124: Leap Smart: Career Transitions and Financial Strategies for Midlife Women with Tabatha Jones
Release Date: 11/15/2025
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...
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132: What's Your Number? (rerun)
Take Back Retirement
"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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131: Back to Basics: Essential First Steps to Taking Control of Your Finances (rerun)
Take Back Retirement
“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"It is never too late to start something new and to put your energy into something that you’ve loved your whole life, but you’ve never had time to focus on."
Our hosts, Stephanie McCullough and Kevin Gaines, explore the strategic path to entrepreneurship in midlife with the Corporate Escape Sherpa herself, Tabatha Jones!
After 30 years in corporate tech leadership, Tabatha made her leap at age 50 and now guides women through building profitable businesses before they leave their steady paychecks behind.
"If it's not on your calendar, if it's not something you are focused on doing, it just becomes a someday, which becomes a never, which becomes regret."
Tabatha's approach challenges the typical entrepreneurial narrative. Rather than dramatic leaps of faith, she advocates for methodical preparation while your corporate job finances your dream. She saved three years of expenses before leaving, far beyond the typical 6-12 months, and systematically eliminated debt, paid off her house, and even installed solar panels to reduce future living costs.
Her "Freedom Framework" starts with the crucial question of "why", and she insists on going at least five layers deep.
"When you stay at that surface level why... it's not enough to keep you going," Tabatha explains. From there, entrepreneurs identify their "what" (skills and gifts), "who" (ideal clients), and finally "how" (the business model). In that order!
Chances are, you need a financial reality check as a prerequisite to creating your freedom plan. Tabatha has clients highlight every expense on their credit card statements, hunting for "money leaks" like forgotten subscriptions. One client discovered three gym memberships she'd forgotten about. Another realized her pricing meant she'd need 100 clients monthly just to break even!
Most powerfully, Tabatha reminds us that midlife career changes require different strategies than younger transitions. While thirty-somethings can "dip their toe" in entrepreneurship and return to corporate easily, the job search for midlifers now takes 8-12 months.
Building your business foundation while employed isn't just smart. It's essential!
Key Topics
- The Corporate Escape Sherpa Philosophy (02:17)
- Tabatha's Journey Through 2020 Pandemic Pivot (03:30)
- The Freedom Framework (08:44)
- Why Midlife Transitions Need Different Strategies (09:49)
- Finding Money Leaks and Financial Planning (19:18)
- Client Success Story: Travel Agency Launch (30:37)
- Celebrating Wins and Managing Entrepreneurial Mindset (32:48)
- Stephanie and Kevin's Takeaways (38:10)
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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