In Part 2 of his three-part series, narrative strategist Chris Hare shares the stories he used to survive. From a near-suicidal season while working at Amazon to a healing moment years later in a record store, this episode unpacks how internal stories—if left unchecked—can become prisons. But when named, challenged, and re-authored, they can also become paths to freedom. For Gen Xers who’ve spent decades carrying stories they didn’t choose, this is a masterclass in taking your story back—and cho...
Apr 18, 2025•36 min•Ep. 307
In Part 1 of this three-part series, Chris Hare shares how a single founder story sparked a strategy pivot inside Amazon—and why storytelling isn’t fluff, it’s infrastructure. As a behind-the-scenes strategist for some of tech’s biggest companies, Chris has spent decades shaping narratives that align people, purpose, and performance. But his real power lies in his Gen X sensibility: low drama, high pattern recognition, and deep alignment between what’s said and what’s done. This episode explores...
Apr 17, 2025•23 min•Ep. 306
In Part 2 of her conversation, Sara Lobkovich doesn’t just tell us what strategy is—she shows us who it’s for. Her book, You Are a Strategist , is more than a guide to OKRs or goal-setting. It’s a toolkit for people who’ve always felt misaligned, misunderstood, or mislabeled in traditional business environments. Drawing from her own experience as a trauma survivor, neurodivergent thinker, and late-diagnosed ADHD strategist, Sara offers business frameworks that finally include the rest of us. For...
Apr 17, 2025•34 min•Ep. 305
Sara Lobkovich didn’t pivot to be edgy. She adapted because the system never fit—and she refused to shrink herself to match it. In this first of a two-part series, Sara walks us through her nonlinear arc: from teen internet entrepreneur to lawyer, from burnout strategist to behavioral goal-setting expert. Along the way, she reveals how quiet defiance, early activism, and radical self-curiosity helped her rewire how she worked and lived. For Gen Xers tired of being told to “just fit in,” this epi...
Apr 17, 2025•35 min•Ep. 304
In this second half of her story, Holly Bond comes full circle—returning to the recruiting world she once left behind, this time to rebuild it from the ground up. At Facets, she’s proving that scaling a business doesn’t require sacrificing soul. From her pay structure to her candidate experience to her team’s human-first process, Holly is quietly leading a revolution in executive search. She also drops some of the best job-seeking advice on the show to date—especially for Gen Xers navigating rei...
Apr 16, 2025•34 min•Ep. 303
Holly Bond didn’t inherit a business or a playbook—she built her own, from the basement up. In this first of a two-part conversation, she shares how a late return to university, a family health wake-up call, and pure Gen X tenacity drove her to create a kids’ fitness franchise with national impact. Holly’s story is part entrepreneurship, part emotional reckoning, and full of hard-earned wisdom for anyone designing change from the inside out. If you’ve ever thought it was too late, too messy, or ...
Apr 15, 2025•32 min•Ep. 302
In Part Two, Sande takes us into the quieter—but more honest—chapter that followed. He shares what happened when he stepped off the growth treadmill, redefined ambition, and began unlearning the beliefs that kept him over-performing and under-listening. From rebuilding marriage to carving out what he calls Life Peels, Sande shares what it means to grow by subtracting—not stacking. Key Highlights of Our Interview: Life After the Climb “What would happen if I just got really quiet and listened? No...
Apr 15, 2025•42 min•Ep. 301
Sande Golgart was the guy who said yes to every opportunity, outran every challenge, and never sat still—until one day, the success story stopped feeling like his. In Part One, he opens up about going from slam dunk champ to corporate high-performer to someone questioning the very game he was winning. He talks about early ambition, the trap of nonstop action, and the moment he realized: “You climb, climb, climb… then realize the mountain isn’t even yours.” Key Highlights of Our Interview: From S...
Apr 14, 2025•34 min•Ep. 300
Chris Quek isn’t just building startups—he’s building a generation. In this second half of his story, he shares how selling his inheritance became the launchpad for Thrive, a VC firm that invests in Southeast Asia’s overlooked next-gen entrepreneurs. From structuring value-aligned startups to teaching his kids the principles behind technology, Chris shows how legacy isn’t something you receive—it’s something you design . For Gen Xers navigating intergenerational tension, personal ambition, and r...
Apr 14, 2025•33 min•Ep. 299
Chris Quek could’ve stayed in the family business and lived comfortably. Instead, he chose a life of uncomfortable clarity. In this first of a two-part series, Chris shares how he rejected expectations, fled the legacy he was born into, and built an e-commerce business in Malaysia with nothing but grit and guidance from mentors. Now 46, he reflects on what identity really means when you’re not handed a playbook—and how each phase of reinvention brings you closer to your core. For Gen Xers rewrit...
Apr 14, 2025•28 min•Ep. 298
In this second half of his conversation, Gagan Sandhu pulls back the curtain on what it really means to design financial independence. It’s not about the FIRE movement or early retirement—it’s about knowing your trade-offs and making conscious, math-informed decisions that align with your values. From career reinvention every 10 years to balancing ambition with family time, Gagan offers Gen Xers a refreshingly grounded take on money, identity, and midlife work design. >>Financial Independe...
Apr 13, 2025•37 min•Ep. 297
Gagan Sandhu didn’t chase freedom. He calculated it. In this first of a two-part series, the Chicago Booth MBA, former tech exec, and founder of fintech startup Zillion shares how he redefined financial independence—moving beyond buzzwords and into practical action. From his immigrant roots to his pivot from mechanical engineering to Silicon Valley, Gagan shows how knowledge—not speed—builds real freedom. Whether you’re Gen X or Gen Z, this conversation reframes wealth not as a finish line, but ...
Apr 13, 2025•34 min•Ep. 296
What do you do when the person you’ve been—mom, fixer, chauffeur, planner—is no longer needed in the same way? In Part 2, Jodi shares the emotional (and practical) shift from parenting full-time to rediscovering your own interests. She walks us through her signature DARE Method and dishes out real talk on marriage, identity, and why your kids aren’t your best friends (even if you really, really like them). This isn’t just an episode about empty nests. It’s about refilling your own life—on your o...
Apr 13, 2025•25 min•Ep. 295
Jodi Silverman didn’t set out to lead a movement—she just wanted to figure out what came next. In Part 1, she opens up about career shifts, midlife transitions, and how becoming an empty nester sent her on a completely different path. Spoiler: it involved leaving behind a successful print business, embracing a “dare,” and launching a community that now supports thousands of women through their own identity resets. Whether you’re a parent or not, this is a story about transition, reinvention, and...
Apr 12, 2025•22 min•Ep. 294
Wayland Lum has built a leadership career that spans tech giants, global consulting, and top business schools—but his boldest move was walking away from all of it to build something from scratch. Now the founder of Copperbox, he coaches modern leaders through a philosophy that fuses deep psychology, personal courage, and timeless wisdom. In this episode, he shares the moment he chose purpose over prestige, the emotional realities behind true leadership, and why fear and courage are two sides of ...
Apr 12, 2025•26 min•Ep. 293
César Couto Ferreira spent over a decade deep in the world of global media—shaping MTV across Europe and Africa, working with stars, and riding the wave from analog to digital. But when Amy Winehouse died, something broke. Not in the headlines, but inside him. He saw how the industry treated artists as content—not people—and decided he couldn’t be part of it anymore. That moment became his call to redesign his life. In this episode, César shares how he left global prestige behind to build system...
Apr 12, 2025•24 min•Ep. 292
Ryota Tanozaki didn’t pivot because of burnout—he pivoted to avoid a trap. While managing a turnaround project in rural Japan, he saw the writing on the wall: stay too long, and his world would shrink. Instead, he chose to bet on himself. He went global, earned an MBA from Chicago Booth, built a career across Facebook and Tabist (backed by Softbank Japan), and led a hospitality startup through one of the toughest periods in travel history. But his secret wasn’t speed—it was clarity. In this epis...
Apr 11, 2025•33 min•Ep. 291
In Part 2, Lora walks us through the why behind her return to music full-time. From co-founding Virtuoso Fiesta to launching her album Reveries on Ivories , she shares how composition became her storytelling tool—and how she sees music not just as art, but as a way to build peace, shift perspectives, and maybe even fix broken systems. This isn’t a story about following your passion. It’s a story about building the courage to lead with it. >>Reveries on Ivories (New Album) by Lora Chow<&...
Apr 11, 2025•21 min•Ep. 290
You don’t expect a hedge fund manager to also be writing operas. But Lora Chow has always done things differently. In Part 1, she shares how a childhood love of music led her to Yale, how she pivoted from potential math major to economics and music, and how the Hong Kong hustle—and one very lucrative offer—put finance ahead of passion… at least for a while. This episode isn’t about quitting your job on a whim. It’s about trusting the detours that make the next chapter possible. Key Highlights of...
Apr 11, 2025•28 min•Ep. 289
Most change efforts fail because they forget one thing: people. In Part 2, Richard breaks down The Book of Change , his 39-step model for leading transformation without leaving common sense behind. We get into the difference between showing up with a framework vs. showing up ready to listen—and what AI might never understand about real leadership. Key Highlights of Our Interview: What Most Consultants Miss “They deliver a binder and disappear. That’s not help. That’s homework.” Why Richard built...
Apr 10, 2025•25 min•Ep. 288
Richard Carson’s career didn’t unfold by design—it unfolded by curiosity. From planning cities to fixing broken systems, he’s never been afraid to say, “This isn’t working—let’s figure out why.” In Part 1, he shares how a job he hated, a grocery store run, and one very weird time-tracking system helped shape his unconventional path to becoming a change consultant. Key Highlights of Our Interview: From Archaeology to Urban Planning “I thought I wanted to dig things up. Turns out, I just liked sol...
Apr 10, 2025•30 min•Ep. 287
Michael Levitt nearly lost everything to burnout—a heart attack, job loss, foreclosure, and total collapse. But what brought him back wasn’t a digital detox retreat—it was Gen X wisdom: learning to reset without relying on tech. As the founder of the Breakfast Leadership Network and burnout consultant to global execs, Michael now teaches others how to rebuild. In this episode, he explains why recovery starts with sleep, why analog habits like ditching your smartphone alarm matter, and why burnou...
Apr 09, 2025•42 min•Ep. 286
Steve Monaghan flips the script on innovation culture: experience isn’t a relic—it’s a strategic edge. As General Partner at FinMir.ai, Limited Partner at True Global Ventures, Independent Non-Executive Director at RAK Bank, and former Chief Digital Officer at both AIA and DBS Bank, Steve brings a cross-industry view forged through decades of deep transformation. From aviation to fintech to AI, he shows how age fuels better questions, sharper pattern recognition, and global insight in a world ob...
Apr 09, 2025•44 min•Ep. 285
In Part 2 of our conversation, Katie Curry flips the script—from navigating her own reinvention to mentoring the next generation through theirs. As a Gen X leader, she draws from both parenting and management to offer real tools for leading Gen Z with clarity, empathy, and pace. Katie doesn’t romanticize change—she makes it strategic. From book recs to career advice to community wisdom, this episode is a field guide for anyone navigating a multigenerational workplace—and still trying to grow on ...
Apr 09, 2025•25 min•Ep. 284
Katie Curry doesn’t follow a path—she redraws the map. In this first of a two-part conversation, we explore her journey from communist Bulgaria to the heart of Wall Street, from technical risk roles to creative leadership. Katie shares how she builds mental toughness, adapts across industries, and leads Gen Z with humor and humility. Through it all, she reminds us that reinvention isn’t something you do once—it’s a muscle you build. For Gen Xers who know how to change ambitiously, this is reinve...
Apr 08, 2025•22 min•Ep. 283
Forget hot takes and hustle porn—Josh Geballe has built a career on real outcomes, not optics. As a former IBM exec, startup CEO, crisis-tested public leader, and now head of Yale Ventures, he’s navigated every kind of system—and rewired more than a few. In this episode, Josh breaks down what it takes to lead without ego, make career moves without a roadmap, and support innovation without turning it into performance. For Gen Xers designing careers that are built, not branded, this is substance o...
Apr 08, 2025•29 min•Ep. 282
Irina Filippova is not here to perform change—she’s here to live it. From her early career as a Russian diplomat to her current role as COO of a BlackRock-backed energy transition venture, Irina has made a habit of rewriting the rules instead of following them. In this episode, she shares what it really means to be a self-starter in a world obsessed with shortcuts, how real leaders use courage to stay in integrity, and why the most meaningful change begins with inner work. For anyone who’s tired...
Apr 08, 2025•42 min•Ep. 281
This episode dives into Bond , the new book by Greg Morley—former global DEI head at Moët Hennessy and veteran HR leader at Disney and Hasbro. Vince and Greg unpack the emotional undercurrent of modern work—how a broken culture can push people into burnout and how small moments of recognition can pull them back. With global insight and Gen X clarity, Greg shares what real inclusion looks like on the ground, from Asia to Europe to the U.S. If you’re ready to lead with depth, not just diversity me...
Apr 08, 2025•42 min•Ep. 280
Greg Morley isn’t reinventing himself at midlife—he’s been reinventing all along. As a Gen X leader who’s shaped HR and DEI strategy at Disney, Hasbro, and Moët Hennessy, Greg represents the quiet force of a generation that never needed to go viral to make an impact. >>From Complaint Calls to Corporate Change “80% of the calls were complaints. That’s how I learned to listen—fast.” Greg started in the trenches and never forgot what real work feels like. That early frontline experience now s...
Apr 08, 2025•31 min•Ep. 279
So you’ve figured out your career isn’t working—now what? In Part Two, Helen brings in the big guns: her framework for getting unstuck, redesigning with purpose, and navigating the messy middle of change. We unpack the real reasons people stay stuck, why perseverance isn’t always a virtue, and how to redesign a career that fits who you are now—not who you were five years ago. It’s part psychology, part strategy, and 100% relatable. Key Highlights of Our Interview: Three Acts of Career Redesign “...
Apr 06, 2025•28 min•Ep. 278
