125: Incremental Steps, Lasting Impact: How Small Changes Lead to Financial Success with Meg Wheeler, CPA
Release Date: 12/01/2025
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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“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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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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“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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"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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"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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“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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"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...
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"You need to come up with your own number, not using someone else's, because your situation is going to be different from someone else... and it's going to change over time, and that's still okay." A lot of folks believe that there is a magic number that they need to work towards in order to be able to retire. There is a myth out there that there is some perfect number of dollars you need to accumulate so that you can retire. That it’s really all just one mathematical equation with one distinct, perfect answer. …Except this belief is completely, utterly unfounded....
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“It’s not about deprivation. It’s about balance. It’s about taking care of your today self and your future self.” Join our hosts, Stephanie McCullough of Sofia Financial and Kevin Gaines of American Financial Management Group, as they simplify the world of financial planning, starting with understanding cash flow. They tackle how to monitor the inflow and outflow of your money, without yet worrying about its source or where it's going. Learn the importance of observing more than one month of data, as things can fluctuate from month to month. Stephanie and Kevin...
info_outline“Creating safe spaces for people to talk about money is one of the most powerful things we can do right now to make the world better for change.” -Meg Wheeler
Our hosts Stephanie McCullough and Kevin Gaines sit down with Meg Wheeler, CPA and founder of the Equitable Money Project, who's on a mission to demolish the shame surrounding money conversations through accessible financial education.
Her approach shows us that the path to financial confidence isn't about becoming an expert. It's about learning to simply talk about money without judgment.
"Why should we know this when we've never been taught it in school?"
Meg challenges the pervasive shame many people feel about their financial knowledge gaps. After all, we don't feel ashamed about not knowing brain surgery or environmental science because we were never taught those subjects either!
The real problem isn't lack of knowledge, but the absence of safe spaces to discuss money openly.
Meg's work centers on creating a community where people can share their financial stories without fear. She emphasizes that most people's situations aren't unique. Whether it's medical debt from our broken healthcare system or struggling with inconsistent business income, the factors contributing to financial challenges are systemic rather than personal failures.
She suggests going for incremental progress rather than perfection.
"Every quarter we want you to pick just one thing within one of those buckets to focus on," she explains, referring to her three-pillar framework: set up foundations, stabilize, and grow. This approach makes wealth-building feel achievable rather than overwhelming.
Perhaps most powerfully, Meg advocates for teaching children about money early. Her eight-year-old has a debit card and checks his bank balance before purchases. Not because he's learning to become a financial professional, but because money should not be feared but normalized.
Financial empowerment begins not with expertise, but with conversation, community, and compassion toward ourselves and others navigating the same challenges.
Key Topics
● Meg's Path to Financial Education (02:26)
● The Problem with "Financial Literacy" (04:28)
● Why We Feel Shame About Money (05:21)
● Information vs. Quality Education (05:56)
● Creating Safe Spaces for Money Talk (14:07)
● Teaching Kids About Money (16:13)
● Learning the Language of Money (17:43)
● The Three Pillars of Wealth Building (25:51)
● Overcoming Emergency Fund Shame (26:54)
● Business Owner Tips and Avoidance (33:00)
Resources:
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You can find the transcript and more information about this episode at www.takebackretirement.com.
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