127: Conversations That Count: Money, Values, and Clarity with Carl Richards
Release Date: 12/30/2025
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...
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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...
info_outline“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 conversations that words alone can't generate. You won’t get all the answers, but that’s okay! The true goal is to help people start talking about money in meaningful ways.
Stephanie and Kevin explore several of their favorite sketches, beginning with "The Getting Ahead Trap”: a bar graph showing that money needed to "get ahead" has no top, while money needed for "having enough" is surprisingly small.
Makes sense. After all, step zero of financial planning is understanding what's most important to you. Without that clarity, discussions about dollars and vehicles are pointless.
Carl emphasizes that "your values are not at war, they're in conversation". That’s probably his favorite line in the entire book!
"None of us were really taught how to talk about money," Carl reflects, especially the deep conversations about worries and values rather than just CNBC-style market talk.
The book gives us permission to be imperfect. Financial planning is educated guessing, goals are guesses, and things change. Not only is that okay, but it's reality.
Carl encourages "deep hugs and big spreadsheets" when clients need certainty, while gently helping them understand that precision isn't always possible or necessary.
Most importantly, money isn't just math. Algorithms can't feel anxiety about major decisions or pride in achieving goals. Human guidance remains essential, even as technology advances.
Key Topics
· Creating Conversation Starters, Not Answers (03:35)
· The Getting Ahead Trap vs. Having Enough (05:03)
· Real Financial Planning: Money Meets Life (07:27)
· Values in Conversation, Not at War (09:29)
· The Price of Silence About Money (12:29)
· Money Isn't Just Math (15:35)
· Goals Are Guesses (and That's Okay!) (21:30)
· Standing Between Clients and Big Mistakes (27:24)
· Stephanie and Kevin’s Wrap-Up (30:32)
Resources:
· Carl’s Weekly Newsletter, Book, and other 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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