Episode (200)
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Ep. 369: Why Are We Getting Dumber? A Debate.
Sep 08, 2025IQ scores had been steadily rising since WWII. But, more recently, this phenomenon has stopped. Since 2010, we’ve actually been getting dumber. In this episode, Cal gets into the common theories for ...
IN-DEPTH: The Game of Life (w/ Tim Ferriss)
Sep 04, 2025In this episode of IN-DEPTH, Cal is joined by bestselling author and podcaster, Tim Ferriss. Tim rocketed to prominence with his 2007 book, “The Four Hour WorkWeek” which basically redefined a generat...
Ep. 368: I Want Work-Life Balance. Am I Doomed to Mediocrity?
Sep 01, 2025A 22-year-old made a splash recently when he published a Wall Street Journal op-ed claiming that work-life balance makes you mediocre. He went on to brag about how sleeping less than 4 hours a night a...
Ep. 367: What if AI Doesn’t Get Much Better Than This?
Aug 25, 2025In recent years, it’s been hard not to react to the possibilities of generative AI without a mixture of euphoria or dread. But after OpenAI’s lackluster GPT-5 launch, a new, almost heretical-seeming q...
Ep. 366: How to Reinvent Your Life in 4 Months (Classic Episode from August, 2023)
Aug 18, 2025In this replay of one of the more popular episodes from the Deep Questions archives, originally aired in August ,2023, Cal explores some of his early strategies for cultivating a deeper life. Below ar...
Ep. 365: What Technology Wants (and How to Push Back)
Aug 11, 2025Why do we end up entangled with tools that don’t have our best interests in mind? How can we fix this situation? In this episode, Cal dives deep into the difference between additive and extractive tec...
Ep. 364: Metrics 101
Aug 04, 2025When Cal recently returned home from his time spent up in New England he set up a whole new set of daily metrics to track in the fall to keep him pointed toward the deep life. And they failed. Hard. I...
Ep. 363: Escaping the Digital Doldrums
Jul 28, 2025What does Walt Disney’s malaise in the 1940s have to do with our current struggles with our screens? In this episode, Cal uses a little-known story from Disney’s midlife to identify an effective strat...
Ep. 362: The Texting Dilemma
Jul 21, 2025When we think about unhealthy phone usage, we think about the flashing apps, like TikTok and Instagram, in which billions of dollars have been spent to grab our attention. In this episode, Cal points ...
Ep. 361: Do You Need an App Blocker?
Jul 14, 2025Are you worried that you’re using your phone too much? An app blocker might make sense. But how do they work, and which one is right for you? In this episode, Cal goes deep into the motivation, techno...