The Examined Life

What if the secret to creative freedom isn't making more money but wanting less? Paul Millerd has mastered the art of living well on very little — spending $2,000 a month in Austin, driving a used cars, and now raising his toddler in Thailand. Paul and Khe discuss making creative trade-offs, the toxicity of social media, parenting outside of traditional norms and changing your relationship wit...

I asked AI to roast me. It wasn’t pretty. Then it said, “Do you want me to be meaner?” The exchange was testy and agitating. It then asked, if I want it to go “nuclear.” Is this an AI slippery slope? Who owns our memories? Is creativity at risk? And should we let our kids interact with ChatGPT? [Episode 104] References from the show: • Subscribe to Future-Proof your Career with AI newsletter: http...

Should we be avoiding our uncomfortable emotions? Clinical psychologist, Emily Anhalt explores how we consistently avoid feelings like shame, grief, and sadness through work, substances, or disassociation. Emotional fitness isn't about eliminating these emotions but learning to become comfortable with discomfort. [Episode 103] Dr. Emily Anhalt is a clinical psychologist and author. Learn more...

I left Wall Street 10 years ago. Was it the right decision? What would I have done differently? 10 years is a long time — and comes with a lot of data points to assess the decision. [Episode 102] References from the show: • Walking away from a $2 million salary on Wall Street (with no plan): https://youtu.be/sy4FGaYK_l0 • I Left a $2 Million Job. Here's What I Wish People Had Told Me: https://...

Can you achieve the American Dream by saving half your paycheck? Sam Dogen, founder of Financial Samurai, left Wall Street at 34 with a seven-figure nest egg after a demanding investment banking career. He saved “until it hurts” but would he do it differently? We discuss real estate, generational wealth, and financial freedom. [Episode 101] Sam Dogen is the founder of Financial Samurai, one of the...

What happens when men hit their 40s with all the trappings of success but a gnawing emptiness inside? Greg Scheinman shares his awakening at 47 — the same age his father died — when he realized professional achievement alone wasn't enough. He introduces his "six F's" framework (family, fitness, finance, food, fashion, and fun) as a roadmap for midlife men stuck in the "over-...

What happens when your world shatters with the unimaginable loss of a child? Mary Anne Keegan shares her raw journey after her healthy 20-year-old son Matthew was suddenly diagnosed with cancer and passed away just ten months later. She discovered that grief doesn't follow a playbook — giving yourself grace becomes essential when navigating between holding tight to memories and building a new...

Can capturing untold stories heal decades-old wounds? When Dorothy Chow set up a makeshift podcast studio to record her father's Khmer Rouge survival story, she had no idea what would unfold. What began as a historical preservation project transformed into profound healing for both father and daughter. [Episode 98] Dorothy Chow is the Host of the Death in Cambodia podcast. Learn more about Dor...

To understand today’s market turmoil we need to take a page out of history. This a deep-dive (and front row perspective) on the global financial crisis from 2008. You’ll learn about excess leverage, liquidity crisis, the failure of risk models, and Wall Street impacting Main Street. This will help you decide if you should “do anything.” [Episode 97] JOIN OUR GROUP COACHING COHORTS: Are you looking...

The economy is broken and everything is going to sh*t. That’s the current narrative. But I attended a FIRE (Financial Independence, Retire Early) conference and discovered a thriving community completely defying this narrative. These professionals, not bankers or FANG engineers were nurses, teachers, IT managers. They save aggressively, embrace frugality without suffering, and build very intention...

What happens when career advancement requires you to be manipulative, bossy, and a bit reckless? Jenny Wood's meteoric rise at Google reveals that success often demands breaking unspoken rules. From strategically meeting your boss's boss to mastering the Monday MiniFesto, Jenny shares how walking the line between authentic boldness and calculated self-promotion propelled her career. But be...

Is your identity preventing you from making a necessary change? The golden child, the one who spent decades climbing the corporate ladder, often stays miserable because they can't separate who they are from what they do. Annie Duke reminds us that even the toughest career pivots are surprisingly reversible, and encourages us to imagine what we'd do with those reclaimed 60 hours each week i...

Markets are selling off. Quick, how do you react? I’ve been long (i.e. no selling) since 1999. Yup, 25 years. But that doesn’t mean that major sell-offs don’t test my resolve. It’s particularly hard given our unique financial situation: lots of financial assets, no cash, low income and high spending. So how do we do it? [Episode 93] References from the show: • How to stay calm in a bear market: ht...

What happens when you hit a career crossroads and don't know which path to take? Anne-Laure Le Cunff discusses navigating "liminal spaces" – those uncomfortable in-between periods where you've left something behind something familiar but haven't yet found what's next. Instead of rushing to the nearest known thing or following the obvious sequel to your career, she offers...

What happens when a brain tumor forces you to actually take a break and stop? After decades in management consulting and startups, Steve Mallouk's diagnosis made him confront the difference between chasing "enough" money versus "enough" life experiences. His journey from BCG partner to embracing vulnerability reveals how facing mortality can have unintended consequences. [E...

Is your drive for success killing you? Lou Marchetti was a private equity Master of the Universe until he dropped dead during a CrossFit workout. (Yes, he had a heart attack.) Despite this wake-up call, it took getting fired two years later to finally confront the deeper void his relentless achievement was trying to fill, leading him on a journey from compulsive doing to conscious being. [Episode...

What the heck is happening to the internet? Why does everything feel so different now? Between algorithmic feeds optimizing for outrage, AI-generated content flooding our feeds, and the commodification of our attention, we're watching the entire digital landscape transform in real-time. What does this mean for connection, authenticity and truly expressing our human-ness? [Episode 89] Here'...

Is the 40-hour work week dead? Elle Griffin’s research shows that 70% of salaried workers clock less than 40 hours. But here's the twist: as AI and automation make us more efficient, we're not necessarily working less – we're choosing to create more. From remote software engineers to newsletter writers, the future isn't about less work, it's about having the freedom to choose how we spend our time...

Are solopreneurs destined to be stuck trading time for money? Serial entrepreneur Bart Egnal breaks down the traps of scaling a service business — where more revenue often leads to lower profits and bigger headaches. As entrepreneurs hit different revenue breakpoints, they face crucial decisions about hiring, systematizing their IP, and most importantly, whether scaling aligns with their deeper mo...

What happens when a founder walks away from $60 million after selling his company? Post-achievement entrepreneurs often find themselves chasing bigger highs yet nothing fills the void of being without a rudder. Loom co-founder Vinay Hiramath's candid story reveals a deeper truth about conditional love and validation that many children of immigrants face: the crushing fear of being ordinary [Ep...

What happens when your spouse's startup explodes and you're suddenly worth $20 million? The anonymous spouse of a successful founder shares the real truth about identity earthquakes, unconscious power shifts, and the loneliness of being the "hidden partner" in entrepreneurial marriages. She candidly reveals how couples navigate the psychological whiplash of going from breadwinner to background cha...

What if we've been thinking about retirement planning all wrong? Christine Benz, Morningstar's personal finance expert, breaks down how our obsession with the financial aspects of retirement often overshadows other priorities like relationships and purpose. Drawing from her new book "How to Retire," she challenges the conventional wisdom that you'll spend the same in retirement as during your peak...

If you’re looking to ditch anxiety, overwhelm and comparison — this episode’s for you. Executive coach Joe Hudson put out a list of steps to develop your emotional resilience and Khe reacts to the entire list. I promise you’ll find a handful that resonate. [Episode 83] And if you have a Big Decision to make in 2025 check out Joe Hudson’s Great Decisions course. RadReaders will receive a $300 disco...

Is searching for your life's purpose causing more anxiety than fulfillment? Jordan Grumet, a former doctor turned author and podcaster, discovered that chasing "Big P" purpose – those audacious, society-approved goals – often leads to burnout and emptiness. Instead, he advocates for embracing "Little P" purpose: the small, joy-filled activities that light us up, which paradoxically can create deep...

We would love to live in another country with my kids. But there’s inertia, logistics and — let’s be honest — a baked in view (for Americans) that despite its warts, life is pretty good here. I’m inspired by families who challenge conventions and blow things up a bit — especially if they have kids. Tiago Forte and Lauren Valdez left comfy Southern California for Valle Del Bravo in Mexico. [Episode...