127: Conversations That Count: Money, Values, and Clarity with Carl Richards
Release Date: 12/30/2025
142: Don’t Wait Until 65: Medicare Planning For Gen X And Beyond with Danielle Kunkle Roberts
Take Back Retirement
“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!
Take Back Retirement
“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
Take Back Retirement
“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
Take Back Retirement
“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)
Take Back Retirement
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
Take Back Retirement
“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
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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135: Smarter Social Security: Getting What's Yours Without Panicking
Take Back Retirement
"It's all about these different pieces and how they can fit together. And it's not just how they fit together in good ways, but also how they fit together in bad ways." Our hosts, Stephanie McCullough and Kevin Gaines, sit down to unpack a letter from a reader of The Retirement Strategy Report who signed off as "Get What's Mine Before It's Gone", ready to claim at 62 just to lock in something before the trust fund runs dry. That reader is right to be anxious. The Social Security OASI Trust Fund is now projected to deplete by 2033, at which point ongoing tax revenues would cover only...
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134: Impact Investing for the Rest of Us: Making a Difference Without Millions with Missy Sue Mastel
Take Back Retirement
“If you are feeling that you are not powerful, you are wrong. You are very powerful just in and of yourself. And in community, it's just multiplied.” - Missy Sue Mastel Most people think impact investing is only for the ultra-wealthy. Missy Sue Mastel, a financial strategist with three decades in nonprofit capacity building, disagrees. Our hosts, Stephanie McCullough and Kevin Gaines, welcome Missy to explore how everyday investors and retirees can drive meaningful change without writing a massive check. The conversation centers on what Missy calls "hypergrowth capitalism": a system so...
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133: Don’t Panic, Pause: Simple Steps to Avoid Being Scammed
Take Back Retirement
"Scammers rely on emotion. If they can catch you in that half second of panic, then they might be able to get you to do something.” 41% of American adults have lost money to scams. And that's only those who reported it. Our hosts, Stephanie McCullough and Kevin Gaines, are back to talk all about money scams because the problem keeps growing, and because the scammers, as Kevin puts it, keep learning. The core mechanism hasn't changed either. Scams are all about manufactured panic. Whether it's a Social Security alert, a fake IRS demand, or a "computer security team" that called out of nowhere...
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
If you like what you’ve been hearing, we invite you to subscribe on your favorite platform and leave us a review. Tell us what you love about this episode! Or better yet, tell us what you want to hear more of in the future. stephanie@sofiafinancial.com
You can find the transcript and more information about this episode at www.takebackretirement.com.
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