
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 Elo 20251h 37min

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 are...
18 Elo 20251h 17min

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 Elo 20251h 2min

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 Elo 20251h 9min

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 Heinä 20251h 9min

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 Heinä 20251h 10min

Ep. 360: One-Page Productivity
Trying to stick to complicated time management systems without any breaks can eventually lead to burn out. But if you stop organizational efforts altogether, your life can become a stressful mess. In ...
7 Heinä 202557min





















