128: Scripts, Frameworks, and Real Talk: Mastering Money Conversations with Erika Wasserman
Release Date: 01/15/2026
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...
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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...
info_outline“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 Money Mindset Method. It’s a five-step framework using the word MONEY itself: Make the conversation comfortable (setting matters!), One question at a time (resist throwing in the kitchen sink), Nurture shared goals (understanding the "why" behind decisions), Evaluate practical solutions (brainstorm separately, then share), and Yes to compassion (for yourself and others).
This repeatable approach gives people tools to practice at home once they've built the confidence.
Erika emphasizes that talking about money is a skill most of us never learned. With 81% of people taught not to discuss finances (without even knowing why), we're left without the vocabulary or framework for these crucial conversations.
Our money mindsets come from our backgrounds, religion, culture, and personal experiences, yet we merge finances with partners who have completely different histories without ever discussing them.
The book includes incredibly practical nuggets such as actual conversation scripts for specific scenarios, visual diagrams showing different ways couples can structure their finances, and the wisdom that what works at 23 won't necessarily work at 40.
When we normalize talking about money, we create ripple effects, modeling healthier relationships with finances for the next generation watching us!
Key Topics
- The Money Mindset Method Framework (07:33)
- Make the Conversation Comfortable (13:34)
- Using “Passwords” to Take Breaks During Hard Talks (21:36)
- Practical Scripts for Real Conversations (24:43)
- Visual Diagrams: Different Ways to Merge Money (27:35)
- Where Money Mindsets Come From (30:34)
- Kevin's and Stephanie's Wrap Up (38:49)
Resources:
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