The Examined Life

Khe Hy
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.

  1. MAR 27

    Should you be weird and manipulative at work? [Jenny Wood]

    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 beneath these tactics lies a deeper truth – it's not about becoming cutthroat, but about pushing past the fear of judgment that keeps most people playing small. [Episode 95] Jenny Wood is a former Google Executive, author and entrepreneur. Learn more about Jenny: • Website: https://itsjennywood.com/ • LinkedIn: https://www.linkedin.com/in/jennyilles • X/Twitter: https://x.com/itsjennywood?lang=en • Instagram: https://www.instagram.com/itsjennywood/ —- 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 ⁠⁠⁠⁠⁠🎥 TikTok⁠⁠⁠⁠⁠ Podcast art by Nate Kadlac, photography by Henry Thong

    49 min
  2. MAR 20

    When should you quit? [Annie Duke]

    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 if we finally walked away. [Episode 94] Annie Duke is an Author, Professional Speaker & Decision StrategistLearn more about Annie: • Annie's Website: https://www.annieduke.com/ • LinkedIn: https://www.linkedin.com/in/annie-duke/ • X/Twitter: https://x.com/annieduke?lang=en References from the show: • Your Future Self by Hal Hershfield: https://www.halhershfield.com/yourfutureself • How to Change by Katy Milkman: https://www.katymilkman.com/book • Alliance for Decision Education: https://alliancefordecisioneducation.org/ • The Decision Education Podcast: https://alliancefordecisioneducation.org/podcasts/ —- 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 ⁠⁠⁠⁠⁠🎥 TikTok⁠⁠⁠⁠⁠ Podcast art by Nate Kadlac, photography by Henry Thong

    1h 1m
  3. MAR 6

    How do you navigate career uncertainty? [Anne-Laure Le Cunff]

    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 pragmatic steps to thrive in the uncertainty. [Episode 92] Anne-Laure Le Cunff is a Neuroscientist, Ex-Googler, Founder and Author. Learn more about Anne-Laure: • LinkedIn: https://www.linkedin.com/in/neuranne/?originalSubdomain=uk • X/Twitter: https://x.com/neuranne • Instagram: https://www.instagram.com/neuranne/?hl=en • YouTube: https://www.youtube.com/@neuranne • Tiny Experiments Book: https://nesslabs.com/book —- 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 ⁠⁠⁠⁠⁠🎥 TikTok⁠⁠⁠⁠⁠ Podcast art by Nate Kadlac, photography by Henry Thong

    51 min
  4. FEB 27

    What’s next after a brain tumor? [Steven Mallouk]

    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. [Episode 91] Steven Mallouk is a happily retired executive living life to the fullest. Learn more about Steven: • LinkedIn: https://www.linkedin.com/in/stevemallouk/ References from the show: • My wish this Christmas: More of the gift of life itself.: https://www.linkedin.com/pulse/my-wish-christmas-more-gift-life-itself-steve-mallouk-3hhbc/• My Update, 4 Weeks After Brain Surgery: https://www.linkedin.com/pulse/my-update-4-weeks-after-brain-surgery-steve-mallouk-thszc/—- 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 ⁠⁠⁠⁠⁠🎥 TikTok⁠⁠⁠⁠⁠ Podcast art by Nate Kadlac, photography by Henry Thong

    1h 2m
5
out of 5
106 Ratings

About

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.

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