The Retirement Voyage with Dale McGregor

Parting Words

caleb@paperbackexpert.com (Caleb DeLon) — Wed, 8 Apr 2026 04:00:00 +0000

Bestselling Author and Retirement Expert, Dale McGregor, shares his closing guidance from The Retirement Voyage. He highlights the danger of universal “always” or “never” financial advice and explains why fiduciaries must understand each client’s complete picture before making recommendations. Dale describes how his team uses advanced planning software to model market downturns, rising healthcare costs, long-term care events, and other retirement “storms.” With the right guidance, retirees can chart a personalized route that leads to stability, security, and confidence.

Federal Employees' Group Life Insurance

caleb@paperbackexpert.com (Caleb DeLon) — Wed, 1 Apr 2026 04:00:00 +0000

Bestselling Author and Retirement Expert, Dale McGregor, breaks down FEGLI—how it works, why it's affordable early in a federal career, and how hidden price increases erode its value over time. He explains the five-year premium jumps, the sticker shock many employees discover in their 50s and 60s, and why most retirees cannot afford FEGLI later in life. Dale also covers strategies to preserve a portion of coverage at no ongoing cost and why employees should never cancel FEGLI without a replacement in place.

The Fedral Employees Health Benefits (FEHB) Program

caleb@paperbackexpert.com (Caleb DeLon) — Wed, 25 Mar 2026 04:00:00 +0000

Bestselling Author and Retirement Expert, Dale McGregor, walks through the Federal Employees Health Benefits (FEHB) program and why it remains one of the most valuable benefits in federal service. He explains government premium contributions, coverage options, and why FEHB becomes a strategic asset in retirement. Dale also details how Medicare and TRICARE integrate, including the little-known ability to suspend (not cancel) FEHB—preserving future access without penalty. This episode highlights why federal employees can’t rely on agencies for personalized advice.

Federal Employee Need to Knows: The Thrifft Savings Plan for Federal Employees

caleb@paperbackexpert.com (Caleb DeLon) — Wed, 18 Mar 2026 04:00:00 +0000

Bestselling Author and Retirement Expert, Dale McGregor, explains why he began specializing in federal employee benefits more than a decade ago—and why this group desperately needs clear retirement guidance. He breaks down the Thrift Savings Plan, its five simple fund options, government matching rules, lifecycle funds, and key differences from traditional 401(k)s. Dale also warns about upcoming Roth conversion changes, distribution limitations, and traps that can lock employees into irreversible mistakes.

Roth Conversions and Retirement Planning

caleb@paperbackexpert.com (Caleb DeLon) — Wed, 11 Mar 2026 04:00:00 +0000

Bestselling Author and Retirement Expert, Dale McGregor, digs into Roth conversions and why he believes everyone who’s eligible should consider having Roth money. He contrasts traditional tax-deferred accounts—sold on the promise of lower taxes in retirement—with today’s reality of rising tax pressure. Dale explains how to strategically convert portions of pre-tax accounts to Roth over time, how to watch your tax brackets while you do it, and the role of required minimum distributions at age 73. With careful planning, Roth conversions can shrink or even eliminate future RMDs and build a pool of tax-free income for later years.

Living Trusts

caleb@paperbackexpert.com (Caleb DeLon) — Wed, 4 Mar 2026 05:00:00 +0000

Bestselling Author and Retirement Expert, Dale McGregor, explains why understanding “the flow of money when you die” matters. He outlines how assets pass to a joint owner, to named beneficiaries, or through probate—and where living trusts fit in. Dale breaks down revocable versus irrevocable trusts, how trustees carry out your wishes, and why a will alone still forces your family through probate court. He uses the high-profile example of musician Prince to show how poor planning can cost heirs years of delay and tens of millions in legal fees and taxes.

Medicare and Medicaid

caleb@paperbackexpert.com (Caleb DeLon) — Wed, 25 Feb 2026 05:00:00 +0000

Bestselling Author and Retirement Expert, Dale McGregor, sorts out the confusion between Medicare and Medicaid.He explains that Medicare is a federal program you’ve paid into, while Medicaid is a state-run safety net that kicks in when your resources run low. They talk through Medicare Parts A and B, the income-related costs for Part B, and the dizzying array of supplemental and Advantage plans. Dale stresses the importance of enrollment windows around age 65 and why delays in certain parts can trigger permanent penalties.

Social Security and When to Claim It

caleb@paperbackexpert.com (Caleb DeLon) — Wed, 18 Feb 2026 05:00:00 +0000

Bestselling Author and Retirement Expert, Dale McGregor, tackles the classic question: “When should I claim Social Security?” After joking that he can give you the perfect answer if you tell him the date you’ll die, he lays out a practical framework. Dale explains why Social Security is best viewed as a budget item—if your plan needs the income at 62, you turn it on; if you can wait, you may benefit from higher checks later. He also unpacks the earnings test between 62 and full retirement age, and how couples can use strategies like spousal benefits to maximize household income.

The Horizon: Plan for Long-Term Care and Unexpected Medical Expenses

caleb@paperbackexpert.com (Caleb DeLon) — Wed, 11 Feb 2026 05:00:00 +0000

Bestselling Author and Retirement Expert, Dale McGregor, looks toward the retirement “horizon” and tackles one of the biggest threats to your nest egg: long-term care and unplanned medical expenses. Dale shares the startling stat that people who live past 65 have about a 70% chance of needing some form of long-term care. He explains what qualifies as long-term care, how quickly a $10,000-per-month nursing home bill can exhaust a million-dollar portfolio, and why he often prefers max-funded life insurance strategies over traditional “use it or lose it” long-term care policies.

Setting Sail: Annuities

caleb@paperbackexpert.com (Caleb DeLon) — Wed, 4 Feb 2026 05:00:00 +0000

Bestselling Author and Retirement Expert, Dale McGregor, demystifies annuities. He explains that “annuity” simply means a lifetime payment stream—and that Social Security and many pensions are, in fact, annuities. He draws a sharp line between high-fee, restrictive products you should avoid and the modern annuities that can protect principal, provide guaranteed lifetime income, and even boost payouts if you need long-term care. Dale stresses that the key is matching the right annuity to your situation rather than blindly accepting or rejecting the entire category.

Establishing Guaranteed Streams of Income

caleb@paperbackexpert.com (Caleb DeLon) — Wed, 28 Jan 2026 05:00:00 +0000

Bestselling Author and Retirement Expert, Dale McGregor, talks about how retirement income has changed over the past few decades—from traditional pensions to today’s world of 401(k)s and IRAs. He explains why guaranteed income matters so much psychologically and practically, and why most people actually spend more in retirement, not less. Dale walks through how he models income out to age 100 so clients can see whether they’re on track and how debt reduction fits into building realistic, sustainable income.

Constructing Your Fiscal House

caleb@paperbackexpert.com (Caleb DeLon) — Wed, 21 Jan 2026 05:00:00 +0000

Bestselling Author and Retirement Expert, Dale McGregor, introduces the concept of your “fiscal house.” He explains why you never start building with the roof and shows how to think of your money in three layers: foundation (low-risk, steady vehicles), walls (your daily-life cash and savings), and roof (higher-risk growth assets). Dale warns how strong markets—like 2025—can tempt people to strip their foundation to overbuild the roof, and why that decision often backfires when markets turn.

How to Plan for Unexpected Expenses

caleb@paperbackexpert.com (Caleb DeLon) — Wed, 14 Jan 2026 05:00:00 +0000

Bestselling Author and Retirement Expert, Dale McGregor, reframes “unexpected” expenses as often “unplanned” expenses—especially in the medical arena. He shares his own story of landing in an ambulance next to his son and talks through real-world shocks like surgeries, joint replacements, new medications, and long-term care. Dale explains why the old “just save” approach isn’t enough anymore and shows how modern tools—especially certain types of life insurance—can pull double or triple duty for protection, accumulation, and tax-free access.

Mitigating Risk

caleb@paperbackexpert.com (Caleb DeLon) — Wed, 7 Jan 2026 05:00:00 +0000

Bestselling Author and Retirement Expert, Dale McGregor, defines what “risk” really means in retirement and compares it to how insurance companies spread risk. He unpacks longevity risk, market risk, withdrawal rate risk, and inflation, and explains how they interact. Dale also talks about why you can’t “time the market,” why COLAs don’t truly keep up with inflation, and why knowing your personal risk tolerance is critical.

Is Debt Good or Bad?

caleb@paperbackexpert.com (Caleb DeLon) — Sat, 3 Jan 2026 05:00:00 +0000

Bestselling Author and Retirement Expert, Dale McGregor, explains why the real answer to “Is debt good or bad?” is “it depends.” He walks through when debt can be strategically useful—like tax-deductible mortgage interest or 0% auto loans—and when it quietly sabotages your financial future, like revolving credit card balances and chronic car trading. Dale also talks about how to think differently about student loans and why your debt strategy needs to change as you move closer to retirement.

Taking Stock: Creating a Budget

caleb@paperbackexpert.com (Caleb DeLon) — Wed, 24 Dec 2025 05:00:00 +0000

Bestselling Author and Retirement Expert, Dale McGregor,explains why a budget isn’t punishment but a roadmap that tells your money where to go instead of wondering where it went. He compares budgeting to using GPS on a road trip: it helps you navigate detours and reach your destination on purpose. Dale walks through a practical starting point—tracking every cent you spend for 1–2 months, categorizing it, and then deciding what truly matters. Along the way, he shares stories of envelope systems, gas-station “miscellaneous” spending, and how disciplined tracking helped wipe out debt and create room to invest for the future.

Unexpected Events: Resetting the Coordinates

caleb@paperbackexpert.com (Caleb DeLon) — Wed, 17 Dec 2025 05:00:00 +0000

Bestselling Author and Retirement Expert, Dale McGregor, shares the dramatic story behind the opening of his book The Retirement Voyage: the night his son suffered a severe hip injury on the field and, moments later, Dale shattered his own hip jumping from the bleachers. He walks through the surgeries, the long recovery, and the surprise diagnosis that followed. Dale then connects this “wacko night” to the core of his financial planning philosophy: life throws curveballs, and without a written plan and built-in flexibility, one unexpected event can derail your future.