
The Examined Life
Here’s a scary fact about adulthood. We stop asking questions. We lose the playful curiosity and creativity that we had as children. And it’s a shame. Questions are gateways to our deepest desires, insecurities and dreams. Reflecting on a deep question takes us one step closer to a life well-lived. Each week, we’ll ponder and debate one of life’s thorniest questions. We’ll explore ambition, careers, money, relationships, productivity and psychology — all in the pursuit of living an Examined Life.
Latest episodes

51 snips
Mar 20, 2025 • 1h 1min
When should you quit? [Annie Duke]
Annie Duke, an author and decision strategist, shares her unique insights from the world of poker to the nuances of decision-making. She discusses how identity can hold us back from making necessary career changes and the psychological traps, like loss aversion, that complicate quitting a job. Duke emphasizes that decisions can often be reversible, encouraging listeners to think about what they could reclaim if they walked away from unfulfilling roles. She also tackles biases and introduces the idea of evaluating opportunity costs for greater fulfillment in life.

7 snips
Mar 13, 2025 • 26min
Is it time to sell? [Khe Hy]
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: https://www.khehy.com/how-to-stay-calm-in-a-bear-market—-JOIN OUR GROUP COACHING COHORTS:Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers)Apply today—-BECOME A RADREADER:📩 Join 50,000+ ambitious professionals for our weekly essays on productivity, money and career.🐦 Twitter📸 Instagram💼 LinkedIn🌍 RadReads Blog🎥 TikTokPodcast art by Nate Kadlac, photography by Henry Thong

28 snips
Mar 6, 2025 • 51min
How do you navigate career uncertainty? [Anne-Laure Le Cunff]
Anne-Laure Le Cunff, a neuroscientist and founder of Nest Labs, dives into the uncharted waters of career uncertainty. She discusses 'liminal spaces' and how to make the most of those awkward in-between phases. Rather than rushing into familiar territory, she advocates for setting smaller goals and conducting 'tiny experiments' to navigate your path. With insights on balancing passion and financial stability, Anne-Laure empowers listeners to confront their fears and embrace personal growth during transitional times.

13 snips
Feb 27, 2025 • 1h 2min
What’s next after a brain tumor? [Steven Mallouk]
Steven Mallouk, a former management consultant turned adventurer, shares his life-altering experience after a brain tumor diagnosis. He discusses the transformative journey from a career-focused mindset to embracing meaningful life experiences. Steven highlights the emotional challenges of facing surgery, the importance of vulnerability, and how his definition of success shifted from material gains to cherished relationships. His story demonstrates the beauty of confronting mortality and the deep connections formed during life’s toughest challenges.

12 snips
Feb 20, 2025 • 1h 14min
What if your job actually kills you? [Lou Marchetti]
Lou Marchetti, a former private equity dealmaker, shares his gripping story after a near-fatal heart attack during a workout. He reveals how this life-altering moment spurred his shift from relentless ambition to a more conscious existence. Lou delves into the emotional turmoil following his job loss, emphasizing the significance of reflection in navigating life’s challenges. He recounts his recovery journey, along with lessons on resilience and the transformative power of self-discovery, ultimately urging listeners to prioritize health and fulfillment over mere success.

19 snips
Feb 13, 2025 • 27min
What the heck happened to the Internet? [Khe Hy]
The podcast dives into the chaotic transformation of the internet, highlighting how social media has shifted to prioritize outrage and controversy. It questions the implications of AI-generated content and its effect on genuine human connection. The discussion also covers the changing role of platforms like Twitter in shaping news and society. Ultimately, it explores the challenge of remaining authentic in a digitally commodified landscape, urging listeners to reflect on their own interactions with technology.

36 snips
Feb 6, 2025 • 1h 3min
Is the 40 hour work week dead? [Elle Griffin]
Elle Griffin, founder of The Elysian media cooperative, discusses the evolving landscape of work as 70% of salaried workers report clocking less than 40 hours a week. With AI and automation enhancing efficiency, people are choosing to create more rather than simply working less. They explore the potential for a 20-hour workweek and the shift in career prestige towards entrepreneurship. Additionally, they delve into the balance of work and leisure, emphasizing the importance of personal passions in this new work paradigm.

14 snips
Jan 30, 2025 • 56min
How do you create leverage as an entrepreneur? [Bart Egnal]
In this insightful discussion, Bart Egnal, a serial entrepreneur and CEO of The Humphrey Group, shares his journey from childhood sales to leading successful businesses. He discusses the traps of scaling service-based industries, highlighting the balance between revenue growth and profitability. Bart emphasizes the importance of effective communication skills for leaders and the necessity of sustainable business models. He reflects on personal fulfillment in entrepreneurship and the evolving coaching landscape, urging aspiring leaders to adapt and maintain their unique styles.

Jan 23, 2025 • 32min
Can Money Buy Happiness? [Khe Hy]
What happens when you walk away from a $60 million payday? Explore the journey of a tech entrepreneur grappling with emptiness post-success. Discover how the search for fulfillment can lead to deeper self-reflection and the struggle to find joy in ordinary moments. Delve into the immigrant experience that shapes perspectives on love and validation. This discussion challenges societal pressures and emphasizes the importance of engaging in activities for personal satisfaction rather than external approval.

Jan 16, 2025 • 57min
What’s it like being married to an entrepreneur? [Anonymous]
Dive into the intriguing dynamics of being married to an entrepreneur, where sudden wealth can lead to identity crises and emotional upheaval. Discover the hidden struggles of partners feeling sidelined as their spouse's success skyrockets. Explore how communication and community support are vital in navigating these challenges. The conversation also touches on the loneliness post-success, the shifting balance of ambition and family values, and the emotional toll entrepreneurship takes on relationships. It's a candid look at love in the face of financial triumph.