Healthcare executive turned writer on “becoming you” after a stroke

The Calm Traveler on layoffs, reinvention, and planning trips differently

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. This episode is about more than travel. It's about what happens when the life you built for decades gets pulled out from under you, and you finally decide to bet on yourself. In this episode, Harold and I discuss: * How surviving 9/11 permanently changed his relationship with time, risk, and what actually matters * Getting laid off via Zoom alongside 4,000 colleagues and feeling an unexpected sense of calm * Why he went back to college in his 50s while working full time * The philosophy behind The Calm Traveler * Why your packed itinerary is the reason you need a vacation from your vacation * How he grew an audience by telling the truth instead of doing what he thought creators were supposed to do * Why betting on yourself gets a lot easier when you stop waiting for family and friends to be your biggest fans Chapters (00:00) Introducing: The Calm Traveler (07:01) Lessons from 9/11 (14:19) The Zoom call that ended it all (21:56) Betting on himself and finding a new path (26:41) The philosophy behind The Calm Traveler (31:54) Why we ruin trips with overpacked itineraries (34:15) Who The Calm Traveler is really for (39:01) The loneliness of entrepreneurship (42:46) The emotional aspect of travel (48:03) YouTube vs. Substack: Finding your voice (54:30) The learning journey: Fordham to ElevenLabs (01:01:32) The best thing that ever happened to him (01:07:31) Building a unique perspective in spite of fear Where to find Harold * Website: https://thecalmtraveler.com/ [https://thecalmtraveler.com/] * Substack: https://thecalmtraveler.substack.com [https://thecalmtraveler.substack.com] * YouTube: https://www.youtube.com/@TheCalmTravelerGuide [https://www.youtube.com/@TheCalmTravelerGuide] For more from The Unemployment Diaries * Stay up to date on Instagram [https://www.instagram.com/theunemploymentdiariespodcast/] * Go behind the scenes on Substack [https://aishaommaya.substack.com/?utm_campaign=profile_chips] * Watch on YouTube [https://www.youtube.com/@theunemploymentdiariespodcast]

Comedian-actor-strategist on finding your voice and using it

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 is redefining success not by what he's gaining, but by what he's refusing to become again. In this conversation we discuss: * Dropping out 7 classes short to build one of the first web companies * What panic-applying after a layoff actually feels like and why he stopped waiting to be picked * Why comedian + actor + content strategist just makes sense * The content mistake most brands make and the 70% open rate that proves there's a better way * His architectural approach to content development * What he was tolerating in corporate that he couldn't name until he left * Success by subtraction: becoming more you by refusing to be anything else * Why he almost turned this podcast down and what that says about how we measure ourselves Chapters (00:00) Introducing: Will Thomas (01:07) How comedian-actor-strategist answers "what do you do?" (05:59) The bold decision to drop out of college (11:50) Finding discipline in a crazy commute (15:10) From corporate to creative freedom (21:03) What Will was tolerating  (25:54) The importance of support systems (27:16) Architectural approach to content creation (29:41) Emotional intelligence in content creation (32:07) Leveraging humor and unique perspectives (35:47) Building a personal brand (39:14) Defining success on your own terms (45:54) Authenticity over comparison Where to find Will  * Newsletter: https://www.williamathomas.com/sunday-setup [https://www.williamathomas.com/sunday-setup] * LinkedIn: https://www.linkedin.com/in/williamathomas/ [https://www.linkedin.com/in/williamathomas/] * Website: https://www.5thhouseleo.com/ [https://www.5thhouseleo.com/] For more from The Unemployment Diaries * Stay up to date on Instagram [https://www.instagram.com/theunemploymentdiariespodcast/] * Go behind the scenes on Substack [https://aishaommaya.substack.com/?utm_campaign=profile_chips] * Watch on YouTube [https://www.youtube.com/@theunemploymentdiariespodcast]

Pro-athlete turned writer on taking her skills off the court

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. Now she's helping others do the same, building a framework for people with multiple interests and not enough direction. In this episode, we chat about: * How growing up in an elite athletic program shaped the discipline that still drives her today * The financial reality of women's sports that pushed her toward a corporate career * How writing became her coping mechanism through grief, identity loss, and coming out to her family * The "restart cycle" of side hustles that never stuck — and what finally did * How she manages her passion while working full-time * Her mental breakdown in 2024, moving back in with her mom at 31, and the moment she got sick enough of her own attitude to change * The Integrator Model: her framework for helping people with multiple interests find one direction that holds them all * The insight she’d give herself about generational impact  Chapters (00:00) Introducing: Jessica (Jess) Almeida (00:50) Jess, the pro basketball player (06:21 ) Jess, the side hustle queen (08:21) Jess, the writer (10:20) Comparing writing and basketball (13:58) The myth of the overnight success (15:57) Being disciplined about your passion (18:15) The power of writing as a tool (20:29) Why Jess stopped complaining (26:08) Managing time and creative energy (26:57) The integrator model (31:22) Having generational impact Where to find Jess  * The Integrator Model [https://jessdanara.com/freetool] * The JD Letter on Substack [https://thejessdanara.substack.com/] For more from The Unemployment Diaries * Stay up to date on Instagram [https://www.instagram.com/theunemploymentdiariespodcast/] * Go behind the scenes on Substack [https://aishaommaya.substack.com/?utm_campaign=profile_chips] * Watch on YouTube [https://www.youtube.com/@theunemploymentdiariespodcast]

CEO of MindHug on why you can’t think your way to change

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. With what behavior is really signaling. With why knowing better almost never leads to doing better. Raj went from central banking to neuroscience research to founding MindHug, a company helping individuals and institutions get unstuck — not through mindset hacks or motivation, but by starting where most approaches never begin: the nervous system. In this episode, Raj shares his story and: * Why the breakdown was years in the making and what signals he wishes he'd paid attention to sooner * The difference between actual threat and perceived threat — and why your mind can't always tell them apart * What dopamine, neural pathways, and epigenetics have to do with your worst habits * The SURE model and why psychological safety is the non-negotiable first step to any real change * How MindHug uses VR, breathwork, and sound to help people experience (not just understand) new ways of being * Why building a new habit beats trying to quit an old one every time * What he'd tell himself before the night everything came crashing down Chapters (00:00) Introducing: Raj Singh (02:06) From autopilot to breakdown (03:59) From Bank of England to MindHug (07:27) Why info alone isn't enough to change behavior (08:04) How the mind gets hijacked (11:36) Innovative approaches to psychological safety (14:32) The role of tech and AI in behavior change (19:01) AI vs human readiness (20:50) The SURE model: Safety, Understanding, Reframing, Experience (26:08) Our reactions are pre-programmed (34:33) Like bio-hacking, but psycho-hacking (36:31) Perception and reality: The illusion of life (38:55) Reading your own signals (42:05) Case Study: Addressing phone addiction (46:53) Don't break old habits — build new ones (51:58) Advice before the breakdown Where to find MindHug * https://mindhug.com/ [https://mindhug.com/] * https://www.instagram.com/mymindhug/ [https://www.instagram.com/mymindhug/] Where to find Raj * https://www.instagram.com/rajmindhug/ [https://www.instagram.com/rajmindhug/] * https://www.linkedin.com/in/chitraj-raj-singh-583b46b/ [https://www.linkedin.com/in/chitraj-raj-singh-583b46b/] For more from The Unemployment Diaries * Stay up to date on Instagram [https://www.instagram.com/theunemploymentdiariespodcast/] * Go behind the scenes on Substack [https://aishaommaya.substack.com/?utm_campaign=profile_chips] * Watch on YouTube [https://www.youtube.com/@theunemploymentdiariespodcast]

Learning expert on the skill no one taught you

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, experiential learning designer, and facilitator who has worked with C-suite leaders, Formula One teams, and UN agencies on the science of how people actually learn. So what changed? Turns out, she didn't hate learning at all. In this episode, Romy shares her story and: * How her environment shaped her relationship with learning (and why her ADHD wasn’t the problem) * Why most training doesn't work and the science behind about how we learn * David Kolb's four-stage learning cycle * The way we unlearn — and why upgrading your software beats wiping the operating system * How learning style preferences can become a trap  * Why psychological safety is a precondition for any real growth * What AI is doing to our critical thinking skills (and what to do about it) * How to design your own learning process * Why we should aim to be explorers rather than experts Chapters 00:00 Welcome, Romy Alexandra 01:18 Are you good or bad at learning? 03:05 From fixed mindset to learning advocate 05:57 Experiential learning: A new approach 07:30 Why knowledge transfer isn't enough 12:03 The shift from education to learning 14:12 What we get wrong about learning 17:53 How to unlearn 21:00 Learning as a lifelong journey 22:58 We learn how we live 27:24 Understanding learning preferences 32:31 Navigating AI in learning 35:44 The importance of critical thinking 38:32 Balancing objectives and learning outcomes 40:19 Designing your own learning process 44:27 Measuring progress in learning 48:18 Creating safe learning environments 53:55 Shifting from expert to explorer mindset Where to find Romy * LinkedIn [https://www.linkedin.com/in/romy-alexandra/] * Website [https://brainmattersconsulting.com/] * Instagram [https://www.instagram.com/trainingbyromy] For more from The Unemployment Diaries * Stay up to date on Instagram [https://www.instagram.com/theunemploymentdiariespodcast/] * Go behind the scenes on Substack [https://aishaommaya.substack.com/?utm_campaign=profile_chips] * Watch on YouTube [https://www.youtube.com/@theunemploymentdiariespodcast]