Ep. 27: Inside My Planning Discipline, the Joys and Sorrows of Slack, and Finding Depth Among Shallow Friends | DEEP QUESTIONS

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

A blockbuster new study out of MIT takes a closer look at the impact of writing with the help of AI. In today’s episode, Cal breaks down this paper with the help of author Brad Stulberg (who made wave...

30 Jun 20251h 48min

Back in 2023, Cal gave a detailed deep dive that described the three phases of scientific understanding of smartphones, social media, and kids. In today’s episode, Cal argues that we’ve entered a four...

23 Jun 20251h 2min

Few philosophers in recent memory have enjoyed as much attention as Byung-Chul Han. His mix of profundity and pithiness in tackling some of the big issues of the modern technical environment has made ...

16 Jun 20251h 12min