"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. [email protected]

You can find the transcript and more information about this episode at www.takebackretirement.com.

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"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 of approximately 64-65 million Americans born between 1965 and 1980 finds itself squeezed between caring for aging parents and supporting adult children while confronting their own retirement reality.

"We were kind of the Guinea pig generation when it came to the 401(k)s," Janna explains. Gen X caught the worst of both worlds: pensions were disappearing while 401(k)s were arriving without proper education about their importance. Early contribution limits were low, automatic enrollment didn't exist, and many default investment options were conservative money markets rather than growth-oriented funds.

But Kerry and Janna reject the doom-and-gloom narrative. "This is a generation that is incredibly scrappy," Kerry insists. "This is a generation that gets it done."

They believe in starting with vision before worrying about numbers. If you don't know what you're saving for, it's super hard to get excited about doing it. Kerry encourages vision boards and refrigerator lists of life experiences you don't want to miss.

Janna shares how she and her husband hold quarterly "financial summits" and maintain a separate savings account for their dream teardrop camper. "It's fun to look at our little savings fund and go, look how much closer we are."

Retirement doesn't mean stopping work entirely, but reimagining what it means to work! Knowledge workers can transition to consulting, pursue deferred dreams, or explore new fields. The key is planning ahead and continuing to learn.

Perhaps most importantly, they stress addressing health now. Retirement is the time when you can get your health together so that you have better health outcomes when you get older, and save money at the same time.

Gen X's cynicism might be legendary, but channeling that scrappy, resilient spirit could be exactly what secures their financial future!

Key Topics:

· Why a Book for Gen X Now (1:40)

· The 401(k) Guinea Pig Generation (4:39)

· Home Equity as a Bright Spot (12:05)

· Creating Your Retirement Vision (15:07)

· Working Longer as Strategy (21:43)

· AI and the Future of Work (28:29)

· Finding the Right Financial Advisor (30:47)

· Healthcare: The Hidden Retirement Cost (37:21)

· Stephanie and Kevin's Wrap Up (38:44)

Resources:

· Retirement Bites: A Gen X Guide to Securing Your Financial Future (book)

· Kerry Hannon (website)

· Janna Herron (LinkedIn)

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. [email protected]

You can find the transcript and more information about this episode at www.takebackretirement.com.

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"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 been taught it in school?"

Meg challenges the pervasive shame many people feel about their financial knowledge gaps. After all, we don't feel ashamed about not knowing brain surgery or environmental science because we were never taught those subjects either!

The real problem isn't lack of knowledge, but the absence of safe spaces to discuss money openly.

Meg's work centers on creating a community where people can share their financial stories without fear. She emphasizes that most people's situations aren't unique. Whether it's medical debt from our broken healthcare system or struggling with inconsistent business income, the factors contributing to financial challenges are systemic rather than personal failures.

She suggests going for incremental progress rather than perfection.

"Every quarter we want you to pick just one thing within one of those buckets to focus on," she explains, referring to her three-pillar framework: set up foundations, stabilize, and grow. This approach makes wealth-building feel achievable rather than overwhelming.

Perhaps most powerfully, Meg advocates for teaching children about money early. Her eight-year-old has a debit card and checks his bank balance before purchases. Not because he's learning to become a financial professional, but because money should not be feared but normalized.

Financial empowerment begins not with expertise, but with conversation, community, and compassion toward ourselves and others navigating the same challenges.

● Meg's Path to Financial Education (02:26)

● The Problem with "Financial Literacy" (04:28)

● Why We Feel Shame About Money (05:21)

● Information vs. Quality Education (05:56)

● Creating Safe Spaces for Money Talk (14:07)

● Teaching Kids About Money (16:13)

● Learning the Language of Money (17:43)

● The Three Pillars of Wealth Building (25:51)

● Overcoming Emergency Fund Shame (26:54)

● Business Owner Tips and Avoidance (33:00)

Resources:

• Equitable Money Project website

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. [email protected]

You can find the transcript and more information about this episode at www.takebackretirement.com.

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"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:

· Tabatha Jones on LinkedIn

· CorporateEscapeSherpa.com

· Freedom Builder System

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. [email protected]

You can find the transcript and more information about this episode at www.takebackretirement.com.

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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 overseeing multimillion-dollar conservation grants. The political pressures and visibility of managing programs for Great Outdoors Colorado had worn thin.

"What I liked best was really the work one-on-one with families," she says.

Her journey to funeral celebrancy began serendipitously when a wealthy philanthropist, whose ranch had received conservation grants, learned about her occasional memorial officiating. This connection led to a position with North America's largest funeral services provider, where she ultimately celebrated over 400 lives.

The role required mastering the art of storytelling. Working with grieving families, she learned to capture the essence of lives lived. That's a skill that demands deep listening and authentic connection. This was intimate work that stood in stark contrast to her previous bureaucratic responsibilities.

But Diane's reinvention didn't stop there. Upon retirement, she embarked on the Continental Divide Trail, completing 3,100 miles from the Mexico border to Canada.

"It doesn't matter what other people are doing, it's between you and the mountain."

Her experiences culminated in her book "The Waypoints," in which she weaves together insights from honoring 400 lives and conquering thousands of miles of trail.

Midlife transitions aren't about climbing higher on conventional ladders. Sometimes they're about finding entirely different mountains to climb, ones that align with who we're becoming rather than who we thought we should be!

Key Topics

● Career Transition from State Government (3:45)

● Becoming a Funeral Celebrant (6:00)

● Learning the Art of Life Stories (9:53)

● Diane's Process of Working with Clients (17:57)

● Why Diane Wrote Her Book (23:24)

● Continental Divide Trail Challenge (28:15)

● Kevin and Stephanie's Wrap Up (46:58)

Resources:

• The Waypoints: From 400 Farewells and 3,000 Miles (book) • Diane Gansauer on Substack

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. [email protected]

You can find the transcript and more information about this episode at www.takebackretirement.com.

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"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. [email protected]

You can find the transcript and more information about this episode at www.takebackretirement.com.

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"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 retired and embarked on a four-and-a-half-month adventure across Asia and East Africa.

Diane was awarded Content Marketer of the Year in 2022 by the Content Marketing Institute and served as Chief Content Officer at Foundry 360, part of Dotdash Meredith. Her transformation began with a simple conversation with a financial advisor who reframed her situation: she had no debt and some savings.

Her philosophy of "radical transparency" about money emerged from her work editing Millie, a financial magazine for women, where she discovered that not talking about money perpetuates inequality and ignorance. She practices what she preaches, openly sharing specific numbers about her savings and even publishing her daughter's wedding budget in a magazine article.

The key to her success wasn't complex financial wizardry but consistent action. She maximized employer 401(k) matches, utilized catch-up contributions after 50, and became an evangelist for Health Savings Accounts. This account offers "quadruple tax-free" benefits when contributed through payroll deduction by avoiding federal income tax, FICA taxes, while providing tax-free growth and tax-free withdrawals for medical expenses.

Her mantra "stop stopping," captures the paralysis many feel about retirement planning.

As Diane tells us, small amounts invested consistently over time create meaningful wealth, finding the right financial advisor is about personality fit as much as expertise, and retirement timing isn't always perfect.

Key Topics

• Travel Adventures and Retirement Celebration (04:43)
• Radical Transparency About Money (08:08)
• Starting Retirement Savings at 48 (11:00)
• "Stop Stopping" Philosophy (15:30)
• Health Savings Accounts Benefits (17:08)
• Sequence of Return Risk Discussion (24:11)
• Finding the Right Financial Advisor (29:06)
• Stephanie and Kevin's Wrap Up (37:06)

Resources:

• DianeDico.com
• @dianedico on Instagram
• Diane on LinkedIn

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. [email protected]

You can find the transcript and more information about this episode at www.takebackretirement.com.

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"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 the gambler's fallacy to shed light on their own decision-making patterns, with Kevin sharing a personal anecdote to highlight its real-life impact. Following that, prepare for a compelling discussion on mental accounting, a concept that will change how you view your money's value depending on its source. Our hosts explore a study that reveals intriguing patterns in spending "found money" versus hard-earned cash. To wrap up, they look at practical ways to leverage mental accounting in creating a budget and improving your chances of financial success. This episode is a journey toward financial empowerment.

Key Topics:

• Intro to Behavioral Finance (03:10)
• Biases (07:33)
• Recency Bias (AKA Availability Bias) (15:44)
• Mental Accounting (18:42)
• Flipping These Findings to Our Advantage (Action Steps) (25:55)

Resources:

• Predictably Irrational (book)
• Seinfeld Skit: Even Steven

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. [email protected]

You can find the transcript and more information about this episode at www.takebackretirement.com.

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"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 scares us." This moment sparked her journey into understanding generativity—an emotional developmental milestone we reach in midlife where we feel compelled to give back and make our mark on the world.

The conversation reveals a powerful truth: we're biologically programmed to become happier and more fulfilled as we age. This isn't the superficial happiness of opening presents, but the deep satisfaction of asking "Did I matter?" and finding ways to generate impact. Whether through podcasting, volunteering, or passing down family recipes on grandmother's index cards, we're all engaging in mentorship, often without realizing it.

Dr. Heiser makes a crucial distinction between doing your job and true mentoring. A teacher advising students is working; mentoring happens outside the classroom, through voluntary emotional connections. Her book "The Mentorship Edge" helps readers recognize and quantify their impact, filling what she calls their "impact bank."

Most importantly, she reminds us that midlife identity shifts aren't crises but opportunities to pull forgotten aspects of ourselves from the back of the closet and engage parts of our identity we've neglected while surviving our earlier years.

Key Topics:

• Why We Get Happier as We Age (03:08)
• Understanding Generativity and the Difference Between Generous and Generative (11:07)
• Identity Shifts in Midlife (17:11)
• Family Traditions as Mentorship (22:53)
• Mentorship vs. Doing Your Job (23:30)
• Reframing Negative Perspectives on Aging (25:46)
• Stephanie and Kevin's Wrap-Up (36:30)

Resources:

• Dr. Deborah Heiser on Psychology Today
• On LinkedIn
• Her Website
• The Mentorship Edge (book)

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. [email protected]

You can find the transcript and more information about this episode at www.takebackretirement.com.

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"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 apartment nearly impossible to the crushing blow to self-worth that comes with feeling "unemployable" after decades focused on family.

Pat's transformation from feeling like she'd "end up being a greeter at Walmart" to building a successful podcast production business offers hope and practical wisdom. Her journey highlights hidden skills many women possess but don't recognize—skills developed through years of unpaid but invaluable work managing households, raising children, and caring for aging parents.

Perhaps most powerfully, Pat discusses reclaiming her identity and becoming what she calls the family "matriarch," which is not someone who controls, but someone who serves by sharing hard-won wisdom. Her advice to women in similar situations is to take inventory of your skills, involve yourself in family finances before you have to, and remember that "being a grown ass woman" isn't selfish. It's actually inspiring!

Key Topics

• "What the Heck is Gray Divorce?" (03:46)
• Employment and Housing Challenges (05:44)
• The Emotional Toll and Self-Image Impact (06:17)
• Discovering Hidden Skills and New Purpose (18:59)
• Overcoming Financial Shame (22:58)
• Redefining Retirement Goals (25:17)
• Embracing the Role of Matriarch (31:20)
• Stephanie and Kevin's WrapUp (35:49)

Resources:

• ReBuilding Your Life After a Gray Divorce (book)
• Pat Fenner Website
• Pat Fenner Gray Resources
• Silver Women with a Bright Future Podcast

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. [email protected]

You can find the transcript and more information about this episode at www.takebackretirement.com.

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