IN-DEPTH: The Game of Life (w/ Tim Ferriss)
In 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...
4 Sep 20251h 57min
Ep. 368: I Want Work-Life Balance. Am I Doomed to Mediocrity?
A 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...
1 Sep 20251h 29min
Ep. 367: What if AI Doesn’t Get Much Better Than This?
In 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...
25 Aug 20251h 39min
Ep. 366: How to Reinvent Your Life in 4 Months (Classic Episode from August, 2023)
In 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...
18 Aug 20251h 19min
Ep. 365: What Technology Wants (and How to Push Back)
Why 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...
11 Aug 20251h 4min
Ep. 364: Metrics 101
When 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...
4 Aug 20251h 11min
Ep. 363: Escaping the Digital Doldrums
What 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...
28 Jul 20251h 11min
Ep. 362: The Texting Dilemma
When 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 ...
21 Jul 20251h 12min
