122: Redefining Retirement: Finding Your Creative Voice Through Comedy with Lynn Harris
Release Date: 10/15/2025
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
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“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...
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120: Women, Retirement, and the Lessons of Behavioral Finance (rerun)
Take Back Retirement
“The human brain is actually wired to trip us up, to shoot ourselves in the foot when it comes to money and investing. A little bit of self-examination can help pull us out of these knee-jerk reactions.” Prepare for a knowledge voyage as our hosts Stephanie McCullough and Kevin Gaines redefine retirement for women, bringing insights from behavioral finance, a fascinating field that explores how we make decisions around money. By the end of this episode, you'll have a deeper understanding of financial behaviors and how to make smarter choices. Our hosts dissect the concept of...
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119: Redefining Success and Identity After 50 with Deborah Heiser
Take Back Retirement
“Generativity. Think of it as generating something from yourself and putting it into the world.” Our hosts, Stephanie McCullough and Kevin Gaines, explore the positive side of aging with Dr. Deborah Heiser, an applied developmental psychologist who pivoted from studying depression and Alzheimer's to researching what we actually have to look forward to as we age. "You can run faster than me, but I'm happier than you." Dr. Heiser's transformation began at a dinner party when someone challenged her: "What do we have to look forward to as we age? You are studying everything that...
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118: Reclaiming Life: Lessons from a Gray Divorce Survivor with Pat Fenner
Take Back Retirement
"What I really was grieving was the loss of what I'd hoped my marriage would have been." – Pat Fenner Our hosts, Stephanie McCullough and Kevin Gaines, sit down with author and podcaster Pat Fenner, who shares her powerful journey through "gray divorce"—divorce that happens to women over 50, typically after a decade or more of marriage. After 37 years of marriage, Pat found herself having to start over at an age when most couples are planning retirement together. Her story brings to light the unique challenges facing women in gray divorce, from employment gaps that make renting an...
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117: The Power of Presence: Supporting Those in Grief with Paula Harris
Take Back Retirement
“‘Let me know if you need anything’ is one of the most useless things you can say.” –Paula Harris Our hosts, Stephanie McCullough and Kevin Gaines, sit down with financial advisor and author Paula Harris, who shares practical insights on how to support someone grieving the loss of a spouse. Drawing on years of experience working with widowed clients and her own faith-rooted perspective, Paula shares thoughtful, actionable ways to be present during what can be one of life’s most isolating seasons. Drawing from her publications Rise Up: A Widow’s Journal and A Grief Journal,...
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116: Reimagining Your Next Chapter: Longevity, Intention, and the Power of Yes with Allison Davis
Take Back Retirement
“Body work, brain work, and world work - all longevity habits fit into those three categories.” -Allison Davis When author and naturopath Allison Davis turned 60, she didn't accept it as the “gateway to old age”—she saw it as a turning point. Our hosts, Stephanie McCullough and Kevin Gaines, talk with Allison about her transformative journey and her new book, Sixty Is a Good Start: A Powerful Body, A Purposeful Life, and a Plan to Make It Happen. Allison recounts a yearlong period of reflection that led to saying “yes” to new challenges, most notably, the intense 75 Hard program....
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115: Financial Therapy: The Intersection of Money and Emotions with Wendy Wright
Take Back Retirement
“There is not good or bad with money” Our hosts, Stephanie McCullough and Kevin Gaines, sit down with financial therapist Wendy Wright to unpack the emotional complexities that often underlie our financial behaviors. Wendy believes that money issues aren’t just math problems—they’re emotional ones too! Rather than focusing on dollars and cents alone, Wendy helps her clients understand why they avoid budgeting, overspend in emotional moments, or feel incapable of managing money. Her mantra? “Abundant, compassionate curiosity and zero judgment.” Wendy discusses common patterns like...
info_outline"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 cohort" of women in their forties, fifties, and better who arrive at Gold Comedy with a clear message: "I'm doing this."
These aren't bucket-list dabblers. They're women like Rocky, a retired high school art teacher who came saying, "I know I'm funny, but I don't know how to write a joke." Three years later, she's touring with her half-hour solo show and writing for a sketch team. Or Billie from Portland, whose pilot "Batshit Debbie" is now in development with a well-known comedian attached.
Lynn tells us that comedy serves as more than entertainment.
“Humor,” she says, “inspires trust.” When a comic takes you through a setup to an unexpected punchline, everyone’s connected. "You all who got that joke have something in common," Harris explains.
Technology has democratized access to comedy education. No longer must aspiring comics brave potentially hostile open mics or relocate to major cities. Through Zoom classes and social media, women can develop their craft from home, finding their unique voice without geographic or social barriers.
Most importantly, Harris reminds us that while natural talent helps, comedy is learnable. It requires practice, understanding the science of humor, and most crucially, developing your unique perspective.
That’s something midlife women already possess in abundance!
Key Topics:
- Gold Comedy's Mission and Midlife Students (3:04)
- Empty Nest as Creative Catalyst (6:24)
- Rocky's Journey from Art Teacher to Touring Comic (11:01)
- Can Anyone Learn to Be Funny? (13:42)
- Women Still Facing One-Woman-Per-Show Reality (18:27)
- How Comedy Builds Trust and Connection (27:18)
- Remote Comedy Education Breaking Down Barriers (32:59)
- Stephanie and Kevin's Wrap Up (39:05)
Resources:
- Classes, events, and info at GoldComedy.com
- Gold Comedy on Instagram (DM and mention that you heard Lynn on this episode for a 10% discount!)
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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