You’re a woman on the cusp of “retirement” naturally feeling some anxiety. We are two financial planners who take this subject seriously (but ourselves less so). We will help you feel more confident about your choices by cutting through the myths and mysteries. Through conversations and interviews with both subject-experts and women who have gone through what you are approaching, you will have the correct information and motivation to be in control of your future.
Dec 01, 2025
"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. Key Topics ● 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. stephanie@sofiafinancial.com You can find the transcript and more information about this episode at www.takebackretirement.com. Follow Stephanie on Twitter, Facebook, YouTube and LinkedIn. Follow Kevin on Twitter, Facebook, YouTube and LinkedIn.
00:00:41
Nov 18, 2025
"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. stephanie@sofiafinancial.com You can find the transcript and more information about this episode at www.takebackretirement.com. Follow Stephanie on Twitter, Facebook, YouTube and LinkedIn. Follow Kevin on Twitter, Facebook, YouTube and LinkedIn.
00:00:43
Nov 15, 2025
"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. stephanie@sofiafinancial.com You can find the transcript and more information about this episode at www.takebackretirement.com. Follow Stephanie on Twitter, Facebook, YouTube and LinkedIn. Follow Kevin on Twitter, Facebook, YouTube and LinkedIn.
00:00:43
Oct 31, 2025
"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. stephanie@sofiafinancial.com You can find the transcript and more information about this episode at www.takebackretirement.com. Follow Stephanie on Twitter, Facebook, YouTube and LinkedIn. Follow Kevin on Twitter, Facebook, YouTube and LinkedIn.
00:00:50
Oct 31, 2025
"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 (2:04) ● Finding Joy in Personal Work vs Politics (3:30) ● The Wealthy Philanthropist Connection (4:26) ● Becoming a Funeral Celebrant (6:40) ● Learning the Art of Life Stories (10:15) ● Diane's Process of Working with Clients (18:40) ● Why Diane Wrote Her Book (26:10) ● Continental Divide Trail Challenge (35:42) ● "You and the Mountain" Philosophy (51:37) 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. stephanie@sofiafinancial.com You can find the transcript and more information about this episode at www.takebackretirement.com. Follow Stephanie on Twitter, Facebook, YouTube and LinkedIn. Follow Kevin on Twitter, Facebook, YouTube and LinkedIn.
00:00:50
Oct 15, 2025
"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. Follow Stephanie on Twitter, Facebook, YouTube and LinkedIn. Follow Kevin on Twitter, Facebook, YouTube and LinkedIn.
00:00:44
Oct 01, 2025
“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 (04:49) ● Radical Transparency About Money (08:20) ● Starting Retirement Savings at 48 (11:40) ● "Stop Stopping" Philosophy (15:47) ● Health Savings Accounts Benefits (20:05) ● Sequence of Return Risk Discussion (24:09) ● Finding the Right Financial Advisor (30:50) ● Stephanie and Kevin's Wrap Up (39:13) 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. stephanie@sofiafinancial.com You can find the transcript and more information about this episode at www.takebackretirement.com. Follow Stephanie on Twitter, Facebook, YouTube and LinkedIn. Follow Kevin on Twitter, Facebook, YouTube and LinkedIn.
00:00:41
Sep 30, 2025
“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. stephanie@sofiafinancial.com You can find the transcript and more information about this episode at www.takebackretirement.com. Follow Stephanie on Twitter, Facebook, YouTube and LinkedIn. Follow Kevin on Twitter, Facebook, YouTube and LinkedIn.
00:00:41
Sep 15, 2025
“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. stephanie@sofiafinancial.com You can find the transcript and more information about this episode at www.takebackretirement.com. Follow Stephanie on Twitter, Facebook, YouTube and LinkedIn. Follow Kevin on Twitter, Facebook, YouTube and LinkedIn.
00:00:31
Aug 29, 2025
“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. stephanie@sofiafinancial.com You can find the transcript and more information about this episode at www.takebackretirement.com. Follow Stephanie on Twitter, Facebook, YouTube and LinkedIn. Follow Kevin on Twitter, Facebook, YouTube and LinkedIn.
00:00:41
Aug 15, 2025
"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. stephanie@sofiafinancial.com You can find the transcript and more information about this episode at www.takebackretirement.com. Follow Stephanie on Twitter, Facebook, YouTube and LinkedIn. Follow Kevin on Twitter, Facebook, YouTube and LinkedIn.
00:00:42
Jul 31, 2025
“‘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, Paula offers a unique blend of guided writing, storytelling, and actionable tools to help people process grief on their own timeline. She urges those within a widow or widower’s circle to move beyond clichés like “let me know if you need anything.” Instead, she offers specific, compassionate actions—from hanging Christmas lights to making a weekly check-in call. Paula also explains the dangers of isolation, the risks of financial exploitation, and how a personal touch in your condolences can go a long way. She reminds us, above all, that grief manifests differently for each and every person. And so, dealing with it requires a great deal of tact and empathy. “Show up,” she says. “Be Present.” Ask gentle questions. And never underestimate the healing power of presence, story, and a handwritten note. Key Topics · Why Casseroles and Flowers Aren’t Enough (05:15) · Better Ways to Show Up for a Grieving Friend (06:59) · How Grief Evolves Over Time (20:38) · “Don’t Be a Purse”: Financial Boundaries for Widows (21:38) · The Power of Handwritten Notes and Storytelling (28:42) · How Advisors Can Ethically Support the Bereaved (35:27) · Stephanie and Kevin’s Wrap Up (39:25) Resources: · WHCornerstone.com · Paula Harris’ Ted Talk · Wisdom Wednesday with Paula Harris (YouTube Channel) 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. Follow Stephanie on Twitter, Facebook, YouTube and LinkedIn. Follow Kevin on Twitter, Facebook, YouTube and LinkedIn.
00:00:44
Jul 15, 2025
“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. But her real insight lies in making change sustainable through what she calls the “self-perpetuating circle of purpose”: small, habit-based practices in three categories—Body Work, Brain Work, and World Work. Drawing on research from Blue Zones and longevity science, she outlines a holistic strategy grounded in baby steps, accountability, and environment. Whether it’s putting fruit at eye level in the fridge or walking with a group of friends every (or nearly every) morning, Allison makes the case that aging well isn’t about an overhaul, but intention. Allison’s ultimate goal is to help us reimagine our next chapter—not as a slow fade, but as a season of vitality, purpose, and community. Key Topics: Allison’s Turning Point at age 60 (03:12) The Power of Saying Yes and the Misogi Method (05:42) Completing 75 Hard and the Role of Community (07:37) Introducing the Body/Brain/World Framework (15:34) Blue Zones, Longevity, and Daily Habits (17:21) How Environment Shapes Behavior (20:07) The Power of Baby Steps and Planning (21:36) Optimism, Accountability, and Positive Aging (29:48) Key Takeaways (35:25) Resources: Sixty Is a Good Start: A Powerful Body, A Purposeful Life, and a Plan to Make It Happen (book) Allison McCune Davis Website + Link to the 60-Day Dare 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. Follow Stephanie on Twitter, Facebook, YouTube and LinkedIn. Follow Kevin on Twitter, Facebook, YouTube and LinkedIn.
00:00:41
Jun 30, 2025
“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 the belief of being “bad with money,” the influence of childhood messages, and the emotional burden of debt. She advocates for intentionality, self-awareness, and sustainability over perfection, as well as financial journaling and identifying emotional triggers to help people rewrite their “money stories” and build healthier, more resilient habits. “Nothing's going to work for you if it’s not sustainable.” Healing your relationship with money begins with something as small as a $10 weekly savings goal. It’s totally unhelpful to label yourself as “good” or “bad” with money. Personal finance is a deeply personal journey that benefits from reflection, not just spreadsheets. Whether you're confronting debt, struggling with avoidance, or simply seeking a more peaceful relationship with money, give yourself permission to start exactly where you are—with grace. Key Topics: Wendy’s Financial Therapy Framework (03:20) Avoidance and Emotional Burdens (08:39) The “Bad with Money” Myth (10:45) Algorithmic Influences on Money Shame (13:22) Debt, Shame, and Sustainability (15:10) Money as a Tool, Not a Goal (31:28) Where to Begin: Curiosity, Not Judgment (34:14) Resources: WendyWrightFinancialTherapy.com 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. Follow Stephanie on Twitter, Facebook, YouTube and LinkedIn. Follow Kevin on Twitter, Facebook, YouTube and LinkedIn.
00:00:41
Jun 17, 2025
“Usually, people are not trying to kill you or keep you alive for nefarious reasons, unless you're very old and very rich and very mean.” -Patricia De Fonte When most people think of estate planning, they imagine dividing assets among children or a spouse—but Patricia De Fonte, founder of De Fonte Law, offers a broader and deeper perspective. Our hosts, Stephanie McCullough and Kevin Gaines, sit down with Patricia to explore what “estate planning with heart” really means, especially for those without children or partners. People often name child-free individuals as caretakers without their consent, adding invisible burdens. To anybody in this situation, Patricia urges taking ownership: ask questions, know what’s expected, and ensure fair compensation. Far from dry legal jargon, Patricia’s approach to estate planning is a refreshing blending of emotional realism with practical wisdom. The stories she shares—from hospital disputes to posthumous family rifts—tell us just how crucial it is to name the right people, update our documents, and make our values explicit. She encourages everyone to assemble a personal and professional support team, use tools like detailed healthcare directives, and even consider gifts for healthcare proxies as acts of compassion. Plan not just for assets, but for relationships and peace of mind. Key Topics: Patricia’s Philosophy on Estate Planning (03:38) Burden of the Unasked Role (05:11) The Dangers of Safe Deposit Boxes (07:04) Healthcare Directives and Family Conflict (08:59) The Reality of Fiduciary Roles (15:17) “What do You Mean by Liability?” (32:33) Updating Documents and Avoiding DIY Pitfalls (39:16) Stephanie and Kevin’s Wrap-Up (49:43) Resources: DeFonteLaw.com De Fonte Law on YouTube 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. Follow Stephanie on Twitter, Facebook, YouTube and LinkedIn. Follow Kevin on Twitter, Facebook, YouTube and LinkedIn.
00:00:54
Jun 15, 2025
“Usually, people are not trying to kill you or keep you alive for nefarious reasons, unless you're very old and very rich and very mean.” -Patricia De Fonte When most people think of estate planning, they imagine dividing assets among children or a spouse—but Patricia De Fonte, founder of De Fonte Law, offers a broader and deeper perspective. Our hosts, Stephanie McCullough and Kevin Gaines, sit down with Patricia to explore what “estate planning with heart” really means, especially for those without children or partners. People often name child-free individuals as caretakers without their consent, adding invisible burdens. To anybody in this situation, Patricia urges taking ownership: ask questions, know what’s expected, and ensure fair compensation. Far from dry legal jargon, Patricia’s approach to estate planning is a refreshing blending of emotional realism with practical wisdom. The stories she shares—from hospital disputes to posthumous family rifts—tell us just how crucial it is to name the right people, update our documents, and make our values explicit. She encourages everyone to assemble a personal and professional support team, use tools like detailed healthcare directives, and even consider gifts for healthcare proxies as acts of compassion. Plan not just for assets, but for relationships and peace of mind. Key Topics: Patricia’s Philosophy on Estate Planning (03:38) Burden of the Unasked Role (05:11) The Dangers of Safe Deposit Boxes (07:04) Healthcare Directives and Family Conflict (08:59) The Reality of Fiduciary Roles (15:17) “What do You Mean by Liability?” (32:33) Updating Documents and Avoiding DIY Pitfalls (39:16) Stephanie and Kevin’s Wrap-Up (49:43) Resources: DeFonteLaw.com De Fonte Law on YouTube 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. Follow Stephanie on Twitter, Facebook, YouTube and LinkedIn. Follow Kevin on Twitter, Facebook, YouTube and LinkedIn.
00:00:54
May 30, 2025
“Do your research. Do your planning yourself until you get that confidence to project it to the world, and whatever they say will bounce off your armor because you know you’re doing the right thing.” -Shannon Russell Thinking about trading your day job for a business of your own? You’re not alone—and you’re not crazy. Our hosts, Stephanie McCullough and Kevin Gaines, talk with Shannon Russell, a career transition coach who specializes in helping women reinvent themselves through entrepreneurship. Shannon shares her journey from TV producer to franchise owner to business coach, along with insights from her new book, Start Your Second Act. They dive into everything from identifying whether your passion project can really become a business to managing financial risks, exploring different business models, and handling the emotional side of career reinvention. Shannon emphasizes the importance of doing your homework—researching the market, testing ideas on a small scale, and being honest about your needs and goals. Whether you’re chasing flexibility, meaning, or a new income stream in your second act, Shannon’s here to offer your encouragement and practical advice for building something that truly fits your next chapter! Key Topics: Shannon Russell’s Story (02:56) Hobby vs Business (05:39) “If It Were a Job, I Wouldn’t Enjoy It As Much” (10:43) “It’s Not Gonna Be an Overnight Success” (16:10) Adding Extra Streams of Revenue (20:31) The Importance of Having a Mentor or Accountability Group (24:35) About Shannon’s Upcoming Book (31:32) What Shannon Would Do Differently in Business (33:19) Overcoming Potential Identity Crises When Entering Your Second Act (36:36) Getting Clear On Your “Why” (41:58) Takeaways (43:48) Resources: Shannon’s new book: Start Your Second Act Second Act Success Second Act Success 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. stephanie@sofiafinancial.com You can find the transcript and more information about this episode at www.takebackretirement.com. Follow Stephanie on Twitter, Facebook, YouTube and LinkedIn. Follow Kevin on Twitter, Facebook, YouTube and LinkedIn.
00:00:46
May 15, 2025
“We’re talking about giving space to practice. Not only practice the relationships but also practice managing money.” -Sean Maher Most people plan their estate down to the last dollar, but forget to prepare for the emotional fallout that almost always comes from a lack of proper communication between family members. Our hosts, Stephanie McCullough and Kevin Gaines, sit down with husband and wife team Sean and Jill Maher to talk about their book The Greatest Gift: 9 Principles for the Transfer of Your Legacy Along with Your Wealth, which journeys into the emotional side of passing down wealth and family legacy. The idea for the book came after Sean, a financial advisor, saw a well-planned inheritance fall apart when a family started fighting after their parents passed. He brought the issue home to Jill, a mental health counselor, who pointed out that what he was really seeing wasn’t a planning problem—it was grief. Together, they’ve come up with nine key principles that help families avoid drama and stay connected regarding inheritance. The big takeaway? It’s not just about the money. No matter how much (or little) you're passing on, what matters most is communication, shared values, and emotional safety. Jill and Sean suggest families start having small, low-pressure meetings early, while everyone’s still around to talk things through. It’s about creating space for honest conversations, building trust, and setting expectations. Their advice blends practical planning with emotional wisdom, encouraging people to treat legacy as a relationship, not just a transaction. At the heart of it all, their message is simple: don’t avoid the tough conversations—have them, and carry them out with love. Key Topics: Why Sean and Jill Wrote The Greatest Gift (00:49) “You’re Passing on Not Just Money, But Also Legacy” (04:33) How to Set Up and Facilitate the Inheritance Conversation with a Family (10:22) Setting Expectations Upfront to Nip Objections in the Bud (21:07) Why Sharing Your Story is So Critical (28:52) Nurturing Independence (35:53) Creating a Safe Environment for Your Children (45:49) Resources: The Greatest Gift Book USE COUPON CODE: takebackretirement for $5 off and free shipping! 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. Follow Stephanie on Twitter, Facebook, YouTube and LinkedIn. Follow Kevin on Twitter, Facebook, YouTube and LinkedIn.
00:00:51
Apr 30, 2025
"In a blended family, fairness and mutual understanding are key, especially when navigating the complexities of prenuptial and postnuptial agreements.” -Donna Kendrick Navigating love after loss or divorce comes with a host of emotional and financial complexities, especially when blending families. Our hosts, Stephanie McCullough and Kevin Gaines, speak with Donna Kendrick, a financial planner who has lived through these transitions herself. After losing her husband unexpectedly, Donna rebuilt her life and career with a mission to help families in flux—widows, divorcées, and newly blended households. She shares how combining lives means combining financial baggage too, from income disparities and home equity dilemmas to prenups, life insurance, and estate planning. Donna’s candid story highlights the power of transparency and empathy in financial conversations, especially when trust has been tested. Her advice? Begin with individual clarity—define your needs, wants, and non-negotiables—then collaborate with your partner. Donna emphasizes the importance of communication, fairness, and ongoing adjustment as life evolves. Her blend of financial savvy and emotional wisdom offers a powerful reminder: managing money in remarriage is less about spreadsheets and more about mutual understanding. Key Topics: Donna Kendrick’s Story (00:00) Reprioritizing Your Beneficiaries in a Blended Family (12:30) Why Donna Decided to Remarry (16:01) Letting Your Kids Know About Their Future Financial Realities (21:16) Factors When Considering Remarriage (27:28) What Donna Did Wrong During the Process (and What She Did Right) (32:18) Key Takeaways (37:31) Resources: Connect with Donna Widow, Wisdom & Wealth Podcast Take Back Retirement Ep 109: Remarriage & Money: Janice Guinn Joins the Conversation on Love, Legalities, and Life Planning 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. Follow Stephanie on Twitter, Facebook, YouTube and LinkedIn. Follow Kevin on Twitter, Facebook, YouTube and LinkedIn.
00:00:42
Apr 16, 2025
Our hosts Stephanie McCullough and Kevin Gaines sit down with Steve and Jill Marshall of Silver Path Consulting to discuss all things future care, from housing, to finance, to family support. Jill and Steve lament the current lack of societal preparedness for a growing senior population, often referred to as a “silver tsunami” that’s growing bigger each year. They stress the importance of starting early discussions about aging within families, the benefits and drawbacks of different living arrangements, and an effective way to handle comprehensive information and resource management between the adult children of aging parents. The Marshalls also discuss essential legal documents like wills, durable power of attorney, and healthcare power of attorney. Drawing from the recent tragic situation around the passing of Gene Hackman and his wife, they also discuss some technological solutions that adult children can use to facilitate elder care and the value of expert consultation to provide neutral, third-party advice that can ease family tensions. Key Topics: Preparing for the Silver Tsunami (04:47) How to Talk About Future Living Arrangements with Your Aging Parents (10:39) Discussing the Costs of Future Care (17:00) Role Modeling to Your Children the Right Way to Prepare for Future Care (23:07) What Most People Overlook (28:06) Ensuring Everyone in the Family Has a Role (32:30) The Gene Hackman Case (38:53) Steps You Can Take Today to Secure Your Aging Parents’ Future (45:12) Resources: Silver Path Consulting Take Back Retirement Ep. 74: Taking Charge: Carol Marak’s Strategy for Solo Aging and Retirement Planning Take Back Retirement Ep. 83: Combatting Fraud and Protecting Your Financial Future with AARP’s Kathy Stokes 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. Follow Stephanie on Twitter, Facebook, YouTube and LinkedIn. Follow Kevin on Twitter, Facebook, YouTube and LinkedIn.
00:00:54
