The Unemployment Diaries

On this podcast, we talk a lot about the process of becoming unemployed from beliefs and systems that hold you back. But what happens when you know what you want to say, but can’t figure out why you’re not being heard? Before he coached executives to command a room, Michael Hewitt spent a decade commanding rooms himself performing opera without a microphone for audiences of over a thousand people....

What happens when a 9/11 survivor, Navy veteran, and 28-year corporate travel veteran gets laid off on a Zoom call with 4,000 other people ? Harold Wilkerson didn't panic or spiral. He has too much experience with hard things for that. He got quiet, got intentional, and built The Calm Traveler: a Substack and travel consultancy helping people over 50 rethink how they move through the world. Th...

Will is a triple threat: stand-up comedian, actor, and B2B content strategist with a newsletter that gets a 70% open rate. He's also someone who spent years flattening himself to fit inside corporate culture (anyone else resonate?) — and is now methodically peeling every layer back. We talk about what it actually means to build an audience, why human content will always beat AI, and how Will i...

How many people do you know who are actually building the life they want, instead of the one they settled for? Jessica (Jess) Almeida played basketball for Portugal from the age of 13. At 24, she traded the sport for a corporate paycheck — and spent years wondering if she'd made a mistake. Today, she still works full time. But she found writing: same discipline, same obsession, different game....

Change. Whether it's a shift in career, lifestyle, or behavior patterns — we usually know what we need to do differently. So then… why can't we do it? Raj Singh had the career everyone told him to want. LSE economist. Bank of England. Stable, prestigious, on track. And then one night, it fell apart. What followed wasn't just a pivot. It was a reckoning. With how the mind actually works...

Have you ever thought about how you learn? Or, for that matter, why you learn in the first place? Romy attended schools that prided themselves on academic rigor. From the third grade, she was pulling all-nighters and spent years feeling like she was one step behind. She walked out of her final university exam and celebrated never having to learn again. Today, she's a Chief Learning Officer, experi...

Florence Acosta spent years building herself around her credentials of nurse anesthetist and executive director of a surgical center. On the weekends? She was doing work she loved but never fully committed to: facilitating women's circles. Then she had a stroke. And overnight, the career, the title, the independence — all of it — was gone. What followed was two years of sweats, silence, and gr...

What happens when the career you built becomes the thing that breaks you down? Yannick Kpodar spent fifteen years in front-row seats at some of Europe and San Francisco’s fastest-growing companies — LinkedIn, PayFit, and a unicorn valued at $2.2 billion. He raised hundreds of millions as an operator and by every external measure, he was winning. Then, in the span of 6-12 months, he lost his job, h...

What if the worst thing that ever happened to you turned out to be the making of you? Patrick grew up knowing exactly who he was going to be. His grandfather's photo above the fireplace. His dad's. A blank third frame he promised himself he'd fill. He applied to just one school (The Citadel), joined the Marine Corps, and became a platoon commander leading 40 Marines. He was living his...

What if the thing that changed your life wasn't supposed to be your life at all? Maya stumbled into a Brazilian Jiu-jitsu class at 16 thinking it was kickboxing. She then started a business at 19 with $2,000 and kept it secret for two years. Recently, she took it to Shark Tank and walked away with $300,000. But this episode isn't really about any of that. It's about what it takes to be...

What if you already know what you need to but you just won't do it? Jacob Templer went from law school to state attorney to elephant conservation to tech sales to travel content creator. Any one of those would have been a solid career. None of them were the right life. Now he helps people figure out the difference before they waste any more time.  In this episode, Jacob and I discuss: Why bein...

What if the life you always wanted had no map, no guarantee, and no way back? Linda Jackson spent decades in tech sales and marketing, working for startups and surviving volatile bosses. Then she sailed out under the Golden Gate Bridge (just two weeks after 9/11) on a 34-foot sailboat with her husband and a one-year plan that turned into a lifetime. Today they live full-time aboard their sailboat...

What if the trait you've been hiding is actually your greatest asset? Mohamed Fadel spent years behind a computer screen, finding community, purpose, and progression in online gaming. Then, at only 24, he became the Global President of AIESEC, the world's largest youth-led organization, leading 40,000 young people across 120 countries. As a self-proclaimed 97% introvert. He didn't chan...

What if the question "so, what do you do?" is the wrong question entirely? Charlie Rogers never had a conventional answer because he never took the conventional path. He built and closed businesses, represented Great Britain in triathlon, and spent the last decade figuring out how to live beyond labels. Now he's written the field guide for everyone else who's ever felt too much f...

A layoff. A house under construction. A trip to London. And the realization that the life he wanted was within reach.  These moments pushed Tim Akapo to trade a 20-year supply chain career for an espresso machine — and build one of Westchester's most beloved community spaces, Ludy Café, from the ground up. In this episode, Tim shares: How he went from laid off to running a business generating over...

Motherhood. A global pandemic. And the realization that the career she had pursued for so long no longer fit. These major life shifts prompted  Sofía Paredes Chaux to leave the United Nations and step into a new chapter — one centered on helping others reconnect with themselves. In this episode, Sofía shares: Her journey from the UN to becoming a life coach A way to avoid repeating the same emotio...

Whether you’re building a company, navigating a career pivot, dreaming up your next big idea, or just trying to understand the insane pace of technological change, this conversation might change how you think about innovation, creativity, and what’s coming next. Today, we sit down with Chris Kalaboukis — a futurist, technologist, and philosopher known for his work at the intersection of tech fores...