In Part 3, Waverly Deutsch steps into her latest role: founder of Wyseheart, a coaching firm designed to help the most overlooked founders build ventures that last. Focused on meaningful business, not unicorn exits, she brings her full career of coaching, teaching, and hard-won insight to early-stage leaders across age, gender, race, and identity. For Gen Xers who aren’t ready to “retire,” this is a playbook for doing your best work—on your terms, with your values, and no need for external appro...
May 02, 2025•30 min•Ep. 337
In Part 2, Waverly Deutsch opens up about her decades at Chicago Booth, where she helped founders refine not just their business models but their ability to lead. She discusses how emotional connection strengthens logic, why confident delivery isn’t enough, and how AI is changing but not replacing human insight. For Gen Xers mentoring across generations or rethinking their own leadership, this episode is a reminder: great guidance begins with deep listening. >>Coaching Across the Confidenc...
May 01, 2025•37 min•Ep. 336
We meet Waverly Deutsch not as a Chicago Booth professor or coach for entrepreneurs, but as a real human navigating career decisions in a world that often asks us to pick between passion and practicality. From falling in love with theater to entering computer science as one of only three women in a class of 30, Waverly’s story is one of blending head and heart across every career twist. She shares the real story behind leaving academia for Forrester Research, breaking down in a meeting and still...
May 01, 2025•43 min•Ep. 335
Dominic Carter, CEO of the Carter Group, shares how a personal frustration with his aging parents’ care became a long-term mission: building real, user-driven aging tech in one of the world’s oldest—and most demanding—markets. From human-centric research to venture studio development, Dominic shows how Gen Xers can lead the future of aging by solving the problems we’re all going to face. This isn’t just eldercare innovation—it’s preemptive, practical system design. For those over 50 building wha...
May 01, 2025•33 min•Ep. 334
Dominic Carter, the CEO of the Carter Group, didn’t become an aging tech founder by chasing trends—he got there by building slowly, listening deeply, and surviving the kind of early burnout that forces reinvention. In Part 1, he shares how moving to Japan, launching businesses, and failing hard shaped the systems-thinking approach that now powers his work on aging innovation. This isn’t a startup story—it’s a Gen X blueprint: steady, lived, built from purpose long before it had a name. >>L...
Apr 30, 2025•29 min•Ep. 333
This episode offers you $79 worth of value—completely free. Read till the end for the gift. In Part 2, Kevin introduces the core ideas behind his latest book, Flexible Leadership . He explains why leading isn’t about finding the perfect style—it’s about flexing based on the situation without abandoning your principles. We break down how intention, context, and flexors all work together, why rigid leadership labels backfire, and why the best leaders never stop adjusting how they show up. Key High...
Apr 30, 2025•33 min•Ep. 332
Kevin Eikenberry didn’t start in a leadership lab—he started on a farm where animals had to be fed no matter what else was happening. In Part 1, he shares how early lessons in discipline and systems thinking carried into his leadership work decades later. From his unexpected pivot from fertilizer sales to corporate training, to founding the Kevin Eikenberry Group, Kevin talks about the mistakes, pivots, and realities that shaped his approach to helping others lead better. Key Highlights of Our I...
Apr 29, 2025•26 min•Ep. 331
In Part 2 of his conversation, Tokyo-based American Gary Bremermann moves beyond his own story to share the frameworks and realities that shape career reinvention today. From his Seven Steps to Career Clarity to his candid views on Japan’s ageist hiring market, Gary offers a Gen X blueprint for change: slow, thoughtful, grounded in values, and fiercely human. For anyone tired of chasing titles and ready to build a career worth living on their own terms, this episode delivers both the hard truths...
Apr 29, 2025•24 min•Ep. 330
Tokyo-based American Gary Bremermann didn’t stumble into career clarity—he fought for it across countries, careers, and crises. From hitchhiking North America to building and burning out of his first company, Gary’s story is a blueprint for real Gen X reinvention: practical, nonlinear, and painfully honest. In this first of a two-part series, he shares how early travel, entrepreneurial scars, and the brutal experience of misaligned success shaped the recruiter and career coach he is today. For G...
Apr 29, 2025•31 min•Ep. 329
In the second half of his conversation, Collin Plume moves beyond financial products into financial legacy—sharing how Gen Xers can teach resilience, ownership, and critical thinking to the next generation. From diversifying income streams to protecting family futures with real assets, Collin reveals why wealth isn’t about a flashy portfolio—it’s about building something that lasts, even when systems shift. For Gen Xers tired of flashy advice and ready to raise wiser, stronger humans, this episo...
Apr 27, 2025•37 min•Ep. 328
Collin Plume didn’t build Noble Gold to chase hype—he built it to restore trust in a system Gen X knows can break. In this first of a two-part series, Collin shares how early lessons from insurance sales, real estate, and recession-era survival shaped his people-first approach to wealth building. He explains why real assets like gold and silver aren’t just investments—they’re anchors of ownership in a world increasingly built on debt and paper. For Gen Xers who value resilience over rhetoric, an...
Apr 27, 2025•33 min•Ep. 327
In Part 2 of her conversation, Nina Sossamon-Pogue moves from storytelling to strategy—offering real-world tools for navigating change, resilience, and reinvention. From building a reverse resume to mapping your own success timeline, she shares frameworks that help Gen Xers (and anyone feeling stuck) turn lived experience into a launchpad. Instead of chasing corporate validation or viral moments, Nina reminds us that real success is slow-built, self-defined, and deeply human. For those designing...
Apr 27, 2025•21 min•Ep. 326
Nina Sossamon-Pogue didn’t build a personal brand around change—she built a life out of it. In this first of a two-part series, she shares how elite gymnastics hardwired her resilience, how journalism sharpened her communication instincts, and how a strategic leap into tech proved that reinvention is less about following trends—and more about knowing who you are at the core. For Gen Xers who’ve quietly navigated identity loss, layoffs, industry shifts, and market crashes, Nina’s story is a maste...
Apr 26, 2025•28 min•Ep. 325
In Part 2 of her conversation, Erica Sosna bridges personal resilience and professional wisdom—sharing how The Career Equation helps both individuals and organizations build careers that actually fit. Instead of offering empty advice, Erica gives a practical, human-centered model that empowers people to align their skills, passions, impact, and environment into a sustainable career path. For Gen Xers tired of ad-hoc career advice and vague empowerment slogans, this episode offers a grounded, act...
Apr 26, 2025•20 min•Ep. 324
Erica Sosna was already a respected career strategist, author of The Career Equation , and founder of a successful consultancy. But when a near-fatal accident left her paralyzed in 2022, everything changed. In this first of a two-part series, Erica shares how she rebuilt her life—and her career—on new terms. From learning to walk again to rethinking the purpose of work itself, she offers a blueprint for reinvention that doesn’t rely on hype or hashtags. For Gen Xers who know real change isn’t a ...
Apr 26, 2025•26 min•Ep. 323
In Part 2, Adaira shares how she and Resa shaped Micro Skills into a fast-impact, high-utility guide for early career professionals—and why it intentionally skips fluff in favor of action. She opens up about saying yes too often, burning out from “non-potable work,” and how she finally embraced what she calls JOMO—the joy of missing out. We also hear how they trimmed the book’s original title (“Chisel”) and why ambition without discernment leads to a flat career, not a rising one. Key Highlights...
Apr 25, 2025•19 min•Ep. 322
Dr. Adaira Landry grew up in an under-resourced city, entered Berkeley at 16, and faced early career confusion without access to mentors or professional networks. In Part 1, she shares the formative life moments that led her into emergency medicine—from stepping in to help save a man’s life on campus to surviving a painful burn injury alone. She also reflects on how mentorship found her late, how her master’s in education shaped her communication style, and why she chose to build a practical, in...
Apr 25, 2025•27 min•Ep. 321
In Part 2, Resa explains why she and Adaira started their book MicroSkills with the most overlooked chapter: self-care. From emotional and civic health to better rest and boundaries, she unpacks how showing up well starts before you speak. She also shares practical tools for navigating hard moments—like having a failure buddy—and reveals why thoughtful email etiquette isn’t just about manners, but about professional respect. This episode is about what sustains you—before, during, and after the w...
Apr 24, 2025•29 min•Ep. 320
In Part 1, Dr. Resa Lewiss shares how growing up in Rhode Island, challenging gendered assumptions at home, and studying the liberal arts all shaped her path to medicine. She opens up about the moment emergency medicine clicked for her, and how her love for procedures and working with her hands helped her find her place in a specialty that sees everything, all at once. Key Highlights of Our Interview: Why She Chose Medicine “It was always in me. Nobody in my family was a doctor, but medicine was...
Apr 24, 2025•31 min•Ep. 319
In the second half of their conversation, Edward J. van Luinen, Ed.D. and Tricia Cerrone reveal the system behind their decade-long collaboration—and the framework that became their book, Collaborate to Compete. But this isn’t just theory. It’s a Gen X playbook for how to lead, design, and scale collaboration that actually sticks. Grounded in five core behaviors—generosity, resourcefulness, co-creation, action, and gratitude—and powered by a noble purpose, their method flips the script on outdat...
Apr 23, 2025•35 min•Ep. 318
Edward J. van Luinen, Ed.D. and Tricia Cerrone didn’t build a personal brand around collaboration—they lived one. In this first of a two-part series, they reflect on the working relationship that began at Disney and slowly evolved into a business, a book, and a model for how Gen X builds enduring trust. Forget quick team-building hacks and shallow LinkedIn takes—this is collaboration done the Gen X way: built slowly, refined over time, and grounded in shared values. If you’re tired of performati...
Apr 23, 2025•34 min•Ep. 317
John Gates has been on the inside of more salary negotiations than most of us will see in a lifetime—over 75,000 offers across industries and levels. From a scrappy upbringing in Oregon to global recruiting roles at Capital One and beyond, John learned how the game works. And now, he’s helping jobseekers stop lowballing themselves and start playing smarter. In this episode, he debunks the biggest salary myths, shares the scripts that work, and explains why salary negotiation starts long before t...
Apr 22, 2025•43 min•Ep. 316
Jason Bloomfield didn’t learn change in an MBA program—he learned it through real life. As a teenager, he became the de facto head of household. Now, as Global Head of People Change and Experience Design at Ericsson, he leads transformation across 180 countries. In this episode, Jason shares how active listening, design thinking, and human-first systems have helped him move organizations from dysfunction to alignment. From M&A integrations to HR tech failures, from -83 NPS scores to user-des...
Apr 22, 2025•44 min•Ep. 315
In the second half of her conversation, Erika Ayers Badan—CEO of Food52, former CEO of Barstool Sports, board leader, media powerhouse, and author of _No One Cares About Your Career_—lets us behind the curtain. From negotiating screen time as a kid to rewriting the rules as a high-profile executive, she reflects on how grit, autonomy, and unfiltered curiosity shaped everything—from her parenting to her management style. She shares why she no longer chases titles, what failure really teaches us, ...
Apr 21, 2025•29 min•Ep. 314
Erika Ayers Badan isn’t here to polish the truth—she’s here to say it louder. In this first of a two-part series, the current CEO of Food52 and former CEO of Barstool Sports breaks down the raw realities behind her debut book, No One Cares About Your Career. From writing on commuter trains to fielding hundreds of workplace questions a week, Erika shares why her advice hits different—because it’s honest, hard-earned, and hyper-relevant for a Gen X audience still rewriting the rulebook. This isn’t...
Apr 21, 2025•33 min•Ep. 313
Mark Bayer spent 20 years in the U.S. Congress shaping major policies and managing high-stakes communication for senior lawmakers. In Part Two, Mark gets practical—breaking down the actual tools and mindset shifts PhDs need to thrive in the private sector. From his 11 Keys to Translating Complexity ( complexitymadeclear.com ) to why metaphors matter more than models, he shows how scientists can go from overlooked to unforgettable. Plus, what AI can’t do—and why your human voice still matters mor...
Apr 20, 2025•29 min•Ep. 312
Mark Bayer spent 20 years in the U.S. Congress shaping major policies and managing high-stakes communication for senior lawmakers. In Part One, he reflects on what those years taught him about messaging, persuasion, and why most PhDs—despite their brilliance—struggle to translate their value. From Capitol Hill to Harvard Medical School, Mark now helps scientists and researchers communicate like insiders. This episode is a masterclass in what PhDs get wrong—and what they already have right. Key H...
Apr 20, 2025•29 min•Ep. 311
From facing seven years in prison at 17 to leading soldiers in Afghanistan, Jevon Wooden’s story is more than a redemption arc—it’s about owning your power the moment you realize you’ve still got one. In Part 1, Jevon, the author of "Functional to Phenomenal" and "Own Your Kingdom", opens up about growing up in one of America’s poorest cities, learning to survive, and ultimately discovering his worth had nothing to do with money. Key Highlights of Our Interview: Veterans Day, Forever Changed “I ...
Apr 19, 2025•28 min•Ep. 310
From facing seven years in prison at 17 to leading soldiers in Afghanistan, Jevon Wooden’s story is more than a redemption arc—it’s about owning your power the moment you realize you’ve still got one. In Part 1, Jevon, the author of "Functional to Phenomenal" and "Own Your Kingdom", opens up about growing up in one of America’s poorest cities, learning to survive, and ultimately discovering his worth had nothing to do with money. Key Highlights of Our Interview: The Wrong Crowd, the Right Wake-U...
Apr 19, 2025•26 min•Ep. 309
In Part 3 of this series, narrative strategist Chris Hare leaves us with a gift: the tools to take control of our own stories. Whether it’s envisioning your future in a quiet theater, asking loved ones for feedback through a meaningful 360, or identifying the patterns that shaped your past, Chris’s methods are built for reflection and action. This isn’t productivity advice or LinkedIn bait—it’s practical wisdom for designing a story you can live with. For Gen Xers rethinking legacy, reinvention,...
Apr 18, 2025•24 min•Ep. 308
