127: Conversations That Count: Money, Values, and Clarity with Carl Richards
Release Date: 12/30/2025
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...
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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...
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143: Am I Allowed? The Permission Paradox, with Dan Haylett
Take Back Retirement
“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,...
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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...
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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...
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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...
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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...
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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...
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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....
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136: 10 Things To Do When You're 10 Years Out From Retirement
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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...
info_outline“In a life well lived, there's always going to be more things you may want to do than you can do with time, energy, money, and attention.” -Carl Richards
Stephanie and Kevin welcome Carl Richards, creator of the iconic "Sketch Guy" column in The New York Times, for an inspiring conversation about his latest book, "Your Money: Reimagining Wealth in 101 Simple Sketches." Over 17 years in the making, this collection distills complex financial concepts into simple drawings designed to spark the conversations that truly matter!
Each sketch focuses on a single idea, creating entry points for conversations that words alone can't generate. You won’t get all the answers, but that’s okay! The true goal is to help people start talking about money in meaningful ways.
Stephanie and Kevin explore several of their favorite sketches, beginning with "The Getting Ahead Trap”: a bar graph showing that money needed to "get ahead" has no top, while money needed for "having enough" is surprisingly small.
Makes sense. After all, step zero of financial planning is understanding what's most important to you. Without that clarity, discussions about dollars and vehicles are pointless.
Carl emphasizes that "your values are not at war, they're in conversation". That’s probably his favorite line in the entire book!
"None of us were really taught how to talk about money," Carl reflects, especially the deep conversations about worries and values rather than just CNBC-style market talk.
The book gives us permission to be imperfect. Financial planning is educated guessing, goals are guesses, and things change. Not only is that okay, but it's reality.
Carl encourages "deep hugs and big spreadsheets" when clients need certainty, while gently helping them understand that precision isn't always possible or necessary.
Most importantly, money isn't just math. Algorithms can't feel anxiety about major decisions or pride in achieving goals. Human guidance remains essential, even as technology advances.
Key Topics
· Creating Conversation Starters, Not Answers (03:35)
· The Getting Ahead Trap vs. Having Enough (05:03)
· Real Financial Planning: Money Meets Life (07:27)
· Values in Conversation, Not at War (09:29)
· The Price of Silence About Money (12:29)
· Money Isn't Just Math (15:35)
· Goals Are Guesses (and That's Okay!) (21:30)
· Standing Between Clients and Big Mistakes (27:24)
· Stephanie and Kevin’s Wrap-Up (30:32)
Resources:
· Carl’s Weekly Newsletter, Book, and other Resources
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You can find the transcript and more information about this episode at www.takebackretirement.com.
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