about being perfect; it's about evolving alongside life’s changes and building confidence as we go.

As we wrap up, we focus on three key takeaways for the new year: clarity, consistency, and curiosity. It’s not about predicting the future—it's about being prepared for it. And that preparation, rooted in simple, flexible planning, is what makes long-term success possible.

00:00 – Intro & Episode 150 Milestone

00:23 – 10 Years of Thimbleberry Financial

01:08 – Simplicity as a Core Value

02:15 – Lesson 1: Clarity Beats Complexity

03:23 – Lesson 2: Flexibility Over Perfection

03:49 – Lesson 3: Markets Don’t Care—Your Plan Should

04:33 – Lesson 4: Emotions Are Data

06:39 – Lesson 5: Stay Curious

07:22 – Lesson 6: Success Looks Different for Everyone

08:15 – Lesson 7: Life Moves Faster Than Spreadsheets

09:01 – Lesson 8: Make Room for Joy

09:31 – Lesson 9: Simple Isn’t Easy

09:57 – Lesson 10: A Plan That Grows With You

10:41 – Final Takeaways for the New Year

11:53 – Contact Info & Closing

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

We begin by examining the startup world—fast-paced, creative, and filled with uncertainty. It’s a space for people who love to experiment and thrive in ambiguity. The upside can be big: ownership, impact, and equity at low initial prices. But the downsides—unpredictable income, fewer benefits, and emotional strain—are just as real. Amy shares stories of clients who initially thrived in startup life but found it incompatible with long-term needs like family time or structured days.

Next, we shift to pre-IPO companies, which often represent a middle ground. These firms offer more stability than startups but still retain a sense of mission and momentum. Equity typically comes in the form of RSUs, and while there’s real potential for financial gain, it hinges heavily on IPO timing—something employees can’t always control. Amy emphasizes the importance of planning for delays, setting aside cash, and staying flexible when managing that equity.

Public companies offer clarity and predictability—stable salaries, strong benefits, and slower but more structured growth paths. For professionals seeking balance, or with greater family or financial obligations, this environment often provides the support and stability they need. The culture tends to be more formal, but that predictability can actually empower people to do their best work.

Ultimately, the conversation centers around fit—not which company is best, but which is best for us, right now. Personality, financial goals, and life stage all play a role. A startup might make sense early in a career, while a more structured setting could become the right choice later on. Amy reminds us that romanticizing a company type—or even our own preferences—can lead us astray, and encourages getting honest feedback from those who know us best.

We wrap by reinforcing that job decisions should balance financial and emotional fit. Before accepting an offer, it’s critical to understand the equity structure, total compensation, pace of work, and company culture. Especially in today’s tight job market, doing our due diligence can prevent long-term regret and position us to thrive both professionally and personally.

00:00 - Intro and Episode Setup  

00:49 - Startup Culture: Opportunity vs. Chaos  

03:19 - Pre-IPO Companies: Growth with Guardrails  

06:08 - Public Companies: Structure and Stability  

09:27 - It's About Fit: Personality and Life Stage  

11:43 - Culture, Pace, and Real-Life Trade-offs  

13:43 - When the Job Market is Tight  

14:17 - Takeaways: Equity, Compensation, and Culture  

16:44 - How to Connect with Thimbleberry Financial  

16:57 - Disclaimer and Wrap-Up  

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

We explore how this dual role adds emotional and financial weight. Many healthcare professionals become the “go-to” child in the family, shouldering time off work, travel, coordination, and often direct financial support. But as Amy reminds us, we can’t pour from an empty cup. Our ability to help others long-term depends on preserving our own financial health first.

We talk through the major financial decisions that come up—care settings for aging parents, sibling coordination, insurance gaps, and legal documents. There’s often an assumption that Medicare will cover long-term care, but it doesn’t, which leads to unexpected financial strain. Amy also highlights the importance of separating finances, documenting contributions, and maintaining clear records to protect relationships and ensure fairness.

A major theme we come back to is boundaries. Just like in an emergency on an airplane, we must put on our own oxygen mask first. For financial health, that means building a plan for ourselves before helping our parents. That clarity allows us to make better decisions, communicate expectations with siblings, and avoid jeopardizing our own retirement.

We also recognize the strengths healthcare professionals already bring—assessment, planning, communication, and monitoring. These are the same skills needed to manage a family’s financial and care responsibilities. Amy urges listeners to apply their professional mindset to this personal challenge.

Finally, we lay out five concrete next steps: gain financial clarity for both generations, start those tough conversations early, prioritize your own retirement, coordinate insurance and estate planning, and build a team of advisors, including financial planners and elder law attorneys. Sustainable care means both generations are supported—and planning ahead is the only way to get there.

00:00 - Intro
00:14 - The Sandwich Generation in Healthcare
00:49 - Emotional and Financial Weight of Caregiving
02:24 - Financial Decisions When Parents Need Support
04:59 - Sibling Dynamics and Hidden Costs
05:48 - Helping Without Sacrificing Your Retirement
08:33 - Applying Professional Skills to Family Finances
10:42 - Five Concrete Next Steps
12:21 - Sustainable Care Across Generations
12:42 - How to Contact Thimbleberry Financial

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

We also talk about how older stats around side hustles — like claims that 50% of people have them — still influence how we think today, despite more accurate 2025 data showing only 25% of adults actually have one. And affluence is often funded by invisible resources like family wealth or debt, which makes comparisons misleading and self-defeating.

Psychologically, we’re wired for social comparison, but our brains focus upward. We look at those doing better, rarely at those with less. That creates ever-shifting benchmarks for “enough,” raising the bar as others share their wins. On top of that, algorithms feed us more of what we engage with — usually success stories — which can skew our sense of what’s normal.

Amy walks us through the reality: the national savings rate is low (4–5%), emergency funds are thin (1 in 5 adults can’t handle a $100 surprise), and credit card debt is at an all-time high in 2025. Even those who look like they have it all together might be stretched thin.

Why does this all sting so much? Because we’ve tied our identity to our finances. Falling behind feels like failure. It hits at our self-worth and creates a stress loop: we feel behind, we spend to catch up, and that spending adds more stress. It’s emotional and financial burnout.

So how do we break the cycle? First, redefine goals based on our own needs. Track progress against your own goals — like building savings or reducing debt — not against someone else’s vacation photos. Curate your feeds to remove content that sparks comparison. Write down what “enough” looks like for you in terms of comfort, flexibility, and fun. Celebrate quiet wins like financial stability, and be cautious of lifestyle creep when your income rises.

Lastly, Amy reminds us to stay curious instead of competitive. Learn from others without turning it into a race. Real wealth and well-being come from clarity, control, and peace of mind — not what someone else posts online.

00:00 – Intro
00:35 – Why social media skews our perception
01:30 – Debt and side hustle myths
03:00 – Why we compare ourselves psychologically
04:50 – The illusion of success online
05:50 – What’s really going on financially nationwide
06:50 – Why it hurts to feel behind
07:40 – The emotional and financial cost of comparison
08:45 – How to reset your goals
09:40 – Avoiding lifestyle creep
10:25 – Final takeaways and closing

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

We walk through vesting schedules, with one-year cliffs and subsequent payouts over several years being the norm. The concept of “golden handcuffs” comes into play, where employees lose unvested RSUs if they leave a company, adding a layer of retention-driven strategy from employers. We also dig into the tax implications, emphasizing that there’s no tax when RSUs are granted—but they are taxed as ordinary income once they vest. Many people mistakenly assume the company’s withholding covers the full tax liability, but that’s often not the case, especially for high earners.

The conversation gets technical but clear, explaining how the timing of selling RSUs affects how gains are taxed—short-term gains being taxed as ordinary income and long-term gains benefitting from lower capital gains rates. We debunk the myth of “double taxation” with a simple timeline that separates the grant date, vesting date, and eventual sale date, highlighting how only the gain beyond vesting is taxed again.

We then explore the decision of whether to hold or sell RSUs. It depends on individual circumstances, but key factors include overall exposure to the company through salary, stock, and other equity compensation. Concentration risk becomes a big deal, especially if both partners in a household have RSUs at the same company.

Common mistakes include underestimating tax obligations, overconcentration in employer stock, and failing to plan for tax bracket changes due to RSU income. On the opportunity side, we point to strategic uses of appreciated RSUs—such as charitable donations and goal-based selling. With RSUs becoming more common outside of tech and market volatility remaining high, understanding your vesting schedule and strategy has never been more important.

We wrap up by encouraging listeners to treat RSUs as part of a broader financial plan, not just as a bonus or windfall. Intentionality is key, and professional planning can help manage risk and make the most of these powerful compensation tools.

00:00 – Intro & RSU Basics
01:23 – What Are RSUs and Why Do Companies Offer Them?
02:43 – Vesting Schedules Explained
04:11 – Tax Implications at Vesting
07:29 – Capital Gains on RSUs
09:10 – Myth Busting: Are RSUs Double-Taxed?
10:00 – Should You Hold or Sell RSUs?
11:12 – Risk Exposure and Concentration
13:20 – Common Mistakes with RSUs
14:06 – RSU Opportunities and Strategic Planning
14:52 – Why RSUs Matter in 2025
15:39 – Final Takeaways on RSU Strategy
16:31 – How to Contact Thimbleberry Financial

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

We start by clarifying what T-bills actually are—short-term loans to the U.S. government, ranging from four weeks to a year. You buy them at a discount, and the difference between the purchase price and the face value at maturity is the interest you earn. While social media often touts them as risk-free, we explore why that’s only partially true. T-bills carry almost no credit risk, but they do carry inflation risk—if inflation outpaces your return, you're effectively losing money.

Next, we tackle the common claim that T-bills always outperform savings accounts and CDs. In some market conditions, that’s accurate—especially since T-bills are exempt from state and local taxes—but not always. High-yield savings accounts or promotional CDs can sometimes be more competitive. The idea of “guaranteed returns” is also addressed; while T-bills pay a set amount, they don’t roll over automatically, which means you need to be actively involved to maintain any momentum.

We also discuss the often-referenced Warren Buffett angle. Yes, Buffett uses T-bills—but only as a parking lot for cash while waiting on bigger investment opportunities. He doesn’t treat them as a core piece of his long-term strategy, and neither should the average investor without considering context and goals.

When it comes to retirement planning, T-bills can be part of the equation—but they aren’t universally ideal. They work for retirees focused on capital preservation, but younger investors risk missing out on growth if they lean too heavily on T-bills. We emphasize that T-bills are a tool, not a one-size-fits-all solution.  Again, diversification of investments is key.

The takeaway is clear: T-bills can serve a purpose—whether as a component of a cash reserve or a conservative bond alternative—but only when used with intention and in alignment with a broader financial strategy. Social media often oversimplifies investments for the sake of attention. We encourage listeners to approach these decisions thoughtfully and critically.

00:00 – Introduction & T-Bill Hype on Social Media
00:47 – What Are T-Bills, Really?
01:46 – Are T-Bills Risk-Free?
03:00 – T-Bills vs. Savings Accounts and CDs
03:53 – “Guaranteed Returns” – Fact or Fiction?
05:08 – The Warren Buffett Argument
06:00 – Are T-Bills Good for Retirement?
07:13 – Using T-Bills Strategically
08:43 – The Real Lesson on Financial Tools
09:25 – How to Connect with Thimbleberry Financial

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

We begin by stressing the importance of having a vivid goal. It’s not enough to have a vague intention—our goals need to be visualized, named, printed, and emotionally connected to. Once the goal is in place, we choose a structure that fits our personal motivation style. For some, it's a streak counter; for others, it’s hitting milestones, unlocking levels, or incorporating random rewards. The key is to tailor the game mechanics to what actually drives us.

Next, we build structure around the game by defining clear rules—written rules—to eliminate ambiguity and reduce the temptation to bend the system. Amy emphasizes the importance of including predefined exceptions so we can respond to life’s inevitable hiccups without feeling like we’ve failed. Automation plays a huge role in eliminating friction; it ensures that we follow through without having to rely on willpower.

We also talk about the power of accountability. Whether it’s a partner or a regular financial check-in, accountability helps us track wins, adjust strategies, and stay committed. And because humans respond to incentives, it’s critical to build a reward ladder. These rewards should be meaningful but proportionate—ideally no more than 10% of what we’re trying to save. We also look at the value of experience-based rewards, which generate longer-lasting satisfaction than material purchases.

To ground the theory, Amy shares a story about “Alex,” who gamified her weekday lunch spending. By creating a simple challenge, defining her rules, and building in smart rewards and penalties—including donating to a “liked but not loved” charity—Alex turned a small change into a sustainable habit.

When setbacks happen, we encourage listeners not to see them as failures. Reset the streak, learn from the moment, and evaluate whether the original goal was realistic. Symbolic penalties and honest reflection can help restore momentum.

We wrap up with a lightning round, debunking the idea that gamification is childish or time-consuming. It’s backed by behavioral science and can be managed with minimal effort through automation. Finally, we suggest starting small, being flexible, and aiming for traction—not perfection.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

We clarify that knowing you should save doesn’t automatically lead to action. That’s where gamification steps in. Tools like Qapital show that users who engage with automation and gaming strategies save more and stay more engaged. We also reference employer-based incentives like those offered through Secure 2.0, where bonuses are tied to increased retirement contributions.

One easy place to start is by automating just one transfer—no matter how small—to reduce decision fatigue. Then, to make it stick, we frame savings as something familiar and motivating. For example, we explore the idea of treating savings like a “debt to your future self,” flipping a psychologically powerful habit like debt aversion into a positive financial behavior.

Amy shares a client case study of a high-earning couple who couldn’t get traction with savings—until they started treating their savings goal like a debt that needed to be paid off. That mindset shift helped them redirect thousands per month into future-focused goals.

Then we move into more playful territory, introducing practical games to get people started. These include “Level Up” savings, where every $500 or $1,000 milestone brings a sense of progress; “No Spend” challenges, focused on key problem areas like Amazon or takeout; and visual trackers like progress bars stuck on the fridge. Even simple things like rounding up purchases and transferring the change can reinforce good habits.

The big takeaway is to pick one area where spending tends to leak—Amazon, dining out, etc.—and pair it with one of these gamified saving techniques. You can even stack methods for greater impact. The key is to make saving easier, more visual, and more rewarding—so it becomes a behavior you actually want to continue.

In part two, we’ll dive deeper into building out a full gamified system with recovery plans, rewards, and design tips. For now, we encourage listeners to find just one game that resonates and start today.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

We walk through how the strategy works: First, an individual makes a non-deductible contribution to a traditional IRA. Then, they convert those funds to a Roth IRA. The key here is that the contribution was already taxed, so the conversion should be non-taxable. The mistake happens when this sequence isn’t reported properly. We discuss how custodians like brokerage firms don’t know your tax strategy or income limits and cannot flag these issues for the IRS. So, if you're not proactively involved, you risk the IRS treating the conversion as fully taxable.

We unpack the three IRS forms involved: Form 1099-R (reports the conversion but not the tax status), Form 5498 (shows the IRA contribution but often arrives too late to help with timely tax filing), and most importantly, Form 8606 (tells the IRS the contribution was non-deductible and prevents double taxation). We emphasize that most errors occur because Form 8606 is either filed incorrectly or not filed at all. Without it, the IRS assumes your entire IRA is pre-tax, meaning future withdrawals will be fully taxed—even if you already paid taxes on that money.

Using a real-world example, we show how someone like “Jill” can end up paying taxes and penalties she didn’t owe, all because her CPA didn’t receive the full picture. This reinforces the importance of owning the communication and documentation process. We stress the need for record-keeping, proactively communicating with your CPA, and double-checking your return to ensure Form 8606 is present and correct.

In closing, we make it clear: the IRS isn’t malicious here—they can only go by what's filed. It's up to each of us to ensure our tax reporting matches our financial strategy. If you're going to use the backdoor Roth, you need to take responsibility for the reporting piece or work with an advisor who helps manage that process effectively.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

We start by defining what estimated taxes are: quarterly payments made directly to the IRS when withholding isn’t enough to cover total tax liability. This often applies to small business owners, but also to high-income W-2 employees who receive RSUs, ESPP income, large bonuses, or mid-year raises. Amy shares real-life examples of clients whose withholding fell short, either because RSUs were taxed at a flat 22% while their actual bracket was higher, or because payroll systems didn’t account for mid-year raises, leading to unexpected tax bills and underpayment penalties.

We then explore the IRS’s pay-as-you-go approach. If you've underpaid during the year—even if you pay in full by April—you could still face penalties. Jag and Amy emphasize how the system annualizes income, so a raise in July can retroactively affect your tax liability starting in January. This is where estimated taxes kick in, sometimes unexpectedly after filing the previous year’s return.

To determine whether you're subject to these payments, we explain the IRS safe harbor rule: if you pay 90% of your current year’s liability or 110% of the prior year’s, you generally avoid penalties. We walk through the process of calculating your total tax liability, subtracting what’s already been withheld, and deciding how to handle any shortfall—either through increased paycheck withholding or quarterly payments to the IRS and state.

Amy reminds us that overpaying gives the IRS an interest-free loan, so it's often best to aim for accuracy. Tools like financial planning software and coordination with a CPA can make this process manageable. The key is to review and adjust quarterly so you’re not blindsided come tax time.

We close with key takeaways: estimated taxes aren’t just for freelancers, income changes—whether yours or a spouse’s—can affect your liability, and proactive planning with a financial advisor and CPA helps avoid surprises. Most importantly, working with both professionals ensures smoother execution and better results.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

From there, we explore how conflicting or vague instructions can derail even well-meaning plans. When wills, trusts, and beneficiary designations don’t align, chaos can follow. “Fairly” and “equally” may seem interchangeable, but they’re not, and those subtle differences can lead to confusion, resentment, or even legal battles. We also caution against naming just one child with the “plan” that they’ll distribute assets informally—that’s a recipe for tax issues and strained family dynamics.

Ignoring taxes is another frequent oversight. Many people don’t realize how estate planning decisions can trigger income, capital gains, or estate taxes. Planning won’t erase taxes, but it can eliminate nasty surprises. We revisit digital assets too—crypto, photo storage, password managers—emphasizing that if no one can access them, they may as well not exist. These assets require thoughtful handling, not just from a distribution standpoint, but also accessibility.

Finally, we tackle the often-overlooked issue of naming the wrong fiduciary. This isn’t an honorary role—it’s a job. Too often people pick fiduciaries based on birth order, guilt, or assumptions rather than capability and willingness. We share stories illustrating how the wrong choice can create unnecessary complications, and how the right person isn’t always the obvious one.  Jag shares how he's not at all upset that his brother is in charge of their parents' estate.

To wrap, we recap all ten estate planning pitfalls discussed across both episodes and remind listeners to align legal documents, assets, and intent—while working with professionals who know how to navigate the complexity.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

The first pitfall we tackle is not having a will at all. If someone dies without a will, their state—not their estate—decides who inherits what, based on legal formulas that ignore personal relationships or intentions. These formulas differ by state and often don’t align with what people assume will happen.

Next, we highlight the danger of outdated documents. Many people who think they’re covered by old wills or plans don’t realize that state laws or life changes—like moves, marriages, or children—can render those documents ineffective. We share a story of a family who thought they were protected, only to find out their paperwork didn’t align with their current state’s laws.

Then, we move into beneficiary designations, which can override a will because they’re treated as contracts. If those designations are outdated, such as naming an ex-spouse, the wrong person could end up with assets, regardless of what the will says. This is why reviewing beneficiaries regularly is crucial.

The fourth pitfall is unfunded trusts. Setting up a trust isn’t enough—it has to be funded, meaning the assets need to be formally moved into the trust. Without doing this, the trust is an empty safe, and the probate process still applies. We discuss a case where a well-intentioned trust ended up being completely ineffective because it wasn’t properly funded.

Finally, we address the lack of incapacity planning. Many people forget to prepare for a scenario where they’re alive but unable to make decisions. Without healthcare directives or powers of attorney, families may have to go to court just to pay bills or make medical decisions—adding legal stress to already emotional situations.

We wrap up by reiterating the importance of having clear, updated, and legally valid documents in place—not just for your sake, but for those you care about. In Part 2, we’ll continue with the next five pitfalls to avoid.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

We start by emphasizing that prevention is key. Just like in medicine, the best remedy for burnout is early action, and that begins with building a solid financial foundation. We explore how consistent savings habits—even when it feels unnecessary—can offer crucial flexibility down the line. Setting aside 20% or more of each paycheck, creating an emergency fund with 6–12 months of expenses, and maintaining liquidity outside of retirement accounts are all smart, actionable steps. We also stress the importance of not delaying financial planning because you assume higher income gives you more time to catch up later. That’s a trap we see too often.

Next, we look at how to create income flexibility if burnout leads to reduced hours, a role change, or even early retirement. We talk through the importance of evaluating disability insurance—especially with mental health in mind—and how thinking ahead about possible career pivots like consulting or teaching can reduce stress. We also dive into the importance of building passive income streams and using investment strategy to bridge income gaps without needing active work.

For those considering early retirement, we advise updating retirement plans immediately to identify any needed changes, recalibrating spending, and optimizing the timing of account withdrawals to minimize taxes. We also cover how to smartly use pensions and healthcare benefits, especially when considering stepping away. Timing really matters here, and small adjustments can have outsized financial impacts.

Finally, we go over tactics to manage financial obligations during a career break—reducing debt, refinancing, and communicating with lenders. We talk about using COBRA, marketplace insurance, and HSAs to maintain healthcare coverage. The bottom line is that being proactive with money gives healthcare professionals the power to make the best choices for their well-being—financially and mentally—before burnout forces their hand.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

We walk through how to determine readiness for either scenario. For retirement, it’s essential to assess total wealth, stress test sustainable spending, and build a reliable paycheck from assets. For switching jobs, we need ample cash reserves and liquidity, as job searches are unpredictable in length. Equity compensation plays a central role—particularly what we leave behind. We highlight the importance of reviewing company plan documents to understand if retirement will trigger accelerated vesting or forfeiture of RSUs.

When it comes to timing, especially for those with stock options or RSUs, planning ahead is critical. If possible, we want to spread taxable events over multiple years to manage the tax burden more efficiently. We also discuss evaluating whether to hold or sell company stock after departure. The decision hinges on one’s financial goals, income flexibility, and risk tolerance. Behavioral aspects come into play too—avoiding regret by making informed, goal-aligned choices and not falling into the “shoulda, coulda, woulda” trap.

Taxes are unavoidable, but they can be managed with proper planning, especially when dealing with capital gains, ordinary income, and potential AMT from equity compensation. We stress the importance of integrating equity compensation into a long-term financial plan, using it to meet both short-term liquidity needs and long-term diversification goals.

Company-specific events like IPOs, mergers, layoffs, or vesting schedules can all influence the decision to leave. Evaluating those triggers through the lens of your goals helps in deciding whether to act now or wait. Lastly, we return to the value of working with a financial planner and the need for intentionality. Walking away—whether to retire or transition—is rarely simple, and it's okay to find the decision hard.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

We open by acknowledging that in many relationships, one person traditionally handles the finances. If that person passes first, the surviving partner can be left not only grieving, but scrambling to understand the financial puzzle. Amy shares how often she hears from women who feel anxious and uncertain when they’re suddenly in charge. These women aren’t incapable—they just haven’t been part of the process.

The heart of our conversation is about empowering both partners to be part of financial planning. Amy outlines the three big areas where questions tend to show up: understanding the financial picture, handling the emotional baggage around trust and confidence, and building knowledge to make informed decisions. It’s not about control—it’s about shared responsibility and kindness. We highlight how reframing conversations away from aging and death toward security and love can help bring both partners to the table more comfortably.

We also touch on how crucial it is for the financially involved partner—often men in older generations—to help build a bridge of understanding and trust. Amy uses the metaphor of setting up a tent: it takes both people holding up their corner to make the structure stand. We talk practical next steps, including setting up regular financial check-ins, building a “what-if” folder with key documents and passwords, and ensuring both partners feel respected and heard in these discussions.

Ultimately, we conclude that it’s never too late to get involved, and one of the most powerful legacies anyone can leave behind is a partner who feels confident to navigate life after loss. This isn’t just about money—it’s about care, connection, and preparing for a future that’s secure for both people in the relationship.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

We then explore how life events, especially the big and unexpected ones, impact planning. Medical diagnoses, large expenses, home changes, or receiving an inheritance—all of these can affect a financial strategy. We emphasize the importance of timely communication: the sooner we know, the better we can adjust the plan. Amy also reminds us that “big” is subjective. Our financial mindset and values shape how we define major changes, and that’s part of the data that matters, too.

Speaking of data, we clarify that every document request serves a purpose. Whether it's retirement summaries or tax returns, we ask only for what might improve the accuracy and depth of our advice. Sometimes, those pieces of information reveal benefits or pitfalls that clients weren’t even aware of, significantly shifting their trajectory. Taxes, in particular, often catch people off guard, and without returns in hand, it’s tough to diagnose the real issue.

As we dig deeper, we confront ambition versus reality. When clients want to retire early but aren’t on track for a more standard goal, we stress the importance of honest evaluation. If you're not ready to make the changes needed to hit the baseline, it's not useful to explore stretch goals. It’s not about being harsh—it’s about using everyone’s time wisely and avoiding decision fatigue.

We close by highlighting what a successful client-advisor relationship looks like. Clear communication, timely data, and realism about trade-offs are essential. When clients are engaged, responsive, and honest about what's possible, we can offer not just sound advice, but advice that truly improves lives. Financial planning works best when both advisor and client show up ready to collaborate with transparency and intention.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

We start with the immediate steps that need to be taken. First, a legal pronouncement of death is required, which is usually handled by hospital or hospice staff, but in cases of a home passing, 911 or hospice must be called. Then, notifying immediate family and close friends becomes a priority. This can be overwhelming, so enlisting help to spread the word is essential. Arranging transportation of the body, securing the deceased’s home and belongings, and taking care of any pets are also critical early tasks.

Next, we move into handling financial and legal matters. Obtaining multiple copies of the death certificate is key, as most financial institutions require them. Locating the will or estate documents helps determine whether probate is necessary. If the deceased’s assets were solely in their name, probate is likely required. However, if assets were jointly owned or placed in a trust, probate may be avoided. It's important to notify key institutions—banks, investment custodians, mortgage lenders, pension providers, Social Security, and credit card companies—to avoid complications like continued payments that may need to be repaid.

Probate can be a time-consuming and public legal process, so we discuss three common scenarios:

1. If assets are solely owned, probate is required to legally transfer them.
2. If assets are jointly owned, probate is not needed, and the co-owner retains full ownership.
3. If a trust is in place, assets can be distributed per the trust’s instructions without probate, saving time and legal fees.

After probate (or if it’s not required), the final steps include distributing personal belongings and assets, closing remaining accounts, and handling final taxes. Supporting family members emotionally and financially is also critical, as unexpected financial burdens can arise even with the best planning.

The best way to ease this process is by planning ahead. Having an updated will or trust, maintaining a list of financial accounts and key documents, using a password vault, and discussing final wishes with loved ones can help ensure a smooth transition. Regularly reviewing beneficiary designations on accounts and property is also essential to prevent unintended complications.

While this is a difficult conversation, taking steps now can relieve significant stress later. If you need guidance, Thimbleberry Financial can help.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

The 83(b) Election allows recipients of stock grants to pay taxes on the stock's value at the time of the grant rather than waiting until it vests. If the stock appreciates over time, this decision can result in substantial tax savings, as the taxable income is locked in at a lower rate. However, it’s not always the best choice, and there are key risks to consider. Once the election is made, it cannot be reversed, and the taxes must be paid upfront, regardless of future stock performance.

Amy walks us through a real-world example with a hypothetical client, Emily, a software engineer who receives 10,000 shares of restricted stock. If she files the 83(b) Election when the shares are valued at $1 each, she pays taxes on $10,000. Four years later, if the stock is worth $10 per share, she avoids paying income tax on $100,000 when the stock vests, benefiting from long-term capital gains treatment instead. Without the election, she would be taxed on the stock’s higher value at vesting, potentially leading to a much larger tax bill.

We also discuss how 83(b) applies to stock options using another hypothetical client, Mark, a doctor in the healthcare field. If Mark exercises his options early while the stock is at $2 per share and files an 83(b) Election, he eliminates the income tax liability at vesting and benefits from capital gains treatment on future gains. Without filing, he would owe income tax on the difference between the strike price and the stock’s value at vesting, which could lead to a massive tax burden.

However, the 83(b) Election is not for everyone. Key risks include leaving the company before stock vests, the stock declining in value, or not having the cash available to pay the upfront tax. Timing is also critical—filing must be completed within 30 days of the grant or exercise, with no exceptions. The process involves submitting a signed election form to the IRS via certified mail, providing a copy to the employer, and attaching the form to the tax return for that year.

Ultimately, the 83(b) Election can be a powerful tax-saving tool, but it requires careful consideration. If you’re receiving stock as part of your compensation, understanding this option and consulting a financial professional can help determine if it’s the right move for you.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

At the same time, adult children often think their parents only want to talk about maintaining independence or that they’re unwilling to discuss financial matters. In reality, many parents want to share their wishes but struggle with how much detail to provide. Some are hesitant because they fear their preferences may be ignored or overridden. Others want to pass on their financial values, ensuring their wealth is used to support family members or causes they care about.

The key to bridging these communication gaps is to approach the conversation with curiosity rather than control. Keeping discussions casual and starting with shared goals—like ensuring the family is prepared—can help ease tension. If starting the conversation feels awkward, using a real-life example (or even a made-up one) can make it more natural. A financial professional can also be a valuable resource in facilitating these discussions, helping to clarify complex topics like estate planning and long-term care preferences.   Amy explains how this might work.

A structured yet informal family meeting with a financial advisor can ensure that everyone understands the financial landscape, responsibilities, and expectations. Whether it’s deciding who will handle the bills, managing digital assets, or simply settling who gets a sentimental ceramic cat, these discussions help eliminate surprises and prevent misunderstandings down the road.

The bottom line: these conversations don’t have to be overwhelming. By starting small, approaching with curiosity, and focusing on shared goals, families can navigate aging and financial planning with confidence. And if it all feels too daunting, professionals like Amy Walls at Thimbleberry Financial are available to help guide the process.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Amy highlights the seamless integration of technology into their services. Through secure platforms like Microsoft Teams, they maintain interactive sessions where screen sharing and real-time guidance ensure clients remain engaged and understand every aspect of their financial plans. This virtual method also allows for greater flexibility, enabling clients to meet from home, work, or even while traveling within the U.S.

Despite initial misconceptions, Amy dispels the myth that virtual advising is less personal. She emphasizes that trust, communication, and understanding—not physical proximity—build connection. Clients still receive the same personalized care and attention, from initial consultations to ongoing check-ins. The virtual format even enhances convenience, as meetings can adapt to clients’ schedules without the burden of commuting.

Amy recounts how the virtual model benefits clients, particularly busy professionals, who appreciate the efficiency of hopping into meetings without interrupting their day. She also notes the technology’s role in maintaining client relationships even when they relocate, a challenge in pre-pandemic times.

For anyone hesitant about the virtual format, Amy assures listeners that technology simplifies the process without sacrificing the personal touch. Thimbleberry Financial’s approach is designed to integrate seamlessly into clients’ lives, helping them achieve their financial goals confidently and efficiently.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

We begin by addressing their primary goal: replacing Stan’s paycheck as he retires. Given their modest spending of $100,000 annually, the focus is on balancing stability, flexibility, and efficiency. Strategies include leveraging Stan’s Social Security at age 70, drawing from qualified accounts to manage required minimum distributions (RMDs), and addressing the 10-year fixed distribution requirements from certain accounts. Consolidating multiple accounts into a single IRA for administrative simplicity is another point of emphasis.

Once income is stable, we explore aligning their investments with their goals. A mix of bond ladders, dividend-paying stocks, and liquid investments ensures consistent income while managing risk. We emphasize a conservative-to-moderate approach for near-term needs, with some growth-focused investments to combat inflation and support their longer-term financial stability.

Taxes play a significant role, and we discuss strategies like Roth conversions before Stan’s RMDs begin, allowing funds to grow tax-free for future needs. Charitable giving through Qualified Charitable Distributions (QCDs) and donor-advised funds offer opportunities to support causes while reducing taxable income. For family, gifting up to $19,000 per year per recipient tax-free enables Stan and Jan to enjoy seeing their loved ones benefit from this money during their lifetime.

Ultimately, this case study highlights that retirement planning is about more than just numbers—it’s about aligning financial strategies with personal values and creating a fulfilling, stress-free retirement. Whether simplifying accounts, managing taxes, or crafting a legacy, thoughtful planning helps ensure a meaningful and secure future.  Having "enough to retire" may only be the first piece of the puzzle.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

The first step is assessing financial security. We discuss the importance of emergency savings—understanding how many months of expenses are covered in cash and adjusting based on job risk. Fixed versus variable expenses come next, distinguishing between unavoidable costs like mortgages and flexible spending like entertainment or dining out. Debt management is another key area, ensuring that individuals understand their obligations, interest rates, and potential flexibility in payments.

Beyond immediate financial security, we talk about the importance of understanding job stability. If layoffs or funding cuts are on the horizon, it’s crucial to be proactive—whether that means increasing savings, cutting non-essential spending, or exploring additional income sources like consulting or teaching. Healthcare coverage is another major consideration, and we encourage listeners to research COBRA, marketplace insurance, or partner coverage options before a crisis hits.

For those already facing job loss, prioritizing cash flow is essential. Cutting unnecessary expenses, filing for unemployment, negotiating with lenders, and leveraging professional networks can help mitigate financial strain. We emphasize the importance of staying connected—networking can lead to unexpected opportunities.

Finally, long-term financial planning remains critical. Maintaining a flexible budget, keeping emergency savings replenished, and ensuring retirement investments align with financial security goals all contribute to financial resilience. Having an updated resume and staying aware of career opportunities can make transitions smoother if funding cuts impact employment.

The key takeaway: focus on what you can control. By taking small, proactive steps each day, researchers and professionals can navigate uncertainty with confidence.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Amy shares that her early exposure to financial advising came from her father, who was a financial advisor until his passing when she was six. Although she initially strayed from the path, working in nonprofit management and fundraising, Amy became disillusioned with the inefficiencies she witnessed in the nonprofit space. This led her to soul search for a profession where she could have greater influence and deliver meaningful results. After years of self-assessment, Amy embraced her calling as a financial advisor, driven by a passion for empowering others with clear direction and support.

Amy specializes in tech and healthcare clients. and each group faces unique challenges. For tech clients, Amy emphasizes the complexity of equity compensation, tax implications, and the "noise" of unsolicited advice within the industry. These clients often need help navigating inconsistent income streams and making personalized financial decisions. In healthcare, professionals face challenges such as complex tax scenarios, underutilized employer benefits, delayed wealth accumulation due to extended education (and loans), and societal pressures to maintain a high-cost lifestyle. Amy highlights the importance of tailored financial strategies to address these multifaceted issues.

Amy's approach at Thimbleberry Financial focuses on educating clients, simplifying complex financial concepts, and creating plans that align with individual goals and values. Her team emphasizes trust, a judgment-free environment, and actionable guidance, enabling clients to feel confident and supported. Whether it’s saving a client from significant tax penalties, helping them navigate unexpected early retirement, or enabling tech clients to take self-funded sabbaticals, Amy finds deep fulfillment in making a tangible impact.

Amy concludes by sharing her ultimate goal for her clients: to feel confident, supported, and empowered in their financial journeys. Through trust, connection, and education, Thimbleberry Financial aims to provide clients with clarity and peace of mind, ensuring their financial plans align with their personal values and future aspirations.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Amy begins by explaining what a HELOC is—a line of credit secured by the equity in your home that operates much like a credit card, but with a variable interest rate and lender-imposed limitations. Unlike cash in the bank, which is liquid and entirely within your control, a HELOC is borrowed money subject to lender discretion. Amy recalls the 2008 financial crisis when many lenders reduced or froze HELOCs due to economic downturns. If a HELOC were someone's sole cash reserve, they might find themselves without access to funds when they need them most.

There's also the unpredictable nature of HELOCs. Factors like interest rate variability, declining home values, or personal credit score changes can make repayment more expensive or render the HELOC inaccessible. Relying on this type of borrowing creates new debt, adds to monthly financial burdens, and can even endanger your home if you're unable to make payments.

Amy emphasizes the importance of building a liquid cash reserve as the cornerstone of financial planning. She advises saving three to six months' worth of living expenses in a savings or money market account. This cash reserve acts as a financial "life jacket," offering immediate access to funds during emergencies without incurring debt or lender restrictions.

While a HELOC should not serve as a cash reserve, Amy acknowledges it can have a place in a financial plan. For example, it can be a useful tool for home improvement projects, provided it is used strategically and repaid responsibly. A cash reserve is like a life jacket and a HELOC is like a paddle—both valuable, but with distinct purposes.

You should approach emergency funds with a clear purpose. Start small, save consistently, and remember that a solid cash reserve is the foundation of financial stability. A HELOC, while useful in certain scenarios, is not a replacement for cash.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Amy Walls begins by discussing the challenges of maximizing tax-advantaged contributions. She emphasizes the importance of building habits, likening it to brushing your teeth or exercising. A gradual increase—like raising 401(k) contributions by 1% each month—can make these adjustments manageable and sustainable. Small, consistent actions build financial momentum.

Next, we tackle stock options and RSUs, particularly for those in the tech sector. Amy recommends diversifying holdings to avoid placing all financial eggs in one basket. Planning how to reinvest proceeds from selling stock in advance can help manage the emotional hurdles of timing sales. She advises consulting trusted individuals with relevant experience and reframing decisions as part of a larger financial strategy.

For those with excess cash flow, Amy suggests breaking large decisions into smaller, less intimidating steps. Like planting a garden, starting small with investments and building over time allows for control and adaptability. Monthly transfers, for example, can help build confidence without feeling overwhelming.

Estate planning is another key area where procrastination reigns. Amy advises creating annual check-ins and starting small—like updating beneficiary designations—to make progress feel less daunting. Life changes happen frequently, making regular updates essential to ensure alignment with current goals.

We also explore the art of meaningful giving, whether to charities or family. Simplifying the process—such as focusing on a few causes or using donor-advised funds—can make giving more impactful and less stressful. Transparent family conversations around financial goals can further reduce misunderstandings.

Finally, we discuss achieving better work-life balance by prioritizing personal goals with the same importance as professional ones. Amy shares her own experience of scheduling personal tasks, like watering plants, alongside work obligations. She emphasizes making vacation planning and funding non-negotiable and leveraging delegation to minimize stress.

The overarching message is that financial success in 2025 depends on small, consistent changes, intentional planning, and balancing priorities. For personalized support, we encourage you to connect with Thimbleberry Financial, below.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

We start by tackling the sensitive topic of debt. Amy shows us her “suitcase” analogy to explain tailoring financial discussions to a child’s age and capacity. Younger children benefit from relatable examples like borrowing toys or Halloween candy trades to grasp the basics of borrowing and repayment. For older kids, it’s about introducing concepts like credit cards, interest, and student loans while sharing real-life stories to provide context.

Next, we cover budgeting, where Amy suggests turning it into a game. She shares how activities like shopping for a food drive or handling a pretend shopping trip can teach kids about choices and trade-offs. By guiding children through small financial goals and allowing them to make mistakes in a controlled way, they learn the value of planning and accountability.

Amy also emphasizes the importance of generosity. She explains how encouraging kids to give, whether through charitable donations or thoughtful gift-giving, can foster a sense of responsibility and connection. She suggests matching their contributions to amplify the impact and reinforce positive habits.

When it comes to investing, Amy recommends starting with simple concepts. For example, using well-known companies like Disney or Apple can make stocks relatable. Analogies, like planting a tree to illustrate the slow growth of investments, help demystify the process. However, she stresses the importance of having a solid cash reserve before diving into investing.

Jg and Amy reflect on how money conversations were often avoided in previous generations. By fostering open discussions and age-appropriate financial lessons, parents can better prepare their children for a healthy financial future.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Amy shares how her own family balances this by distinguishing between routine chores, which support the family, and additional tasks that can earn money. This system, which includes "bonus jobs" for extra earnings, teaches kids the value of effort and money while avoiding a sense of entitlement. The conversation also touches on how to engage young kids in financial learning. For example, letting them handle cash or count coins at an early age makes money more tangible. Jon and Amy agree that relying solely on credit and debit cards can obscure the concept of money, not only for children but for adults as well.

One particularly memorable anecdote involves Amy’s son learning to budget while shopping for a food drive. This hands-on experience with a limited budget helped him understand the importance of stretching dollars to maximize value. As kids grow older, parents can introduce more complex financial lessons, such as saving a portion of birthday money or learning to budget for personal expenses like clothes. These lessons can be tailored based on the child's age and developmental stage.

Amy also explains how she uses personal experiences, such as her own childhood encounter with buyer's remorse, to teach her kids about the emotional aspects of spending and saving. In addition, Jon and Amy discuss visual tools like clear jars labeled “save,” “spend,” and “share,” which can help younger children grasp the concept of managing money. For older kids and teenagers, opening a savings account or tracking spending through a debit card is recommended. Amy’s daughter, for example, learned a valuable lesson when she accidentally purchased a video game multiple times, illustrating the importance of monitoring bank accounts and understanding the consequences of online purchases.

Overall, Jon and Amy highlight the importance of being intentional and adaptable when teaching kids about money. Every family and child is different, so it’s about finding the right balance and approach that works for your situation.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

The first point Amy makes is that understanding the details of the offer is essential. It’s not just about a severance payment; early retirement packages might also include healthcare benefits, stock options, and other perks. A deep dive into these aspects is necessary to fully understand the implications, especially regarding taxes and retirement accounts. For example, lump-sum payments could push someone into a higher tax bracket, impacting overall cash flow. Additionally, unvested stock options and healthcare subsidies could significantly affect the offer's true value. Therefore, thoroughly reviewing the package over time ensures that all questions are addressed before making a decision.

Amy also discusses evaluating the risks of turning down an offer, such as the possibility of forced retirement or layoffs in the near future. For some, making the decision themselves—rather than waiting for the company—can provide a greater sense of control and ease of mind. We also explore the financial side: big payouts often mean big taxes, and drawing from retirement accounts prematurely could result in penalties. Amy explains that, for some clients, continuing to work may not improve their retirement outlook due to the high tax burden on their income.

Beyond the financial, the emotional aspect of this decision is key. Amy emphasizes the importance of aligning the offer with personal lifestyle goals. Is this a chance to change careers, pursue a passion project, or even relocate to be closer to family? For some, taking the offer can provide a sense of relief and new opportunities, while for others, the sacrifices may not be worth it.

Ultimately, the decision to accept or decline an early retirement offer should be made with long-term happiness in mind. It’s not just about the money—it’s about living the life you want, both now and in retirement. Amy advises listeners not to let fear drive the decision and to seek expert guidance to navigate these complex choices.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Once you’re financially independent, the next phase is about bringing together a team of professionals—a financial advisor, tax advisor, and estate planning attorney. These experts help create a strategic plan tailored to your specific financial situation and goals. Amy explains that intergenerational wealth-building strategies should focus on both tax efficiency and long-term growth, which often means taking a more aggressive investment approach with money earmarked for future generations.

Several financial tools can assist in this process. Amy mentions 529 plans for education, Roth IRAs for tax-free growth, and even life insurance policies that pass wealth tax-free. These instruments provide flexibility and potential tax advantages that help protect and grow wealth over time.

A significant aspect of wealth-building is education and passing down financial wisdom. As Amy points out, financial literacy is just as important as the money itself. Teaching children and grandchildren how to manage money responsibly, giving them opportunities to practice, and allowing them to make mistakes are crucial for ensuring that the wealth you’ve built doesn’t get squandered by future generations.

We wrap by emphasizing the importance of legal protections, such as insurance and estate planning, to safeguard wealth. From umbrella liability policies to updating estate plans regularly, it’s essential to have the right protections in place to ensure that your wealth transfers smoothly and securely when the time comes.

Amy encourages listeners to start planning today, whether they’re still in the dreaming phase or ready to take action, and to seek professional help to feel more confident in their decisions.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

On the other hand, financial advice, or financial planning, takes a broader and more comprehensive approach. It encompasses every aspect of a person’s financial life, from budgeting and cash flow to debt management, tax planning, retirement, and estate planning. Amy highlights that financial planning is about creating a roadmap tailored to individual goals and life circumstances. It's not just about managing investments, but rather helping people make smarter financial decisions across all aspects of their life, ensuring their puzzle pieces—such as income, taxes, healthcare costs, and family goals—fit together to create a cohesive financial picture.

The conversation further explores the importance of looking at long-term financial health. While investment advice can grow wealth, Amy emphasizes that without a financial plan, people might miss out on maximizing their financial potential or addressing risks like healthcare costs or tax inefficiencies. Financial planning adds purpose and intentionality to the money management process by linking investment strategies to broader life goals. This holistic approach is key for most people, as few live their lives in silos, and their financial decisions are deeply interconnected.

While investment advice serves those with specific portfolio management needs, financial planning offers a complete, integrated approach for those with broader, more complex financial goals. Amy underscores that most people would benefit from financial planning due to the interconnected nature of life and money.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Next, we tackle the myth that retirees will naturally spend less. While some costs like commuting might decrease, other expenses like travel, hobbies, and particularly healthcare, often increase. The Bureau of Labor Statistics reports that households led by those 65 or older still spend an average of $48,000 annually, suggesting that retirement spending is not always significantly lower than during working years.

We then discuss the misconception that retirees should avoid stocks to protect their savings. Amy challenges this idea, pointing out that retirement often spans 20-30 years. Having stocks in a diversified portfolio can be essential to outpace inflation and maintain purchasing power. Reducing stock exposure too drastically can actually increase the risk of losing value over time.

Another myth we address is the notion that retirees can always return to work if they run out of money. While it might seem like a safety net, factors like age, health, and the ability to find suitable work can make this option less reliable than people believe.

 Finally, we debunk the myth that it's too late to start saving for retirement. Amy emphasizes that even late contributions can grow significantly through compound interest and make a meaningful difference in retirement planning. Jag adds that retirement is a long period of time, not just a line in the sand.

In closing, Amy reminds listeners that small, consistent efforts toward saving and planning can improve their financial future, regardless of their starting point. As always, the advice here serves as a guide, but consulting with a financial professional is key to personalized retirement planning.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

The first myth we tackle is the belief that you need $1 million to retire comfortably. Amy explains that while this is often thrown around as a benchmark, the reality is far more nuanced. Retirement comfort depends on various factors like social security, pensions, and personal expenses. Many retirees live well on less than $1 million, provided they have a balanced financial plan and modest needs. Everyone’s situation is different, and it’s important to consider your own income sources and expenses, rather than focusing on an arbitrary number.

Next, we explore the idea that retirement means never working again. Amy highlights that many retirees continue to work part-time, start businesses, or freelance to stay active and fulfilled. In fact, 56% of retirees plan to work in some capacity after retirement, according to a Transamerica study. Interestingly, however, studies show that those who make a clean break from work tend to be happier in retirement. The trick is finding purpose, whether through work, volunteering, or family.

We also address the common belief that downsizing your home will always save money. While this might seem like a logical step, it doesn’t always pan out financially. Real estate fees, moving costs, and potential renovations in the new home can eat into savings. Additionally, many retirees find themselves emotionally attached to their homes, especially when considering family gatherings or memories, making downsizing less appealing or practical.

Another popular myth is that all debt should be paid off before retirement. While it’s a comforting idea to enter retirement debt-free, it’s not always necessary or even beneficial. Amy notes that paying off debt might require large withdrawals from retirement accounts, which can lead to significant tax consequences. Instead, it’s important to assess your cash flow, the interest rates on your debt, and whether paying it off makes sense in the bigger picture.

Finally, we debunk the notion that Medicare will cover all healthcare costs. While Medicare is essential, it doesn’t cover everything. Gaps like long-term care, dental, and vision expenses can add up, with retirees needing an estimated $315,000 to cover healthcare costs. It’s crucial to plan for these expenses early and consider supplement plans or health savings accounts.

In our next episode, where we’ll tackle five more retirement myths.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Amy explains that dollar-cost averaging helps mitigate risk by buying more shares when prices are low and fewer when prices are high, thereby balancing the overall cost. This strategy is particularly useful for those wary of market volatility. On the other hand, lump sum investing can yield higher returns as it gets the money working in the market immediately, a point backed by research from Vanguard which shows that lump sum investing outperforms DCA 68% of the time over one-year and ten-year periods.

We discuss why an investor might choose one strategy over the other. Lump sum investing offers simplicity and higher potential returns but comes with the risk of market downturns right after the investment. Dollar-cost averaging, while potentially yielding lower returns, reduces this risk and provides psychological comfort, preventing panic in the face of market drops.

Jag and his wife employ both strategies. She invests consistently each month through her 401(k), embodying dollar-cost averaging, while Jag, as a self-employed individual, saves throughout the year and make a lump sum investment into his SEP IRA at year’s end.

Market conditions also play a significant role in choosing a strategy. In a bull market, lump sum investing tends to perform better as the market is generally rising. During volatile or bear markets, dollar-cost averaging can be advantageous as it allows investors to benefit from lower prices over time.

Amy highlights historical performance, noting that lump sum investing generally yields more over a 10-year period, with 66-67% success across various markets like the US, UK, and Australia. However, risk-averse investors, or those who need time to adjust psychologically to seeing their cash reserves drop significantly, might prefer dollar-cost averaging.

Practical tips for deciding between these strategies include assessing personal risk tolerance, considering one’s financial situation and goals, avoiding market timing, and seeking professional advice. The key takeaway is that there’s no absolute right or wrong choice between lump sum investing and dollar-cost averaging. The best decision is the one that aligns with personal comfort and long-term financial objectives.

For further advice, listeners can reach out to Amy and her team at Thimbleberry Financial via their website or phone. It’s important to remember that investing should always be approached with a long-term focus and in consultation with financial professionals

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

We start by recognizing that emotions significantly impact our decisions. Amy shares a personal anecdote about her current dilemma in buying a new car, highlighting how fear and greed can influence our choices. These emotions, she explains, can cloud our judgment, making us second-guess our financial decisions even when we are financially capable.

Cognitive biases also play a crucial role. Overconfidence, anchoring, and confirmation bias can lead to poor decision-making. For instance, anchoring on a specific price point or seeking out information that supports pre-existing beliefs can skew our choices. Additionally, heuristics or mental shortcuts, like the outdated 4% rule for retirement withdrawals, can lead to oversimplified and potentially harmful financial strategies.

Amy emphasizes the importance of rational analysis and comprehensive data in countering these biases. She also stresses the value of delayed gratification, learning from past mistakes, and remaining adaptable. Jon and Amy discuss the benefits of having rational conversations, especially on polarizing topics like politics, to understand different perspectives and make informed decisions.

A significant point Amy raises is the concept of mental accounting, where people treat money differently based on its source or intended use. This can lead to irrational spending habits, such as splurging bonuses or inheritance money multiple times over.

On the flip side, good decision-making strategies include rational analysis, focusing on long-term benefits, and emotional regulation. Amy advocates for making decisions based on logic rather than impulse, and seeking the advice of experts to provide objective insights.

Amy shares practical tips to avoid common financial pitfalls. Panic selling during market downturns, chasing trends without proper research, and overconfidence in unfamiliar areas are major traps. To avoid these, she suggests having a long-term investment plan, staying disciplined, diversifying investments, and regularly reviewing one's financial strategy.

Finally, Jon and Amy conclude by stressing the importance of professional financial advice. Whether one is working with an advisor or managing finances independently, education, thorough research, and the use of technology for data-driven decisions are key. Balancing the science of financial data with the art of human behavior is essential for successful financial management.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Amy explains that increased volatility is a major risk factor. A portfolio with fewer assets is more susceptible to large swings in value based on the performance of those assets. For instance, if a single asset makes up 25% of the portfolio and its value drops significantly, the entire portfolio suffers. This risk is compounded if the concentrated asset belongs to a single company or industry, which can be affected by negative news, regulatory changes, or industry-specific challenges.

Jag and Amy also explore the emotional stress associated with a concentrated portfolio. Significant fluctuations can lead to stress, resulting in impulsive decision-making, such as selling low during downturns. Amy highlights the importance of diversification in spreading risk and reducing the impact of any single investment’s poor performance. Without diversification, investors are essentially putting all their eggs in one basket, which can be dangerous.

To assess if their portfolio concentration is acceptable, Amy suggests investors ask themselves several questions. These include evaluating their financial and emotional ability to handle a significant loss, understanding their level of diversification, considering their time horizon for needing the money, and determining their stress tolerance for market fluctuations. Investors should also reflect on their understanding of the investment and its risks, how it aligns with their long-term financial goals, and their exit strategy if things don’t go as planned.

Behavioral finance plays a crucial role in investment decisions. Amy advises listeners to consider their reaction to market volatility, potential overconfidence in investment decisions, and biases such as anchoring, confirmation, and recency bias. It's essential to recognize tendencies to hold onto losing investments or be influenced by herd behavior. Additionally, Amy emphasizes the importance of simplifying decision-making processes and understanding how personal experiences influence behavior.

If investors decide their portfolio is too concentrated, Amy recommends several steps. These include immediate or gradual diversification, using tax-advantaged accounts to minimize tax impacts, considering exchange funds to pool concentrated stocks with other investors, employing hedging strategies, making charitable donations of concentrated stock, and seeking professional guidance.

In conclusion, Jon and Amy stress the importance of regularly reviewing portfolios and reassessing risk tolerance. Each individual’s situation is different, and risk tolerance can change over time. Staying flexible, open-minded, and informed is crucial for managing investment risks effectively.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Amy starts by explaining the signs of financial exploitation, such as unexplained withdrawals, sudden changes in spending patterns, and alterations in legal documents. These warning signs might indicate someone is trying to gain control over a senior's assets. Isolation from family and friends, as well as the sudden appearance of new friends or caregivers with a strong interest in finances, are also red flags.

Approaching the topic with parents can be challenging. Amy suggests starting these conversations early, even before there are signs of trouble. Regular check-ins can help normalize financial discussions and reduce anxiety. Empathy is key—approaching these conversations from a place of care and support rather than control. Setting clear agreements about when and how to get involved can prevent misunderstandings and ensure everyone is on the same page.

For senior listeners, open communication with their adult children is crucial to prevent exploitation. Statistics show that a significant number of seniors experience financial victimization, and regular discussions can help identify and stop abuse early. Seniors should also ensure their wishes are clearly communicated to avoid misunderstandings and ensure their intentions are honored.

Amy provides practical steps for both seniors and their adult children to make these conversations more effective. Organizing important documents, developing a financial plan, and using technology to monitor accounts and automate payments are essential measures. Regular reviews with or without a third party can keep everyone informed and prepared for any financial or health emergencies.

As we wrap up, the emphasis is on the importance of technology and communication. Technology offers great tools for managing finances, and maintaining an open and ongoing dialogue is crucial for building trust and ensuring financial security. Amy encourages starting these conversations early and being empathetic and respectful throughout the process. For those needing assistance, financial advisors and lawyers can provide valuable support and mediation.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Amy emphasizes that this concern often leads people to adopt an "ostrich" mentality, where they bury their heads in the sand to avoid facing daunting financial decisions. Jon adds that this behavior is a form of fight or flight, driven by fear and unfamiliarity. They agree that simply winging it can be a costly mistake.

We introduce a case study to illustrate these points. They discuss a hypothetical couple, both aged 60, with different types of savings: $40,000 in cash, $600,000 in taxable investments, $2 million in IRAs, and $200,000 in Roth accounts. They compare the financial outcomes of spending $85,000 versus $100,000 annually in retirement.

• For $85,000 in annual spending, the optimal strategy involves withdrawing 45% from taxable accounts and 55% from IRAs. 
• For $100,000, the best approach shifts to 60% from taxable accounts and 40% from IRAs. 

Deviating from these strategies, even slightly, can significantly impact financial outcomes. 

• Using the $85,000 strategy for $100,000 in spending could result in $400,000 less in available funds by age 95.
• Using the $100,000 strategy for $85,000 in spending could lead to $300,000 less.

The consequences are even more dramatic when retirees choose to withdraw 100% from either taxable accounts or IRAs. 

• Drawing solely from taxable accounts until depletion could result in $740,000 less by age 95. 
• Withdrawing entirely from IRAs could lead to $1.5 million less.

We underscore the importance of dynamic financial planning, which involves regular reassessment of one's strategy to adapt to changing circumstances and ensure efficiency. Amy concludes by stressing that thoughtful distribution strategies are essential not only for maintaining financial stability but also for achieving personal goals, whether it’s enjoying life, covering unexpected expenses, or leaving a legacy.

For listeners seeking personalized advice, Amy encourages reaching out to Thimbleberry Financial for guidance tailored to individual circumstances.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

We discuss the common pitfalls tech professionals encounter when managing equity compensation on their own, such as significant tax bills from incorrectly selling ISOs and inadequate diversification. Holding onto stock with the hope of future gains, only to see the stock price plummet, is a recurring issue. We stress the importance of understanding the tax implications and maintaining a diversified portfolio to mitigate risks associated with over-concentration in company stock.

Amy highlights that while tech professionals are experts in their fields, they often lack expertise in financial planning, underscoring the value of consulting financial advisors. Using tools like Excel and calendar apps to track vesting schedules and exercise options can help, but disciplined execution is crucial. We recommend leveraging digital tools to manage equity compensation effectively, but also emphasize the importance of human expertise.

Work-life balance is another critical topic. We advise setting boundaries and scheduling dedicated time for financial planning to prevent it from overwhelming personal life. For instance, Amy shares how she and her husband hold regular meetings to discuss financial matters, integrating this practice into their routine to ensure it doesn’t interfere with family time.

Lastly, we encourage tech professionals to balance their involvement in financial planning with delegation to trusted advisors. Staying informed and asking questions about their equity compensation strategies ensures they understand and agree with the advice they receive. We suggest working with advisors who specialize in tech and behavioral finance to align financial strategies with personal goals and risk tolerance.

In conclusion, effectively managing equity compensation requires a blend of personal involvement and professional advice. By staying organized, disciplined, and informed, tech professionals can maximize their financial opportunities while maintaining a healthy work-life balance

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

First, they address the myth "I'll spend less in retirement," discussing how retirement often brings new expenses, such as travel, hobbies, and healthcare, which may not decrease spending as expected. While fixed costs like mortgages might end, discretionary spending and healthcare needs can actually rise.

The second myth is the belief that being debt-free in retirement equates to reduced expenditures. Amy explains that having low-interest debts like mortgages during retirement isn't necessarily bad if the returns on investments exceed the interest rates, emphasizing the importance of financial planning over simply clearing all debts.

The conversation then shifts to the effectiveness of employer-sponsored retirement plans like 401(k)s and 403(b)s. Amy argues that merely saving the maximum in these plans may not suffice for a comfortable retirement due to factors such as investment choices, duration of savings, and the timing of retirement, highlighting the complexity of retirement planning.

The fourth myth tackled is the idea of downsizing homes in retirement. While some may intend to downsize, Amy points out that emotional attachments and the physical demands of moving often keep people in their current homes longer than planned, complicating the downsizing process.

Lastly, they debunk the myth that taxes will be lower in retirement, with Amy warning that retirement income can trigger higher taxes and health insurance costs under Medicare's IRMAA surcharges. She stresses the importance of strategic financial planning to manage these potential increases effectively. Jag asks about the possibility of tax increases in the coming years.

Throughout the podcast, Amy and Jag emphasize that effective retirement planning requires a holistic approach, considering not only savings but also spending strategies, tax implications, and personal circumstances to ensure financial stability and fulfillment in retirement. They conclude by reminding listeners to consider retirement as a phase requiring its own unique set of strategies and preparations

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

NQSOs allow employees to purchase company stock at a predetermined price but come with no preferential tax treatment, meaning they are taxed as ordinary income upon exercise. This straightforward taxation can seem appealing, but it necessitates a keen understanding of one's tax situation, especially in pivotal life moments such as receiving a spouse's bonus or facing unemployment.

A key strategy in managing NQSOs is knowing when to exercise them to minimize the tax burden, particularly during years with lower income. However, it's crucial to only exercise options when the stock's market price exceeds the exercise price, ensuring a financial benefit.

Further discussing diversification, Amy emphasizes that once the stock is acquired through NQSOs, it should be treated like any other asset in the portfolio. The strategy here involves not just holding onto the shares hoping for appreciation but planning their sale to align with broader financial goals such as funding children's education, planning for retirement, or aiding family members financially.

Amy also shared a success story of  "Emily," who leveraged her well-timed exercise of NQSOs to significantly advance her retirement plans and support her children's education, demonstrating the potent role these options can play in achieving financial independence and meeting family goals.

Conclusively, while NQSOs offer no direct tax advantages, their real value lies in strategic exercise and diversification, underscoring the importance of planning and professional guidance to avoid pitfalls and maximize potential benefits. Remember, it's not just about having the shares; it's about integrating them thoughtfully into your financial landscape to meet personal and familial aspirations.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Amy highlights the challenges people face when trying to envision their future, including fear of the unknown and the difficulty of imagining life changes. She shares personal stories to illustrate these challenges, such as her fear of financial independence after college (this contrasts with Jag's approach to college). We explore how different life stages, like becoming parents or transitioning to retirement, come with their own sets of fears and uncertainties.

The conversation then shifts to the importance of being clear about what we want in later life stages to avoid being unprepared financially. Amy stresses the value of having specific goals to motivate saving and planning for the future. We discuss how changing priorities or goals is natural and not problematic as long as there's a willingness to adapt and adjust financial plans accordingly.

Amy offers strategies for looking ahead and connecting with our future selves, such as setting aside time for contemplation, getting in touch with our values, and recognizing how today's choices impact our future. She shares personal anecdotes about preparing to enjoy activities with future grandchildren and the importance of taking care of oneself to maintain health and vitality in later years.

Finally, we touch on the concept of living in limbo and the stress it causes due to a perceived lack of control. Amy suggests finding at least one aspect of a situation that can be influenced or controlled as a way to navigate forward.   And as a bonus, you'll hear a couple of Shel Silverstein references.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Amy emphasizes the importance of timing for achieving a qualifying disposition. There must be at least one year between the grant and exercise dates, and another year between the exercise and sale dates, totaling a minimum two-year holding period. Failure to meet this timeline results in a disqualifying disposition, subjecting the profit to ordinary income tax rates.

Strategic planning is crucial for maximizing the benefits of ISOs. Amy suggests considering the market price when exercising options, as this can affect the alternative minimum tax (AMT). Exercising when the market price is low can minimize AMT, potentially leading to significant tax savings. She also advises against using shares to cover the exercise price, as this could lead to a disqualifying disposition.

Amy shares success stories of tech professionals who've strategically used ISOs to enhance their financial journey. One individual, referred to as Mark, meticulously planned his ISO exercises and holding periods, resulting in substantial long-term capital gains and contributing significantly to his financial independence. Another example involves Brenda, who initially hesitated to exercise her options during a market dip. However, after understanding the tax implications, she realized exercising more shares could save her $30,000 in taxes.

For tech professionals looking to incorporate ISOs into their retirement plans, Amy underscores the importance of planning and working with financial and tax professionals familiar with ISOs. Understanding the specifics of your company's ISOs and how they fit into your overall financial plan is essential. She also highlights the need to be aware of how shares will be treated at retirement, as some companies allow for continued vesting or immediate vesting upon retirement.

In summary, ISOs offer a valuable opportunity for tax-efficient growth and financial planning, but they require careful strategic planning and professional guidance to fully capitalize on their benefits.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Amy also tackles the topic of fees and performance, urging listeners to consider the value provided by a fund rather than just its expense ratio. A fund's net performance, after fees, is what truly matters. The conversation shifts to assessing fund performance, where Amy suggests using custodian-provided information and comparing it against benchmarks over various time frames. This approach helps in making informed decisions rather than chasing short-term gains.

The discussion addresses the risks associated with fund selection, including market volatility, inflation, interest rate changes, and the dangers of following unqualified advice from the internet. Amy advocates for a balanced approach to risk management through diversification and proper asset allocation. She also defends the use of target date funds, which can be a viable option for many investors, especially when other choices are limited or less appealing.

Finally, Amy advises on the frequency of reviewing and adjusting fund allocations, recommending at least an annual check-up to ensure alignment with one's financial goals and market conditions. This conversation underscores the importance of informed decision-making and seeking professional guidance when navigating the complexities of retirement fund selection.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Amy highlights the importance of being forward-looking in financial planning, contrasting with the backward-looking nature of tax preparation by CPAs. She advises setting aside a portion of RSUs or their proceeds to cover taxes, ensuring no surprises come tax time. Employers typically withhold a portion of the vested shares to cover federal taxes, with the remaining shares transferred to the employee's brokerage account, which can then be liquidated or managed according to the employee's financial strategy.

Success stories, like that of "Sarah," illustrate how effectively managing RSUs can significantly contribute to wealth building and achieving financial independence. By strategically selling vested shares to diversify investments, tech professionals can leverage RSUs as a cornerstone of their financial planning. However, it's crucial to avoid common misconceptions and pitfalls, such as the belief that holding RSU-derived shares for over a year qualifies them for preferential capital gains tax rates. In reality, RSUs are taxed as income upon vesting, and any decision to hold shares longer is akin to purchasing employer stock directly, with all associated risks.

Understanding RSUs' role in compensation and wealth building, while navigating their tax implications and avoiding common pitfalls, is essential for tech professionals looking to maximize their financial potential. Engaging with a financial professional can provide valuable guidance in managing RSUs effectively as part of a broader financial strategy.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Amy explains tax implications of inheriting investments, especially the step-up in basis, using an example to show how this works.

When evaluating an inherited investment portfolio, Amy's advice is simple: check if the investment fits your needs and how it performs against its peers. She uses direct examples to show how to approach inherited investments, considering risk tolerance and diversification.

The discussion shifts to the emotional side of inheriting investments, like stocks from a company with family loyalty. Amy suggests honoring the deceased in ways other than holding onto their investments. She proposes using the inheritance for family-oriented projects or supporting meaningful causes.

Not changing inherited investments has many risks. These include lack of diversification, mismatched risk profiles, tax inefficiencies, and altered savings needs.

On using inherited investments to support goals, Amy emphasizes clarity in goals and being aware of how they might change with new wealth. She advocates for a balance between saving for the future and enjoying the present.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

We compare ESPPs to 401k plans, highlighting the immediate financial gain from the discounts, which can be as high as 15%. We explain the typical structure of these plans, including offering periods and the mechanics of purchasing shares at a discounted rate. The specifics of these plans, such as the discount rate and the timing of stock purchases, are set by the employer.

Next. we cover the tax implications of ESPPs. While the discount is taxed as ordinary income, the real tax benefit comes when selling the shares. To maximize this benefit, shares should be held for at least one year after purchase and two years from the start of the offering period. This strategy allows gains to qualify as long-term capital gains, which are taxed at a lower rate than ordinary income.

We also explore strategies for making the most of ESPP participation. We advise contributing the maximum amount allowed and discuss the importance of selling shares strategically. We note the risk of stock volatility and the potential issue of being too financially tied to one's employer.

We share a real-life example of a client, who successfully used his ESPP to fund his children's college education and boost his retirement savings. This  illustrates the power of ESPPs as a tool for achieving various financial goals.

Finally, we discuss aligning ESPP participation with broader financial objectives. We stress the importance of understanding one's financial goals and how ESPPs can play a role in achieving them. You should consider your overall financial position and  level of investment in your employer's stock when deciding whether to sell or hold ESPP shares.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

The conversation then shifts to who can benefit from Roth accounts. While lower income brackets are often considered ideal candidates, high-income earners also stand to gain significantly, provided they approach it strategically. She outlines the income limits for Roth IRA contributions, highlighting the differences for single and married filers and the additional contributions allowed for those over 50.

Amy and Jag discuss the SECURE Act 2.0 and its implications for Roth accounts, including the new provision allowing employer matches in 401ks and 403bs to be directed towards Roth accounts, and the delayed implementation of a rule mandating catch-up contributions to be made to Roth accounts, starting in 2026.

The conversation then explores various strategies for high-income earners to maximize their Roth contributions, such as backdoor Roth conversions and after-tax contributions to employer plans. Amy stresses the complexity of these strategies and the importance of understanding their tax implications.

Regarding optimizing Roth investments, Amy advises high-income earners to consider aggressive (but within their risk tolerance) investment strategies within their Roth accounts due to their tax-free nature. She also touches on the importance of regular portfolio reviews and being mindful of tax-efficient investing.

Finally, there are limitations and pitfalls of using Roth accounts, such as income phase-out limits and tax consequences of improper conversions. Amy emphasizes the need for careful planning and awareness of contribution limits and deadlines. We also highlight the tax planning benefits of Roth accounts, including their role in estate planning and the flexibility they offer in managing future tax brackets.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Amy highlights three major challenges tech professionals face regarding equity compensation: time, knowledge, and access to accurate and up-to-date resources. She emphasizes that tech professionals often lead demanding lives, balancing intense work schedules with personal commitments, which leaves little time to manage personal finances effectively. This is particularly relevant in the context of 2023, which saw significant layoffs and increased work demands in the tech industry.

The conversation then shifts to the importance of knowledge in managing equity compensation. Amy uses an analogy of baking, comparing the complexities of equity compensation to the intricacies of baking a complex recipe. She points out that while some aspects of equity compensation might be straightforward, integrating multiple elements such as various forms of equity compensation, taxation, and investment options can be challenging.

The third challenge discussed is the need for accurate and up-to-date resources. Amy notes that tech professionals, being problem solvers, often rely on internet research or advice from colleagues, which may not always be reliable or applicable to their specific situation. She stresses the importance of seeking professional financial advice to navigate these complexities.

Amy suggests that while there are tools available to manage equity compensation, simplicity is key. She recommends basic tools like Excel spreadsheets and calendar apps, combined with discipline and familiarity with employer-provided documents, to effectively manage equity compensation.

Tech professionals should seek out financial advisors who specialize in equity compensation. She emphasizes the importance of professional advice in navigating the complexities of equity compensation and achieving financial goals. 

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

First, celebrating these milestones motivates individuals and gives them a sense of accomplishment. It acknowledges the hard work and dedication that goes into achieving financial goals. This recognition acts as a powerful motivator to continue striving towards financial aspirations.

Secondly, celebrations reinforce positive financial behaviors and habits. When people see the results of their sound financial decisions, it encourages them to keep making wise choices. This helps maintaining disciplined saving, investing, and planning for the future.

We also cover the psychological benefits of celebrating financial successes. These celebrations boost self-esteem and confidence, validating individuals' financial decisions and choices. This validation enhances their sense of security about their financial future. Moreover, celebrating these milestones helps develop a positive money mindset, which is essential for long-term financial success.

Celebrations also create a sense of fulfillment and well-being, allowing individuals to reflect on their progress and appreciate how far they've come. This reflection can significantly reduce stress and anxiety related to financial matters. Additionally, these celebrations foster a sense of gratitude and happiness, encouraging a positive outlook that can influence other areas of life.

Amy suggests various ways to celebrate these milestones, from simple dinners with loved ones to more elaborate events like special trips or charitable donations. The key is to choose a celebration method that aligns with one's values and is appropriate for the milestone.

We should set both big and small financial goals and to celebrate these achievements as they come. These celebrations are not just about acknowledging progress but also about reinforcing positive financial behaviors. 

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Prince's estate faced a lengthy legal battle due to the absence of a will, despite having a Revocable Trust. Similarly, Aretha Franklin's lack of a will or trust led to potential disagreements among her heirs and increased estate taxes. These examples highlight the consequences of not having proper estate planning documentation.

The first step in legacy planning is setting clear expectations with loved ones and ensuring that one's will or trust is legally sound and reflective of their desires. This helps avoid misunderstandings and conflicts.  Amy compares trusts with wills, explaining the benefits of trusts, such as privacy, probate avoidance, control over asset distribution, and safeguarding one's practice. Trusts, unlike wills, remain private and allow for direct distribution of assets to beneficiaries without court intervention. Trusts also provide more flexibility in how assets are distributed and can be particularly useful in protecting a healthcare practice.

An unfunded trust, like Prince had, lacks assets, which are necessary for the trust's instructions to apply. Other common mistakes in legacy planning, such as failing to update estate plans regularly and not considering tax implications, as seen in the cases of Philip Seymour Hoffman and James Gandolfini.

We aren't all gloom and doom today, however. Amy shares success stories of healthcare professionals who effectively planned their estates, ensuring smooth transitions of their practices and creating lasting impacts through charitable foundations or scholarships. The power of legacy planning and the importance of organizing financial affairs benefits loved ones and the profession.

To get in touch with Amy and her team at Thimbleberry Financial, listeners can reach out by calling 503-610-6510 or visiting thimbleberryfinancial.com.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Amy emphasizes the importance of combining financial planning and wealth management. Financial planning is not solely about investment management.She highlightsthe various elements involved, such as goal identification, cashflow, debt management, insurance, real estate, education, retirement, estate planning, and taxes. All of these components are like pieces of a puzzle, with each piece interlocking to create a complete financial picture.

In discussing the challenges of managing multiple financial goals, Amy provides a real-life example of someone wanting to buy a new home while planning for early retirement. She explains how the integration of financial planning and wealth management allows them to navigate complex situations, ensuring that all financial pieces work together harmoniously.

Jag raises the question of what happens if a client prefers one service over the other. Amy emphasizes the importance of educating clients and guiding them toward making informed decisions that align with their financial goals. If a client remains set on one specific approach, Amy is open to referring them to other advisors who may better suit their preferences.

Costs in financial advisory services vary widely, and Amy clarifies that Thimbleberry Financial has a transparent fee structure, charging separately for financial planning and wealth management. She highlights the value of saving clients time by integrating these services, as it allows for a one-stop, comprehensive approach to financial decision-making.

Jag shares his own experience transitioning from a wealth manager to an advisor like Amy, appreciating the ability to have more encompassing conversations about the implications of various financial decisions. Amy adds that Thimbleberry Financial's ideal clients are retirement-focused professionals in healthcare and tech sectors, who value financial independence and holistic financial planning.

Regarding client communication, Amy explains Thimbleberry's team-based approach, with dedicated service teams working closely with clients to ensure smooth and efficient communication. The episode concludes with a shout-out to Sara, Amy's Chief of Staff, who plays a crucial role in podcast production and client relations.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Amy explains that protection isn't just about insurance, although that's a significant part of it. It encompasses various forms of insurance like life insurance, disability insurance, long-term care insurance, and more. For healthcare professionals, malpractice insurance is also a critical component.

Amy then explains the different types of accounts where your money is held, and the varying levels of protection they offer. Amy emphasizes that under the Employee Retirement Income Security Act (ERISA), employer-sponsored retirement plans, such as 401(k)s, enjoy robust protection against creditors, even in bankruptcy situations. State rules come into play for IRAs, and their protection can differ significantly, so understanding your state's regulations is vital.

The discussion then touches on IRAs, and Amy explains that while they have some federal bankruptcy protection, there's a cap on this protection, which can vary depending on factors like inflation adjustments. If you're transferring assets from a 401(k) to an IRA, the key is not to commingle rollover assets with contributions, maintaining the federal protection.

The conversation shifts to traditional insurance types like life insurance and disability insurance. Amy distinguishes between term and permanent life insurance, highlighting that term insurance is cost-effective for temporary needs, while permanent insurance is more expensive and intended to last a lifetime.

On the topic of disability insurance, Amy stresses the importance for healthcare professionals, as the risk of disabilities affecting their ability to work is substantial. She also points out that disability insurance can become more expensive with age, and it's statistically more expensive for women.

Really, employees in any field (even podcast production) can face financial challenges if they become unable to work, emphasizing the need for disability insurance.  

Protecting your assets also involves considering long-term care insurance, ideally by age 60. Planning early is key, given the time required to assess care needs and preferences. Amy advises evaluating other assets that could cover these expenses and whether competing interests, like leaving assets to family members, affect your choices.

We finish up with malpractice insurance, which is crucial for healthcare professionals, and the significance of umbrella insurance to protect against potential liability claims, especially for high-income individuals. 

For more, reach Thimbleberry Financial 503-610-6510  or at https://thimbleberryfinancial.com/

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Simply put, an ISO is a type of employee stock option that comes with tax advantages.  No income tax is due when options are granted or exercised. Also, profits from the sale of ISO's can be taxed under more favorable long-term capital gains rates, provided certain conditions are met.

In addition to those restrictions around time of holding, Amy also explains the Alternative Minimum Tax, or AMT.  When do you pay AMT, and what AMT implications should you consider when exercising ISO's?

We also walk through vesting, expiration, and post termination.

Being proactive and creating a plan is key in this realm; there are certain decisions and actions that cannot be undone.  Amy explains the $100k rule and the Rule of 65, and she cautions against being overweighted in company stock, particularly in the context of market volatility.

For more information contact Amy Walls and her staff at 503-610-6510 or click here Thimbleberry Financial.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Amy walks us through the hurdles of having separate business entities, sometimes earning income in different countries with different rules.   Regardless, its critical to keep good records and often advantageous to work with  a Certified Public Accountant, or CPA.   This can be helpful with understanding deductions and what you are eligible for.

Amy's specialty is retirement planning.  Because traditional retirement plans have dollar limits, those limits can often represent a smaller percentage of income for higher wage earners.    These individuals may want to look into other retirement vehicles, such as 457 plans and saving into nonqualified, taxable investmets.  We dive into the latter.

Amy and Jag wrap up, we cover a few other tax strategies, including tuition benefits, student loan forgiveness, and chartiable giving.

For more information contact Amy Walls and her staff at 503-610-6510 or click here Thimbleberry Financial.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

We cover the financial considerations of taking a six-month break. Amy's practical approach navigates the complexities of maintaining financial stability during a career transition. The discussion also delves into the intricate balance between staying for vested equity and pursuing a career break.

Benefits, equity, and health insurance are dissected as critical components of career transitions. Amy and JAG explore the nuances of leaving a current job, considering the impact on benefits, equity compensation, and insurance premiums. The hosts examine the financial implications and practical aspects of these decisions.

Non-financial aspects are also explored, including the potential impact of resume gaps and the significance of planned time usage during a break. The hosts delve into the long-term considerations of career breaks and sabbaticals, inviting listeners to approach these decisions thoughtfully.  Keep in mind, you'll likely spend more every week and month when you're not working!

As always, It's important to place an emphasis on the significance of intentional decision-making tailored to individual circumstances. 

For more information contact Amy Walls and her staff at 503-610-6510 or click here Thimbleberry Financial.
 

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Risk tolerance is also a key factor to consider, as it determines an individual's comfort level with market fluctuations. Jag points out that your "theoretical" risk tolerance may not translate to what you actually feel when the market becomes volatile.

Amy explains the tax implications of different investment options, such as retirement accounts and tax-free investing. She also addresses the concept of ethical and social investing, highlighting the need to align investments with personal values. That said, beware the idea of "emotional investing."  If you have particular companies you believe in, consider a smaller "fun" investment account, as opposed to betting your retirement on them.  

We conclude by discussing the costs and fees associated with various investment options and the importance of adjusting investment strategies over time.

For more information contact Amy Walls and her staff at 503-610-6510 or click here Thimbleberry Financial.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Naturally, the first step is to categorize your needs vs your wants. Needs include housing, transportation, and utilities.  Wants are more discretionary, like entertainment, hobbies, and dining out.   But it is important to know that a want can become a need.  For example, a vacation home may be a want, but after you buy it, the monthly bills become a need.

Saving 20% of your income can make a major difference in your financial future.  This can be done through retirement plans, emergency savings, and more.

Finally, we talk about how to overcome some common challenges faced by busy professionals when they try to create a budget.

For more information contact Amy Walls and her staff at 503-610-6510 or click here Thimbleberry Financial.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Key Takeaways:

• Smart money management is a skill that can be developed, and physicians need to prioritize saving for retirement.
• Healthcare professionals have access to different retirement plans, such as 401(k), 403(b), and 457 plans, which offer tax advantages and employer matches.
• Tax efficiency is crucial in retirement planning, considering physicians' higher incomes.
• Balancing competing financial goals, such as paying off student loan debt and saving for children's education, requires personalized strategies.
• Starting early and investing money for growth are essential for successful retirement planning.

For more information contact Amy Walls and her staff at 503-610-6510 or click here Thimbleberry Financial.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Recently, the Oregeon DMV was hacked, compromising the drivers' licenses, photo, birth date, addresses, and last 4 social security digits of up to 3.5 million people.  In another example, an software employee stole 33,000 credit reports and sold them for $30 each, netting anywhere from $50-$100 million for scammers.

First, we explain how these hacks happen, through data breaches, your own online activity, and even just plain theft of your wallet or phone.  Amy shows us what these bad actors can do with your information.

Now, it's time to be your own super hero, by doing the following:

• Unmask the Invisitble Intruders - use AnnualCreditReport.com
• Ice Out The Enemy - by freezing or locking your credit (Amy explains the differences)
• Shield Your Secrets with Two Factor Armor - by enablying two-factor authentication (2FA)
• The Power of the Unbreakable Code - creating strong and unique passwords
• Dodge Digital Phantoms - identify and avoiding phishing scams.
• Fortify Your Digital Fortress - use only secure Wi-Fi networks, and make your own safe!

Through these strategies, you can fight "the never ending battle against cyber villains."

For more information contact Amy Walls and her staff at 503-610-6510 or click here Thimbleberry Financial.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Today they focus on three key areas: cash reserves, debt management, and cash flow. Healthcare workers often find it more stressful to manage their finances compared to the general population. Amy emphasizes the importance of having a cash reserve for emergencies and opportunities. She recommends having three to six months' worth of expenses set aside. Many healthcare professionals have lower cash reserves due to their higher incomes, but it is crucial to have a sufficient amount to cover unexpected expenses. Amy also highlights the significance of managing debt, including student loans, mortgages, and credit card debt. She suggests strategies such as paying off the highest interest debt first, or alternatively, using the snowball method. Additionally, Amy discusses the importance of cash flow and living within one's means. She explains that healthcare professionals often struggle with wealth accumulation due to factors such as the cost of education, late start in earning, and societal pressure to maintain a certain lifestyle. Amy encourages healthcare professionals to seek financial advice and education to better manage their finances.

**Key Takeaways:**

- Healthcare workers find it more stressful to manage their finances compared to the general population.

- Cash reserves are important for emergencies and opportunities. Aim for three to six months' worth of expenses.

- Healthcare professionals often have lower cash reserves due to their higher incomes, but it is crucial to have sufficient funds for unexpected expenses.

- Strategies for debt management include paying off the highest interest debt first or using the snowball method.

- Cash flow is about finding balance between current lifestyle and future goals. Seek financial advice and education to better manage finances.

For more information contact Amy Walls and her staff at 503-610-6510 or click here Thimbleberry Financial.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

For more information you can reach Amy and her staff at 503-610-6510 or email Thimbleberry Financial at https://thimbleberryfinancial.com/

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

And as always, she and her staff can be reached at 503-610-6510 or email Thimbleberry Financial at https://thimbleberryfinancial.com/

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

For more information contact Amy Walls and her staff at 503-610-6510 or click here Thimbleberry Financial.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Amy will answer a variety of questions like how much should one save for retirement and how to minimize tax liability while maximizing income and benefits. And she’ll discuss in some detail the importance of planning for retirement early on in your career.

Contact Amy and her team at  503-610-6510. Or at Thimbleberry Financial HERE.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

For more information reach out to Amy and her staff at 503-610-6510 or online at Thimbleberry Financial Services HERE!

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

For more information call (503) 610-6510 or reach out to Amy and her staff at Thimbleberry Financial  HERE. 

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Amy Walls has solid information to help you navigate this new higher interest rate environment. 

She also explains the phrase heard a lot these days: Marry the house; date the rate. Plus, Amy will discuss the ways in which people should be cautious about rates and prices.  

If you have questions about anything related to your financial future, reach out to Amy Walls and the team at Thimbleberry Financial at 503-610-6510  or click here: Thimbleberry Financial 

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

 If you have questions about anything related to your financial future, reach out to Amy Walls and the team at Thimbleberry Financial at 503-610-6510 or contact them at thimbleberryfinancial.com

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

What cash are we talking about? What cash could or should be structured?

Amy Walls will walk you through where, when and how to structure cash, and just as importantly, when not to.  

Thimbleberry Financial is focused on providing clients with the advice and tools needed to reach their financial goals. 

At Thimbleberry Financial we take the time to know our clients and their financial goals. 

We help our clients with all stages of their financial plan, from defining their goals to identifying possible strategies to implementing and reviewing the solutions.

Amy and her team are available for a more detailed discussion 503-610-6510 or visit here: Thimbleberry Financial  

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

What to do when you find yourself in this place?

She will explain the forms of stock where this could be an issue, advise on possible new strategies, and how to figure out which to choose. 

Finally, she will discuss a few other matters you may want to consider when dealing with company stock. 

For more info from Amy or her team contact them at Thimbleberry Financial  or call 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

In addition, Amy will talk about a few other significant changes, one in particular that will result in small businesses being incentivized to offer a 401(k).

If you have questions about anything related to your financial future, reach out to Amy Walls and the team at Thimbleberry Financial https://thimbleberryfinancial.com/  

Or give them a call at 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

In this episode new host Michelle O’Dell gets to know the how and the why she got into financial services in the first place. Most importantly, we learn her philosophies that shape financial planning that are tailored to each client’s requirements. Amy’s love for helping clients is why you want her on your side when it comes to making some of the biggest most impactful decisions of your life.

If you have questions about anything related to your financial future, reach out to Amy Walls and the team at Thimbleberry Financial https://thimbleberryfinancial.com/ 

Or call 503-610-6510 

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Two and a half years later, we find the opposite to be true.  As we emerge from the pandemic, clients have been distracted. We've lost sight of the simple things they enjoyed during lockdowns, and it's up to Amy and her team to help them reconnect with their passions.

The team at Thimbleberry Financial has changed through COVID, too.  They are now almost 100% virtual, with employees across the country.   This can be especially helpful for clients in the tech sector.   Amy walks us through how this new business model can better serve Thimbleberry's clients.

Want to learn more?  Contact Amy and her team at 503-610-6510, or visit them online at https://thimbleberryfinancial.com/

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

It's important to remember our last downturn (not counting the brief one in March of 2020) was way back in 2008. That means, for younger investors, they may not have ever seen a down market since they began investing.  Amy explains recency and primacy bias, and how to guard against each.

Today, we talk about specific strategies -and opportunities - in a down market.  These include lump sum investing vs dollar cost averaging, Roth conversions, and staying in the market.

Also, you should be evaluating your portfolio differently based on your age and proximity to retirement.  Amy explains.

Want to learn more?  Contact Amy and her team at 503-610-6510, or visit them online at https://thimbleberryfinancial.com/

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Significant moments, such as a New Year (or even a new month or week), can be used as an anchor point to set a goal. For example. did you know that statistically, you're more likely to finish a marathon at 40 than 39?  It's because "40" is a more significant anchor point.   This same idea can be applied to improving your diet, getting more exercise, or being more financially responsible.

More:  Daniel Pink's "When: The Secrets of Perfect Timing" https://www.amazon.com/When-Scientific-Secrets-Perfect-Timing/dp/0735210624

If you have questions about anything related to your financial future, reach out to Amy Walls and the team at Thimbleberry Financial at https://thimbleberryfinancial.com/

Or give them a call at 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

First, Amy explains the difference between a mutual fund and an index fund, with a clever fruit salad analogy.

Next, we walk through the differences between capital gains and capital losses, as well as short-term vs. long-term.  Investors don't control the trading inside a fund, so they have no control over what's a capital gain inside it.

We close with a business analogy to better explain the situation.

If you have questions about anything related to your financial future, reach out to Amy Walls and the team at Thimbleberry Financial at https://thimbleberryfinancial.com/

Or give them a call at 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Amy Walls of Thimbleberry Financial has been working with her clients to prioritize decisions - we don't want to make a mistake when it comes to our livelihood and our future!   Today, Amy and Jag discuss some strategies that can help give our brains a "breather" and combat decision fatigue.

Finally, we talk about which decisions should be the priorities when we look to our financial future.

If you have questions about anything related to your financial future, reach out to Amy Walls and the team at Thimbleberry Financial at https://thimbleberryfinancial.com/

Or give them a call at 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Amy starts with a story about a prescription SNAFU that led to today's topic.  In order to make a decision, you need as much information as possible.  What are your specifics with regard to spending and saving?  What are your priorities?  Do you have a cash reserve?

Amy and Jag explore some variables that may factor into your saving plans, including debts, housing situation and more.

And yes, the earlier the better. We break down the math of how expensive it can be to wait.

If you have questions about anything related to your financial future, reach out to Amy Walls and the team at Thimbleberry Financial at https://thimbleberryfinancial.com/

Or give them a call at 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

We focus on three categories:

• Mental Health
• Immediate Financial Needs
• To-Do List of Financial Items

If you have questions about what to do in this situation, or anything related to your financial future, reach out to Amy Walls and the team at Thimbleberry Financial at https://thimbleberryfinancial.com/

Or give them a call at 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

• What is an estate plan?
• Does an attorney need to be involved?
• What is a Trust and what does it do?
• How much should I expect to pay for setting this up?
• What documentation do I need?
• Once it's set up, is the work done?

If you have questions about estate planning, or anything related to your financial future, reach out to Amy Walls and the team at Thimbleberry Financial at https://thimbleberryfinancial.com/

Or give them a call at 503-610-6510.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

We talk about "Doom Squirreling" - when we are stressed out, we often find ourselves attracted to - and distracted by - countless other problems.   And there's no shortage of those causing emotional fatigue now, from the markets to recession talk, inflation, war, pandemic, politics and more.

Amy and Jag spend most of today's episode talking about ideas for dealing with emotional fatigue.  Find the ones that work best for you, including:

• Spending time with uplifting people
• Turning off the news
• Meditation
• Get out in nature
• Turn off the "noise" - social media and mobile notifications
• Finding a creative outlet
• Not being afraid to reach out to a trusted friend or mental health professional

Contact Amy and her team at Thimbleberry Financial online at https://thimbleberryfinancial.com/

Or give them a call at (503) 610-6510.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Unlike a password YOU come up with, these password managers generate their own secure, unique passwords.  A random series of letters, numbers, and symbols is much harder to hack than your pet's name!   Also, they often require multi-factor authentication, an added level of security.  You can choose which passwords to share with friends and family, and cut off access to a specific device if you lose that device.  And they often have an "Emergency Access" feature, where if something were to happen to you, you can designate a contact to have access to your information.

Amy and her team use a password manager for the extremely sensitive data they work with, and they encourage their clients to do the same.

For questions about  anything related to your financial future, reach Amy Walls and her team at Thimbleberry Financial at (503) 610-6510, or on the web at https://thimbleberryfinancial.com/

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

A recession is a "lagging indicator" - which means we can only tell if one exists in hindsight, not by looking ahead.  And if you knew a recession was coming, how much of your day-to-day life would you really change?  Remember, news outlets are always trying to get eyeballs and clicks - so take any hype you hear with a big grain of salt.

Yes, recessions can be scary and invoke many fears.  But in addition to media hype, this is because most Americans aren't financially prepared.   On average, a recession happens around every 5 years, and lasts 11 months.  That's means we only spend about 20% of our time in one!   

As always, it comes down to preparation.  Amy and Jag break down the best ways to prepare for a recession.  So when one comes, you'll be ready.

Want to know more?

Contact Amy and her team at Thimbleberry Financial online at https://thimbleberryfinancial.com/

Or give them a call at (503) 610-6510.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

As a property owner, you have an exemption on the gain in basis between your purchase and your sale of a property.  That's $250,000 for single and $500,000 for joint.  Here's an example for a single person.  If you bought a home for $344,000 but sold i for $565,000, that's a gain of $221,000.  That's within the $250k limit- no tax implications.

This math can be complicated by other scenarios, including:

• Staying in your home longer than expected
• DIY improvements vs. using a contractor vs. somewhere in between
• Passing of a spouse (you have two years from date of death to use the joint $500k exemption)

Amy and Jag cover what the IRS defines as capital improvements to a home (that would change the basis) and dive into another specific example.

For a married couple, a home is purchased by a married couple for $650,000 and sold for $1,300,000.

• Without tracking the change in basis, that's a gain of $650,000, over the limit of $500k. The remaining $150k would be subject to capital gains taxes.
• If they did $220,000 of improvements to the house, the original $650k basis is now $870k.  The $1.3 million sale price is only $430k in gains, within the exemption, no capital gains taxes due.

It's important to track any and all capital improvements to your home.  And track them with your taxes every year, so you're not scrambling to find  years - or decades - worth of records when you're ready to sell your property.  

For questions about  anything related to your financial future, reach Amy Walls and her team at Thimbleberry Financial at (503) 610-6510, or on the web at https://thimbleberryfinancial.com/

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

1. Is it really possible to create your own sabbatical? 
2. What should be considered in deciding to create your own sabbaticals?
3.  What does the financial impact of a sabbatical look like?
4. If you take a sabbatical, how do you explain a 6 month breaks in your employment history?

For questions about  anything related to your financial future, reach Amy Walls and her team at Thimbleberry Financial at (503) 610-6510, or on the web at https://thimbleberryfinancial.com/

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Are these questions for the retirement years, or for earlier?

How do you define aging and the parameters of the discussion?

What do I need to know to talk about this with my spouse/partner?

Once you sort through these ideas, what's next?

What resources are available to folks struggling with these conversations?

For questions about  anything related to your financial future, reach Amy Walls and her team at Thimbleberry Financial at (503) 610-6510, or on the web at https://thimbleberryfinancial.com/

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

It's no secret that Americans spend much more time planning out our vacations than our retirement.  But you can take aspects of your vacation and see if it has long-term appeal for you in the longest vacation of your life - retirement.   For example, Amy's not a fan of Florida's alligators, but there's appeal in living in a place with no state income tax.

There are other more practical considerations too.  Do you want to live in a 55+ community with other retirees? Do you want to live near the ocean? Would a lake suffice? Amy and Jag break down some of the variables you cant think about while on vacation.

For questions about  anything related to your financial future, reach Amy Walls and her team at Thimbleberry Financial at (503) 610-6510, or on the web at https://thimbleberryfinancial.com/

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

For many, life insurance can be complicated.  We break it all down for you today, starting with temporary (term) insurance and permanent life insurance - and the different categories within it.

As with most types of insurance, we'll have needs at different points in our lives, depending on income, assets, and what needs to be protected.

Within permanent types of insurance, Amy explains the differences between Whole Life Insurance, Universal Life Insurance, and Variable Universal Life Insurance policies.  They can all be great tools, but very dangerous if used improperly.

Remember, a life insurance policy isn't about taking care of yourself.  It's about taking care of those you care about.

Finally, Jag asks Amy about those who may not need life insurance.

For questions about  anything related to your financial future, reach Amy Walls and her team at Thimbleberry Financial at (503) 610-6510, or on the web at https://thimbleberryfinancial.com/

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Today, we wanted to take a moment to introduce the Thimbleberry Financial team, and how they will work with you to manage your money.

Amy and her team focus on six core values.  She explains what each means and translates to.

1. Integrity
2. Personal
3. Predictable
4. Simplicity
5. Focused
6. Control

While not intentionally created this way, the Thimbleberry team is all female.  It starts with Amy as the advisor (although we will have a second taking her CFP exam soon).  As the firm grows, we will develop service teams to deal with clients in specific sectors, including a paraplanner, operations specialist, and of course our office manager. This will enable us to super-serve our clients, while not overwhelming them with too many people to talk to.   We meet almost all our clients virtually and that will likely continue. 

As a CFP (Certified Financial Planner), Amy also is held to a fiduciary standard and must act in the best interest of her clients.  She clears up some confusion around this term and explains what it means for you.

Finally, Jag asks a question that's been on his mind for the last 30 months.  Where did the name Thimbleberry Financial come from?  You'll like Amy's answer.

For questions about  anything related to your financial future, reach Amy Walls and her team at Thimbleberry Financial at (503) 610-6510, or on the web at https://thimbleberryfinancial.com/

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

First, we look at the tax triangle - and the three "corners" of assets, based on tax status.  Next Amy explains the  5 ways to contribute to a Roth account:

• Direct contributions
• Employer sponsored Roth plans (401k, 403b, and 457 plans)
• Converting Pre-Tax money to a Roth IRA
• Converting After-Tax money to a Roth IRA (back door Roth)
• Converting After-tax 401k money to Roth 401k (Mega back-door Roth)

Amy explains which of these strategies are could to be protected, which could change, and which could be eliminated altogether. If these changes happen, what options will we have available?  Finally, Amy explains why she's advising to hold off on Roth conversions at present.

For questions about  anything related to your financial future, reach Amy Walls and her team at Thimbleberry Financial at (503) 610-6510, or on the web at https://thimbleberryfinancial.com/

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Previously. Amy's daughter hasn't been concerned with money. She's always enjoyed artistic pursuits, but a recent interest in quilting had her needing supplies.  So Amy started breaking down what investing could look like, if her daughter got a part time job and saved money in addition to spending money.  Wait until you hear these numbers!

Now, it's not always the right time to save and invest.  This of course depends on your individual situation and time horizon. 

For questions about  anything related to your financial future, reach Amy Walls and her team at Thimbleberry Financial at (503) 610-6510, or on the web at https://thimbleberryfinancial.com/

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

We look at the criteria involved for you to actually worry about something, and how much of that applies here, depending on your individual situation. 

Next, Amy talks about what the war in Ukraine could mean for the future of the market. And while we don't have a crystal ball, Amy provides some historical data that can inform opinions and predictions.  This includes what the market did after Pearl Harbor and 9/11.

Before you worry, know your status - be sure to have a clear picture of your financial situation. And if you don't know, find out!

Differentiate between what you can control and what you can't.  And please avoid "market-tainment" shows - designed to play on your emotions.

Finally, there may be opportunities here, from rebalancing, to Roth conversions, to defense and energy stocks.

For questions about any of this, or anything related to your financial future, reach Amy Walls and her team at Thimbleberry Financial at (503) 610-6510, or on the web at https://thimbleberryfinancial.com/

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Amy doesn't want to manage budgets for her clients. She wants to create spending plans. The difference? Mindfulness. To borrow a page from Marie Kondo, spending should be focused around what creates joy.

In a previous episode, we discussed the Aesop's Fable about the ant and the grasshopper.  Ants are savers, and grasshoppers are spenders.  Which are you?  Amy discusses mindful strategies for both sets of personalities. And Jag shares a story about how he (the grasshopper) and his wife (the ant) have found ways to help each other and compromise.  And Amy shares some additional tips as well.

Finally, mindfulness can expand into your investing - we look at socially responsible investing, ESG investing, and impact investing.

For questions about mindfulness and money, or anything related to your financial future, reach Amy Walls and her team at Thimbleberry Financial at (503) 610-6510, or on the web at https://thimbleberryfinancial.com/

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

When does paying off your mortgage help with a successful retirement? 

When can it hurt your retirement?

When does it make sense to pay off a mortgage?

What variable should be considered when thinking about paying off a mortgage?

Finally, what about paying off the mortgage early?

For more information on how this affects your individual financial situation, or anything related to your financial future, reach out to Amy Walls and her team at Thimbleberry Financial.

https://thimbleberryfinancial.com/

(503) 610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

https://thimbleberryfinancial.com/

(503) 610-6510

Many folks in the tech world can receive "tender offers" - a proposition to buy shares of your company holdings. This could come from the company or an outside party.  What do you do when you receive a tender offer?

Today, Amy Walls of Thimbleberry Financial explains why tender offers are made, and what factors you should consider when evaluating whether you should sell, and if so, how much you should sell.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

https://thimbleberryfinancial.com/

(503) 610-6510

Amy Walls and the team at Thimbleberry Financial work with many clients in the tech sector.  When an employee lands their first high-salary job in this field, it can be overwhelming. Today we talk about what to do.

What is the first thing someone to do? Maintain the Status Quo - temporarily.

• What’s next? Look at all of the offered benefits and make choices to set yourself up for success
• Insurance
• 401k
• Employee Stock Purchase Programs
• Equity Compensation (RSU's, Stock Options)
• Outside items, like umbrella insurance and estate planning
• Is a Mega Back-Door Roth an Option?
• Look ahead to future needs
• Aging out – Conservatively, how much time do you have?

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

https://thimbleberryfinancial.com/

(503) 610-6510

The behavior and psychology of personal finance is something that Amy Walls is always studying at Thimbleberry Financial.  In our first podcast of 2022, we are discussing the concept of "Your Future Self."

Your future self is just that - you in the future. You can make decisions today, that, if you keep your future self in mind, will benefit you down the road.   This might mean having to fight through "present bias" or what others think your future self should be.

It's important to exercise grace and empathy.  You won't always make the right decisions, but allow yourself to learn from your mistakes.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

https://thimbleberryfinancial.com/

(503) 610-6510

An Annual Financial Review can be a great tool to evaluate your 360 degree financial future.  Often, this is the time of year when we take stock and think about these things.   Today, Amy and Jag go over the elements of an annual financial review and how to get started.

• What is an Annual Financial Review?
• What should be looked at in an Annual Financial Review?
  • accounts
  • cash allocations
  • cash flow
  • changes (income, taxes, benefites, expenses)
• What types of questions should I be asking my advisor, and is there anything I shouldn't ask him or her?

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

https://thimbleberryfinancial.com/

(503) 610-6510

Today, Amy Walls from Thimbleberry Financial walks us through the top 6 retirement planning mistakes. They are:

• Not thinking about how they will spend their time in retirement
• Lack of Diversification
• Lack of Rebalancing
• Learning Not All Savings Are Equal
• Cashing Out a Retirement Plan
• Not Planning for  Health Care Costs

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

https://thimbleberryfinancial.com/

(503) 610-6510

"Shrinking your income" may not seem like a good idea, but it's actually a psychological trick to increase your savings. Today, Amy Walls from Thimbleberry Financial explains the process.

If you think you have less to spend, it will change your habits and decisions. Automatically take different categories of expenses "off the top," such as:

• Fixed Expenses
• Non-Monthly Expenses (travel, gifts, savings, etc)
• Spending/Discretionary Money
• A family-specific category, like child-related costs

By taking all of these items off the top, it appears you have less money to spend, and guess what? You'll spend less.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

https://thimbleberryfinancial.com/

(503) 610-6510

Qualified Charitable Distributions, or QCD's, are an effective way to lower your tax burden while contributing money to a cause important to you.  Today, Amy Walls of Thimbleberry Financial walks us through all things QCD, including:

• What is a Qualified Charitable Distribution?
• What is the benefit of making a Qualified Charitable Distribution?
• Who is eligible?
• What are instances where people should consider doing this?
• What rules does someone need to be aware of?

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

https://thimbleberryfinancial.com/

(503) 610-6510

The tax plan being debated in the US House of Representatives can have significant impacts on the financial futures and retirements of many Americans.  Today, Amy Walls of Thimbleberry Financial highlights some key areas of the legislation, as of our recording date of October 12th.

• What are some differences between the House plan and President's Biden's plan?
• Who stands to be most impacted by these new laws?
• What are some changes that could impact high earners and high net worth individuals?
  • Tax brackets and capital gains
  • Roth Conversions
• What are some changes that could impact everyone?
  • Could Back-Door and Mega Back-Door Roth Conversions go away?
  • Wash Sale Rules extended to cryptocurrency
  • Child and Dependent Care Credits
• What isn't in the plan?
  • No elimination of step-up in basis
  • Nothing with social security
  • SALT (State and Local Tax) Deductions

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

If you find yourself on the receiving end of a stock tender offer, there are a number of factors that should go into your decision. Today, Amy Walls of Thimbleberry Financial breaks them down.

• What is your purpose for the money?
• Are your short or long term goals more of a priority?
• Understand if there is a particular type of stock (RSU, ISO, etc.) that the offer applies to.
• What are your tax implications for accepting the offer?
• ....and more!

At Thimbleberry Financial, Amy Walls and her team make it a priority to really get to know their clients and what's important to them. This goes far beyond their investments.  If you'd like to contact the team and set up an appointment, you can visit:

https://thimbleberryfinancial.com/

or call: 503-610-6510.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

You need to take stock of both your financial situation and your priorities.  They aren't one and the same!

Financially:

• Knowing your accounts, who has access to them, and how to connect the people to each other
• Estate Planning - wills and trusts, financial and health care powers of attorney, and beneficiary designations - are you happy with where things are set?
• Other items like joint accounts, gifting of assets, and accelerated riders on life insurance

Priorities:

• Your Bucket List
• Maybe more importantly, the quieter priorities - for example, anything you want to leave behind for loved ones, like notes and videos
• Who you want to spend time with - or even reconcile with
• Making arrangements for your own funeral or service if you so choose.

At Thimbleberry Financial, Amy Walls and her team make it a priority to really get to know their clients and what's important to them. This goes far beyond their investments.  If you'd like to contact the team and set up an appointment, you can visit:

https://thimbleberryfinancial.com/

or call: 503-610-6510.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

1. Spending
2. Savings rate
3. Retirement date
4. Inflation rate
5. Investment returns
6. Fixed Income Streams and their growth rate, if any
7. Life expectancy
8. Where your money is saved and your tax bill 

We also talk about retirement not being a "switch" you flip.  Once you stop working, that doesn't mean you stop planning!

Contact:

Thimbleberry Financial Website: https://thimbleberryfinancial.com/

Or call: 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Today, Amy Walls of Thimbleberry Financial walks through strategies for inconsistent income earners, including:

• Increasing cash reserves
• Working with a CPA
• Asset allocation
• Making a plan
• Adjusting banking strategies

Contact:

Thimbleberry Financial Website: https://thimbleberryfinancial.com/

Or call: 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Today, Amy Walls of Thimbleberry Financial explains the unique, mutually responsible relationship she maintains with her clients, and what happens when this dynamic works well - a tandem of strategy and wealth management.  Thimbleberry and clients both have action items after every meeting.

Sometimes, this approach isn't the right fit.  Clients may become unresponsive, or they may decide this isn't the right type of relationship for them.  In these cases, Amy explains how both parties can exit the relationship.

Contact:

Thimbleberry Financial Website: https://thimbleberryfinancial.com/

Or call: 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

1. Notice the Positive
2. See Opportunity
3. Control and Accept
4. Focus on Solutions
5. Take Purposeful Action
6. Reach Out

Contact:

Thimbleberry Financial Website: https://thimbleberryfinancial.com/

Or call: 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

The Income Danger Zone is when you're earning enough to not be living paycheck to paycheck, but you aren't to the point where you can live without a budget.  And it happens to many of us, often when growing in a career or when childcare expenses lessen. 

You may be in the Income Danger Zone if you find yourself splurging, and promising to make it up next month, the proverbial "robbing Peter to pay Paul."  Also, inconsistent income can easily lead to the Income Danger Zone.

This Income Danger Zone can lead to "lifestyle creep," as well as debt, and even emotional and behavioral pain.  The keys to avoiding it are intentionality and planning.

Contact:

Thimbleberry Financial Website: https://thimbleberryfinancial.com/

Or call: 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

How do you make these conversations easier?

• Have a scheduled conversation in a neural place.
• Think about your "why" beforehand.
• When meeting, find common ground, acknowledge mistakes, and listen!

What questions can you ask to start the conversation?

What actions can you take as a couple to align spending?

Contact:

Thimbleberry Financial Website: https://thimbleberryfinancial.com/

Or call: 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Today, Amy Walls of Thimbleberry Financial walks us through tax-efficient investing, or minimizing the amount of taxes you owe.

There can be a difference in taxes on long term vs short term capital gains.

Rate of return after taxes and fees is what's important.

Taxes on investments are often paid out of cash flow, not out of those investments themselves!

Amy explains stock, mutual fund, ETF, and muni bond investments, but also warns of pitfalls, including surprise tax bills, rebalancing, and emotions/bias.

For help with your financial future, contact Amy Walls at Thimbleberry Financial:

https://thimbleberryfinancial.com/

Or call: 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

1. Taxes on stock and Equity Comp
2. Taxes on investments for the longterm
3. 4% Rule
4. Sequence of Return Risk
5. Biases

For help planning for your company's IPO, or for any assistance with your financial future, contact Amy Walls at Thimbleberry Financial:

https://thimbleberryfinancial.com/

Or call: 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

While the priority of needs may sometimes vary, you need to start with a foundation. 

1. Cash Reserves
2. Debt
3. Protection
   • Life Insurance
   • Disability Insurance

Once you have the foundation in place, you can focus more on medium and long term goals, the walls, or "floors" of your house. These could be college funds, vacation homes, or other goals.  

Next, you can focus on retirement and financial independence. 

Finally, at the top, you can take care of estate planning.

And don't forget the cloud above your house or pyramid - taxes.  Amy explains.

For help with your financial future, contact Amy Walls at Thimbleberry Financial:

https://thimbleberryfinancial.com/

Or call: 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Amy explains what differs these plans from qualified plans like 401k and 403b plans.   Employees can often contribute more money. By not being in the employees name, taxes are not paid at the time of compensation, but there are risks to these plans.

Amy explains the pros and cons, and can help you decide if one of these plans is right for your individual situation.

For help with your financial future, contact Amy Walls at Thimbleberry Financial:

https://thimbleberryfinancial.com/

Or call: 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

70 percent of people who come into sudden money deplete those funds within a few years, so today Amy walks us through steps to avoid windfall pitfalls.

• Plan ahead
• Be honest, not manipulative
• Put a strong team in place
• Make a wish list
• Keep quiet!
• Save appropriately
• Take responsibility for mistakes.

For help with your financial future, contact Amy Walls at Thimbleberry Financial:

https://thimbleberryfinancial.com/

Or call: 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

• This includes:
• Responding to communication.
• Revisiting the planning process annually
• Updating the plan
• Knowing what's important to our clients, but also where the boundaries are
• Knowing which clients are a good fit, and which ones are not
• Providing education
• Having processes and setting expectations around them
• Honest communication, even when it's what a client doesn't want to hear.

As an example, Amy began scheduling her clients out for the year. She explains how well that was received.

Resources:

Thimbleberry Financial Website: https://thimbleberryfinancial.com/

Thimbleberry Financial Phone Number: 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

When investors believe a stock is about to fall, they can bet against it by "shorting" it - they profit when the value falls.  But they also lose when the value rises.  Tough times for a brick-and-mortar video game retailer had been well documented and Wall Street assumed the stock price would fall.   Then the investors on Reddit jumped in, buying up the stock so quickly it shot the share price from $18 to $347, costing hedge funds $5 billion by some estimates.

The Robin Hood app temporarily stopped day traders from  buying up the stock, not because of collusion with Wall Street, but to meet their financial obligations as an RIA. 

The bottom line - investing in short-term fads or trends is dangerous.  Retirement planning should be a slow, long-term cautious approach that won't be affected by momentary market swings.

Resources:

Thimbleberry Financial Website: https://thimbleberryfinancial.com/

Thimbleberry Financial Phone Number: 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

What are the different loan types?

• Primary
• Fixed Second or Second
• HELOC

What happens to my 2nd or HELOC if I refinance my primary loan?

When does it make sense to refinance?

What is the process to refinance?

Can someone else (my advisor) handle this for me? (Spoiler alert: No!)

What if my house is paid off -what are my choices?
 

Resources:

Thimbleberry Financial Website: https://thimbleberryfinancial.com/

Thimbleberry Financial Phone Number: 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

1. Shore-up or Build a cash reserve
2. Have a plan for student loan debt and know the consequences of that plan
3. Obtain disability and life insurance policies.
4. Start saving for retirement/know how much you need to save
5. Start working on other financial goals.

Doctors are notoriously bad at saving and financial planning.  Like patients who find them, docs should seek out an expert to help.

Resources:

Thimbleberry Financial Website: https://thimbleberryfinancial.com/

Thimbleberry Financial Phone Number: 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

1. What does “going public” mean? And what does it mean to me?

2. What do I need to know and do? What do I need to know about stocks and lock up periods?

3. What do I do with my stock? What are RSUs and ISOs?

4. Are you financially independent? How does this play into the decision process?

5.  Special Tips - don't increase spending and have a plan.

• Pay down Debt
• Buy or upgrade Home – know your means
• Fund College for kids
• Front-load retirement/Buy yourself future flexibility

6, What about diversification and different types of investments

Each situation is different based on goals, expenses/spend down rate, retirement age, health and life expectancy.

Resources:

Thimbleberry Financial Website: https://thimbleberryfinancial.com/

Thimbleberry Financial Phone Number: 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

First we recap the ways we can contribute to a Roth IRA. They are:

• Contributions – annual contribution put directly into a Roth IRA. Directly is the key word here. 
• Conversions – This is money put into a traditional IRA, or 401(k) or 403(b) and then converted into a Roth. There are two types:
  • Pre-tax: an employer plan that is rolled over into a Traditional IRA or Rollover IRA that is later CONVERTED to a Roth IRA.
  • Non-Taxable Conversion: This is the strategy we’ve talked about before that is often referred to as a Back-Door Roth. Contributions are made after-tax to an IRA, and then CONVERTED to a Roth IRA.
• Rollover of a designated Roth account – This is when your employer allows you to
• Contribute after-tax money to your 401k or 403b as a Roth designated contribution. Not all employers do this.
• Earnings: This is growth on the money inside the account.

Now we can look at the ways in which money is distributed out of a Roth account, keeping in mind the acronym  "Real Tacos Can Not Contain Eggplant."

Assets are distributed in the following order:

1. Regular Roth IRA participant contributions, includes rollovers of directly contributed Roth 401(k) and 403b dollars.

2.Taxable Conversion and rollover amounts- Pre-tax IRA contributions or an old employer plan that is converted.

3.Non-taxable Conversion and rollover amounts - After-tax IRA contributions and internal 401k conversions (Mega backdoor Roth)

4.Earning on Roth assets- Growth.

For illustrative purposes, Amy gives an example of these. Here it is, laid out.

Sara opened a Roth IRA in March 2019 and makes contributions for 2018 and 2019. The 2018 contribution treats the account as if it were opened on January 1, 2018. In 2019 she converted a $35,000 Traditional IRA to a Roth IRA. Sara is 57 years old at the end of 2020. The account contains:

• $15,000 in contributions for 2018, 2019, and 2020.
• $30,000 taxable traditional IRA coversions from 2019.
• $5000 of non-taxable Roth IRA conversions from 2019.
• $5000 in earnings.
• $55,000 TOTAL

Let’s say Sara wants to take a $52,000 distribution.

• Sara can take up to $15,000 without taxes and penalties.
• The next $30,000 that is from taxable traditional IRA conversions will not be subject to income tax, but will be subject to the 10% penalty. This is because she paid tax on the conversion.
• The next $5000 of non-taxable Roth conversions are not subject to taxes or penalties as the conversion was a non-taxable event.
• The last $2000 is from earnings will be subject to income tax and early distribution penalty of 10%. The penalties and taxes are because she is tot 59.5 and the account has not been open 5 years.

The rules around Roth accounts are not always easy to understand.  Hiring a professional like Amy can go a long way.  You can find her online at https://thimbleberryfinancial.com

or give her a call at 503-610-6510.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

• Specific
• Measurable
• Attainable
• Relevant
• Time Bound

SMART Goals also need to resonate with you - if you don't have a connection to the goal, you won't achieve it.

SMART Goals should also be put into writing - and there's neuroscience to back this up!  Amy gives us a high level recap of Mark Murphy's study "The Gender Gap and Goal-Setting" (link below).

People who have vividly written down their goals are 1.2 to 1.4 times more likely to accomplish their goals. Writing things down happens on two levels: external storage and encoding. It doesn’t take a neuroscientist to know you will remember something much better if you’re staring at a visual cue (aka reminder) every single day.  And writing improves the encoding process. 

Finally, there needs to accountability.  It's much easier to achieve a goal if you have someone to hold you accountability.  That's where a financial advisor like Amy can help!

Resources:

Mark Murphy Study in Forbes:

https://www.forbes.com/sites/markmurphy/2018/04/15/neuroscience-explains-why-you-need-to-write-down-your-goals-if-you-actually-want-to-achieve-them/?sh=7415a20a7905

Thimbleberry Financial Website: https://thimbleberryfinancial.com/

Call Thimbleberry Financial: 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Here are 4 steps to making good decisions in stressful circumstance.

1. Take space and Identify what’s important to you.
2. Recognize and acknowledge what you don’t control and influence. Then move past.
3. Focus on where you do have power...the things you control and influence.
4. Reduce your decisions.

We break each of these steps down, including an example of how a significant change in Amy's daughter's virtual learning affected her, and how they dealt with it as a family.

All of these ideas are key when dealing with money.   Stress can cause you to make poor financial decisions, and that's why its important to work with a trusted professional on your finances.

Contact:

Thimbleberry Financial Website: https://thimbleberryfinancial.com/

Call or text Thimbleberry Financial at 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Yes, some people will see tax increases, but this is mainly for those making over $400,000 per year. 

Biden-Harris Tax proposals include:

• $8000 credit for childcare
• A tax exclusion for student loans that are forgiven. Currently, there are a few exceptions, but most forgiven student loans are taxed as income to the borrower.
• A refundable tax-credit for low to middle income households that contribute to IRA’s and 401K’s.
• A $5000 credit for family caregivers, and a catch-up contribution for those caregivers to add money to their IRA or 401K that they may have missed.

We also take a historical look at how the market has done in Republican vs Democratic Presidents, a split Congress, and how Donald Trump's stock market fared, historically.

Finally, Amy explains what you should - and shouldn't - do, both in the current lame duck period, and at the beginning of the next administration.

More information:

Business Insider article on Democratic Presidents: https://markets.businessinsider.com/news/stocks/stock-market-election-democratic-republican-presidents-better-performance-economy-gdp-2020-8-1029528932

Forbes article on S&P returns under different Presidents: https://www.forbes.com/sites/sergeiklebnikov/2020/07/23/historical-stock-market-returns-under-every-us-president/?sh=1ddc089faaf4

Fortune article on markets under a divided Congress: https://fortune.com/2020/11/04/stock-market-2020-election-results-divided-congress-house-senate-democrats-republicans-us-economy/

Thimbleberry Financial Website: https://thimbleberryfinancial.com/

Call or text Thimbleberry Financial at 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

1. Should I hold onto the stock?
2. I know what’s going on in my company. Our stock is going to go sky-high. I’d be crazy to sell it.
3. Why should I sell my stock if it’s doing well?
4. When I log into my account, it says I have lots more than you say I do. Why?
5. Shouldn’t I always put as much as I can in my ESPP if I get a discount?

More information:

Thimbleberry Financial Website: https://thimbleberryfinancial.com/

Call or text Thimbleberry Financial at 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

As of the last census, nurses were 91% women (though we expect that to change with this year's count). Statistically, women are more likely to live longer, and tend to be more natural caregivers.

Amy explains why retirement is not a light switch, or an Instant pot - it needs to be carefully planned out , using money as a tool.

We also cover why nurses , caregivers that they are, sometimes have other family members to take care of, and how that can have an impact on their plans.

Finally, we look at nurses' ability to modify their schedules, and wind down toward retirement.  We explore why some nurses are happier in this phase than their retirement itself.

Bottom line, nurses are amazing people with a unique demeanor and skillset for taking care of others. They shouldn't be afraid to seek specialized help for themselves -with a financial advisor.

More information:

Thimbleberry Financial Website: https://thimbleberryfinancial.com/

Call or text Thimbleberry Financial at 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

• Maintain your cash reserve
• Have a long-term plan for your investments, and don't be scared by short-term market volatility
• Focus on what you can control
• Prepare for Possible Opportunities if there IS a market drop.
• Talk to an advisor.

More information:

Thimbleberry Financial Website: https://thimbleberryfinancial.com/

Call or text Thimbleberry Financial at 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

We define net worth and depreciation.

We examine the inconsistencies between what Trump has claimed and what the tax documents show.

We explain the debt that President Trump has coming due, and what the concerns are around a possible second term.

More information:

Investopedia definition for Net Worth: https://www.investopedia.com/terms/n/networth.asp

Investopedia definition for Depreciation: https://www.investopedia.com/terms/d/depreciation.asp

Just Security's 10 Takeaways from the Trump Tax story: https://www.justsecurity.org/72604/ten-quick-takeaways-from-the-new-york-times-bombshell-article-on-trumps-tax-returns/?fbclid=IwAR1SAf8REsKT8piX8CYxNwPxWaWkwSVCOrrLy80-rr9ne3wkkOrHF0lVfZs

Thimbleberry Financial Website: https://thimbleberryfinancial.com/

Call or text Thimbleberry Financial at 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Brent specializes in personal growth, a topic we often discuss on this show.  Personal growth is important in all areas of life, but also when it comes to your finances.

Brent goes on to explain the challenges of personal growth, beginning with taking your own worldview and biases, and "throwing them out the window." This can be even more challenging in the world of multi-person video conferences and social media.

Learning is not child's play. We cannot learn without pain. - Aristotle.

It's important to create a safe space for people to feel comfortable to learn, and this is best done in person.  

Amy and Brent discuss the book "The Culture Code" by French psychologist Clotaire Rapaille  - and how our experiences shape our worldviews. The older we get, the more challenging it can be to change them.  This applies to everything from personal finance to politics.

Finally, Brent explains the concepts of agile working and retrospective, and how they go together in the workplace, especially in the tech sector.

Mentioned in this podcast:

The Culture Code by Clotaire Rapaille

Project Retrospectives by Norman Kerth

Agile Retrospectives by Esther Derby and Diana Larsen

More information:

Thimbleberry Financial Website: https://thimbleberryfinancial.com/

Call or text Thimbleberry Financial at 503-610-6510

Email Brent: Brent@foliosus.com

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

While we can't speak for all women, many are influenced by things like value set, balancing responsibilities inside and outside the home, and a wage gap that is still very real.

Married women often take a back seat in the financial planning process, even though, statistically, they outlive their husbands!  Amy discusses how she works with women to make sure they are actively participating in their financial goals.  There are 4 main points.

• Identify what's important financially
• Provide education around women's financial issues
• Create a solid path forward
• Permission to say yes - and to say no

More information:

Thimbleberry Financial Website: https://thimbleberryfinancial.com/

Call or text Thimbleberry Financial at 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Many people need to cut their spending, but for some clients, Amy actually recommends an increase in spending.  This involves letting go of the guilt that sometimes comes with spending money. She explains.

There are also "rules of thumbs" for percentages of how much of your paycheck you should save, what should go to expenses, and what you can spend.  And the numbers change with bonuses.

Finally Amy shares some spending tips about credit cards, budgets for variable expenses, grocery shopping and intentional spending.

More: 

Thimbleberry Financial Website: https://thimbleberryfinancial.com/

Call or text Thimbleberry at 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

A Financial Planning First advisor starts with planning and a general understanding of your financial situation, before worrying about your investments.  In the first meeting with Shanna or Amy, you may be asked questions you weren't expecting, in order for your advisor to gain a 360 degree understanding of your world.

A Financial Planning agreement very specifically outlines the responsibility of the client to keep information updated, so that the advisor can keep the plan updated.

There's a common misconception that advisors are either commission based or fee based.  Amy and Shanna are both hybrid advisors, enabling them to offer their clients a wider array of services and products to meet their individual needs.

Shanna's Contact Info:

Website: https://www.heritagefinancialaz.com/

Call Heritage Financial at: (480) 397-1184

Amy's Contact Info:

Website: https://thimbleberryfinancial.com/

Email: info@thimbleberryfinancial.com

Call Thimbleberry Financial at: 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

They became fast friends, despite a hiccup at the beginning of the relationship that they explain.

First, Amy and Shanna were tasked with creating a "Disaster Recovery Plan" - what to do in the event of a natural disaster.  It ended up being fortunate that they were in different states, to back each other up if one office went offline.

Beyond that, Amy and Shanna created a "Continuity Plan," to work for each other's clients in the event something happened to one of them.  This meant having a shared set of values and approaches to dealing with their clients.

Amy's Contact Info:

Website: https://thimbleberryfinancial.com/

Email: info@thimbleberryfinancial.com

Call: 503-610-6510

Shanna's Contact Info:

Website: https://www.heritagefinancialaz.com/

Call Heritage Financial at: (480) 397-1184

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

1. They start their careers late after lots of school and potential debt.
2. Their incomes tend to be high.
3. Their work is often quite specialized.
4. There can be pitfalls and opportunities around retirement savings
5. They are used to giving advice. Seeking advice can be foreign and uncomfortable.

Amy explains each one of these items and why they can be troublesome.

Resource: The Millionaire Next Door: https://www.amazon.com/Millionaire-Next-Door-Surprising-Americas/dp/1589795474

Contact info:

Website: https://thimbleberryfinancial.com/

Email: info@thimbleberryfinancial.com

Call Thimbleberry Financial at: 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Contact Amy at Thimbleberry Financial:

Website: https://thimbleberryfinancial.com/

Email: info@thimbleberryfinancial.com

Call Thimbleberry Financial at: 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

It's important to lead by example, be intentional, and teach kids about money.  Those little sponges often pick up on more than we realize.  It's also OK to let them fail.  Failure can be a great teacher, and it's better to learn by losing $5 now than $500 later.

We also discuss the idea of allowances.  It needs to set up and align with your desired outcomes, and it can be part of a good framework. It allows kids to be part of a community, have a job and job description, and even earn bonuses.

You can also teach your kids about short, medium, and long terms savings - even introducing concepts like compound interest and delayed gratification. Amy explains how you can easily do this.

Finally we look at teaching spending habits.

Amy's Blog Post on having the money conversation with your kids: https://thimbleberryfinancial.com/money-conversation-with-your-kids/

Resource: Money Doesn't Grow on Trees Book

Contact:

Email: info@thimbleberryfinancial.com

Call: 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

We need to be prepared for the possibilities of:

• Reduced income due to job loss or illness
• Loss of life
• Potential end of life expenses, such as funerals and more

With regard to job loss - whether it's happened to you or you fear it might:

• Have a cash reserve
• Manage your debt
• What liabilities do you have?
• Don't do anything rash!

Preparing for the unthinkable - making arrangements for end of life is about making the process easier on your loved ones, including:

• Estate planning
• Life insurance
• Access to online accounts (passwords)
• Funeral arrangements
• Final Wishes
• Beneficiaries

We close with some of the "silver linings" of COVID-19, and the perspective and ideas the pandemic is providing to many clients and families.

Want more info on  the end of life planning process?   Email info@thimbleberryfinancial.com

To make an appointment with Amy:

www.thimbleberryfinancial.com

Or cal 503-610-6510.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Finally, we look at how the world may be different when we come out of this, and Amy explains how she is now working with clients remotely.

Thimbleberry Financial Website

Email Thimbleberry Financial

Call Thimbleberry Financial at 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

• Stimulus Checks
• Tax Deadlines
• Investment Rule changes, including Required Minimum Distributions
• Student Loans
• Charitable Donations
• Healthcare Costs

Thimbleberry Financial Website

Email Thimbleberry Financial

Call Thimbleberry Financial at 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

• Why is this important?
• We don’t know what we don’t know.
• It’s easy to think we are looking at all of the information. And being open-minded to it.
• It’s human nature to have an opinion.
• Recognizing biases and then finding the truth allows for a better assessment of the situation.

There are many biases in investing, and today we will cover just a few, including confirmation bias, loss aversion bias, mental accounting, and illusion of self control.

Thimbleberry Financial Website

Email Thimbleberry Financial

• Call Thimbleberry Financial at 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Thimbleberry Financial Website

Email Thimbleberry Financial

• Call Thimbleberry Financial at 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

• Not being aware of income limits
• Thinking a Roth conversion can be undone
• Thinking a Roth IRA is the same as a Roth 401k/403b/457
• RMD and other distribution rules

In today's episode, Amy and Jon delve into these common misconceptions that can often lead to expensive mistakes.

Thimbleberry Financial Website

Email Thimbleberry Financial

• Call Thimbleberry Financial at 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

• How do you work and what's your focus?
• Are you a CFP (Certified Financial Planner)?
• Who do you typically work with?
• How many clients do you serve?
• How are you paid?
• Do you have a succession plan?
• Who supervises you?

In today's episode, Amy Walls and Jon Gay look at each of these questions and help you understand what the answers will mean.

Thimbleberry Financial Website

Email Thimbleberry Financial

• Call Thimbleberry Financial at 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

• What is it and how did it become law?
• Changes for small business
• Changes for Required Minimum Distributions (RMD's)
• Changes for traditional IRA contributions
• Changes for 529 College Savings Accounts
• Effects on so-called "Stretch IRAs."
• How the SECURE Act will push people to take a look at their retirement strategies.

Thimbleberry Financial Website

Email Thimbleberry Financial

Call Thimbleberry Financial at 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

• Increase Your Cash Reserve
• Pay Down Your Debt (and how)
• Increase Savings
• Check Your Credit Report
• Review Your Beneficiaries
• Review Insurance Coverages
• Figure out what you spent in 2019, and use it to create a budget for 2020.

Links:

Website: Free Annual Credit Report

Thimbleberry Financial Website

Email Thimbleberry Financial

Call Thimbleberry Financial at 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

The shares don't become the employees until the RSUs vest, which can happen partially or completely as the employee stays longer with the company.

When the shares vest, you are taxed on the value of the stock as regular income. When you sell the shares, you are taxed on the change in the stock price.

For example - at vest, you have 100 shares at $50 per share. That's a value of $5,000.

If you sell the stock when it's at $51 per share, you are taxed on the $1/share gain.

Amy breaks all of this down, including reasons why you may want to hold or sell your RSUs, and when.

Links:

Blog Post on RSU Tax Misconceptions

Thimbleberry Financial Website

Email Thimbleberry Financial

Call Thimbleberry Financial at 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

We also look at other aspects of Roth accounts, including Roth conversions, the "back door Roth," and employer-sponsored Roth plans.

Finally, Amy busts the myths surrounding Roths, including when to contribute and the various tax implications.

As always, you should talk with an advisor who focuses on comprehensive financial planning. They can actually measure the impact of these changes so you can know the impact today, and the impact in the future.

Links:

Thimbleberry Financial Website

Email Thimbleberry Financial

Call Thimbleberry Financial at 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

• Understanding your fears
• Being aware of market influencing factors
• How to be proactive
• Remembering what you control and influence
• The bright side of a downturn (yes, there are some).

Links:

Thimbleberry Financial Website

Email Thimbleberry Financial

Call Thimbleberry Financial at 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

In today's episode, Amy Walls explains the importance of including your insurance needs in your overall financial plan - and just how personal insurance is for her.

Links:

Thimbleberry Financial Website

Email Thimbleberry Financial

Call Thimbleberry Financial at 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Tax Diversification is really a 3-point triangle - Amy explains how this analogy works.

In our first episode, we also cover the approach and importance of tax diversification, including some common misconceptions.

There are some common pitfalls associated with tax-free vehicles.

Finally, Jon and Amy ask the proverbial question: "Should everyone have each type of investment?"

Links:

Thimbleberry Financial Website

Email Thimbleberry Financial

Call Thimbleberry Financial at 503-610-6510

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/