124: Leap Smart: Career Transitions and Financial Strategies for Midlife Women with Tabatha Jones
Release Date: 11/15/2025
130: Planning to Age Well: Life Care, Long-term Care, and Advocacy with Laura Lynn Morrissey
Take Back Retirement
“A lot of women feel as though this is ‘my role, this is my job, and if I have to ask for help, there's something wrong with me.’ It doesn't mean failure. It just means that you're taking care of yourself as well as your loved ones.” - Laura Lynn Morrissey Our hosts, Stephanie McCullough and Kevin Gaines, sit down with Laura Lynn Morrissey, founder of Silver Savvy. She brings a unique perspective, combining two decades at Fidelity Investments with hands-on experience building and selling home care companies in Boston! Laura Lynn's journey into senior care began while simultaneously...
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129: What Women Need to Know About Charitable Giving and Retirement
Take Back Retirement
“There are ways to get some more net dollars to the charity, having a smaller financial impact on your own situation. It just takes a little bit of looking at [your financial situation].” Our hosts Stephanie McCullough of Sofia Financial and Kevin Gaines of American Financial Management Group tackle the ins-and-outs of charitable giving, and reveal how strategic planning can maximize impact while preserving your financial security. While charities treat all dollars equally (they pay zero taxes), how you give dramatically affects your bottom line! First up, they cover critical 2026 tax...
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128: Scripts, Frameworks, and Real Talk: Mastering Money Conversations with Erika Wasserman
Take Back Retirement
“My goal in life, my purpose in life, is to spark conversations. And in 2026, my goal is to spark 10,000 financial conversations.” -Erika Wasserman Our hosts, Stephanie McCullough and Kevin Gaines, welcome back financial therapist Erika Wasserman to discuss her groundbreaking new book Conversations with Your Financial Therapist. Invited by Wiley Publishing to write about the emotional side of money, Erika created a practical guide wrapped in storytelling, featuring seven composite characters navigating real financial conversations throughout their lives. The heart of the book is the...
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127: Conversations That Count: Money, Values, and Clarity with Carl Richards
Take Back Retirement
“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...
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126: Retiring Gen X Style: From Anxiety to Action with Kerry Hannon and Janna Herron
Take Back Retirement
“This is a generation that is incredibly scrappy. This is a generation that gets it done. We actually know how to find the resources when we need to.” – Kerry Hannon Our hosts, Stephanie McCullough and Kevin Gaines, welcome Kerry Hannon and Janna Herron, co-authors of "Retirement Bites: A Gen X Guide to Securing Your Financial Future," for a candid conversation about why this overlooked generation faces unique retirement challenges, and why there's still plenty of time to turn things around! The timing couldn't be better. With the oldest Gen Xers turning 60 this year, this generation...
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125: Incremental Steps, Lasting Impact: How Small Changes Lead to Financial Success with Meg Wheeler, CPA
Take Back Retirement
“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...
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124: Leap Smart: Career Transitions and Financial Strategies for Midlife Women with Tabatha Jones
Take Back Retirement
"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...
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123: Making Your Own Story: Finding Meaning After 50 with Diane Gansauer
Take Back Retirement
“You don’t build courage by avoiding what you’re afraid of. You build courage by moving through it.” -Diane Gansauer Our hosts, Stephanie McCullough and Kevin Gaines, explore an extraordinary midlife reinvention with Diane Gansauer, who traded a high-profile government position for one of the few full-time funeral celebrant roles in the United States. Her transformation proves that stepping away from prestige can lead to real personal fulfillment! "I became more effective and a happier person," Diane reflects on leaving her role as deputy director of a Colorado state agency...
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122: Redefining Retirement: Finding Your Creative Voice Through Comedy with Lynn Harris
Take Back Retirement
"Comedy is power because when you make people laugh, you make people listen." -Lynn Harris Our hosts, Stephanie McCullough and Kevin Gaines, explore the unexpected world of midlife comedy careers with Lynn Harris! She’s the founder of Gold Comedy, a comedy school and professional network specifically designed for women and non-binary creators seeking to build comedy careers or creative side hustles. Lynn's journey from journalist and standup comic is proof that midlife transitions can be moments of opportunity and not just crisis. She describes a "very vocal, powerful, creative, awesome...
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121: Radical Transparency: Diane di Costanzo’s Real Retirement Story
Take Back Retirement
“Stop stopping. If something is stopping you from doing this thing you know you should do, just stop stopping.” - Diane di Costanzo Former Chief Content Officer and Financial Journalist Diane di Costanzo proves it's never too late to take control of your financial future! Our hosts, Stephanie McCullough and Kevin Gaines, chat with her in this inspiring episode of Take Back Retirement. At 48, she had saved just $28,000 for retirement. It’s a number that felt shamefully inadequate against the backdrop of million-dollar retirement commercials. Yet eighteen years later, she successfully...
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:
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You can find the transcript and more information about this episode at www.takebackretirement.com.
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