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136: 10 Things To Do When You're 10 Years Out From Retirement

Release Date: 05/15/2026

145: Your Year-End Financial Checklist: 10 Things to Review Before December

Take Back Retirement

“December is probably too late to scramble around and logistically get stuff done.” Our host Stephanie McCullough counts just nine work weeks left in the year, so she and co-host Kevin Gaines walk through a ten-item year-end checklist. Needless to say, these are best tackled months in advance rather than during the December scramble! They cover the year-end deadlines. Contributions to 401(k)s must land by December 31, even though IRA contributions can wait until April 15, and a bonus paid in January counts toward next year. For 2026, the limit is $24,500, with an $8,000 catch-up from...

144: We Need to Talk About Inheritance!

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“The biggest mistake parents can make is passing down money without communicating the family values that drive your thinking.” Our hosts, Stephanie McCullough and Kevin Gaines, dig into Kiplinger's October cover story on "the great wealth transfer," the slow handoff of an estimated $124 trillion from Baby Boomers to their children and grandchildren. That number is a bit misleading considering more than half of that wealth sits with the richest 2% of households, and a quarter of parents expect to leave less than $100,000. Citing the magazine's survey, roughly two in five families have never...

143: Am I Allowed? The Permission Paradox, with Dan Haylett

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“The one thing you're guaranteed to run out of is time.” Our hosts, Stephanie McCullough and Kevin Gaines, welcome back financial planner Dan Haylett, founder of Humans vs. Retirement and author of The Retirement You Didn't See Coming, to unpack his viral essay "The Permission Paradox." Digging through his own client conversations for patterns, Dan found the two words that came up most were "permission" and "allowed." The people who have saved diligently for decades are often the ones least able to enjoy it, because permission was always external. For them, a paycheck justified spending,...

142: Don’t Wait Until 65: Medicare Planning For Gen X And Beyond with Danielle Kunkle Roberts

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“Everything government touches is complicated.” - Danielle Kunkle Roberts Our hosts, Stephanie McCullough and Kevin Gaines, bring on Danielle Kunkle Roberts of Boomer Benefits, and author of 10 Costly Medicare Mistakes You Can't Afford to Make. As the title of her book suggests, Medicare isn't free. Believing otherwise is mistake number one! Premiums, deductibles, and coverage gaps are real costs that blindside retirees, especially anyone who leaves the workforce before 65 and needs an ACA bridge plan to survive the gap. The trickiest wrinkle is the size-of-employer rule. If you work...

141: Estimating Spending in Retirement Calculations: Front-end the Fun!

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“Spreadsheets are great at math; they suck at flexibility.” Our hosts, Stephanie McCullough and Kevin Gaines, take aim at the assumption that every retiree spends the same inflation-adjusted dollar amount, every year, until death. It's the number your 401(k) statement spits out, the number the 4% rule promises, and it's wrong in two directions at once! First, it ignores life's lumpiness such as the new roof, the wedding, the pandemic-delayed trip to Greece. These are one-off costs that planners can average into projections but never quite eliminate. Second, and more provocatively, it...

140: Don't You Dare Call Me Retired: Amy Bernstein on Creativity, Doubt, and Uncoupling Your Worth From Your Paycheck

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“You need to uncouple your self-worth from your income.” Amy Bernstein does not like the word “retired”. Our hosts, Stephanie McCullough and Kevin Gaines, aren’t too fond of the word either. A former journalist and federal government communications veteran, she didn’t quit anything cold. She shortened her commute first, then went part-time, then, when the pandemic made her last part-time job untenable, took the final step. What followed was less a plan than experiments guided by whatever sparked joy. These “experiments” included playwriting classes, a first novel written on the...

139: What Women Need to Know about Moving Investment Accounts

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“As with all things with the IRS, document, document, document.” Our hosts, Stephanie McCullough and Kevin Gaines, explain what actually happens when you move an investment or retirement account from one custodian to another. The mechanics may seem as simple as filling out a form and waiting a few days. But Kevin walks through the fine print that trips up even seasoned advisors. Taxable accounts can usually move without triggering a sale, so cost basis and unrealized gains transfer intact. Retirement accounts are where the real danger lives. There are two ways to move retirement money: a...

138: What Women Need to Know about the Estate and Gift Tax System (Rerun)

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Today, Stephanie and Kevin cover a topic that can often get confusing for many people: the estate and gift tax system. This is different from the income tax system, and both are federal tax systems that everyone needs to be aware of when planning for retirement. At the end of the day, the IRS is getting paid. The only two questions, then, are: Who pays? and When? Our hosts tackle these questions and more. While today’s discussion is a big picture overview of the estate and gift tax system, it will give you a general grasp of the concepts and vocabulary that will make your next...

137: Rethink Retirement: Taking Charge of Your Next Chapter with Andi Simon

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“Take charge. Your retirement is your time.” Our hosts, Stephanie McCullough and Kevin Gaines, sit down with Dr. Andi Simon, corporate anthropologist and author of Rethink Retirement, whose research offers a bracing corrective to how most people think about life after work. Andi spent years embedding herself in senior living communities on the west coast, interviewing residents who had done everything "right" financially and still found themselves empty, bored, and stripped of identity. Through it all, she’s concluded that retiring from something is not the same as retiring to something....

136: 10 Things To Do When You're 10 Years Out From Retirement

Take Back Retirement

"Don't sit around waiting to feel motivated. You take some little actions, and that often gives you the motivation and the momentum to move forward." Our hosts, Stephanie McCullough and Kevin Gaines, sit down to work through a HerMoney.com list of ten things to do when retirement is a decade away. The meta-lesson turns out to be bigger than any single item on it! The list, from Jean Chatzky's financial information service for women, gives them a useful scaffold, but what they keep returning to is the paralysis that keeps so many people from starting at all. Planning for retirement can feel...

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"Don't sit around waiting to feel motivated. You take some little actions, and that often gives you the motivation and the momentum to move forward."

Our hosts, Stephanie McCullough and Kevin Gaines, sit down to work through a HerMoney.com list of ten things to do when retirement is a decade away. The meta-lesson turns out to be bigger than any single item on it!

The list, from Jean Chatzky's financial information service for women, gives them a useful scaffold, but what they keep returning to is the paralysis that keeps so many people from starting at all. Planning for retirement can feel like pushing a stone uphill; getting moving makes it roll the other way.

The list items themselves span the practical and the personal. Test-drive potential retirement destinations before committing. Tackle home repairs now, while you still have a paycheck. Start volunteering, not just to give back but to road-test how you'll spend your time when work no longer fills it.

On the financial side: understand what Medicare actually covers (spoiler: not dental, vision, or long-term care). Build your HSA if you’re eligible. Track down old 401(k)s and check the beneficiaries on every account. Create your Social Security account online and verify your earnings record for errors. And on claiming age, Kevin pushes back on the blanket advice to "always wait" because Social Security strategy depends on how it fits the rest of your specific plan.

The bonus tip says it all: say it out loud. Telling people you're planning to retire creates accountability. It makes the stone easier to push!

Key Topics:

Trying Out Retirement Destinations (04:32)
Home Repairs, Renovations, and Aging in Place (07:25)
Volunteering: A Test Drive for Your Time (12:11)
Reclaiming Your Calendar… and Your Identity (13:34)
Healthcare Costs, Medicare Myths, and HSAs (16:56)
Building a Social Network Outside the Office (21:11)
Checking In on Pensions and Old 401(k)s (25:23)
Why the 10-Year Mark Is the Right Time to Find a Financial Planner (27:32)
Social Security: "Wait" Is Not a One-Size-Fits-All Answer (29:54)
Creating Your Social Security Account (and Checking Your Earnings Record) (30:47)
Say It Out Loud (32:10)

Resources:

Retirement Readiness Quiz: https://www.aarp.org/money/retirement/readiness-quiz/
The 5 Years Before You Retire and other books by Emily Guy Birken: https://www.emilyguybirken.com/books
HerMoney.com Article Discussed in this Episode: https://hermoney.com/invest/10-things-you-should-do-when-retirement-is-10-years-away/

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You can find the transcript and more information about this episode at www.takebackretirement.com.

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