Ep. 24: Habit Tune-Up: Slaying the Productivity Hydra, Upgrading Careers, and Mastering a Difficult Job

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 37min

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 Aug 20251h 17min

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 2min

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 9min

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 9min

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 10min

Are 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...

14 Jul 202559min

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 Jul 202557min