IN-DEPTH: Systematic Depth (w/ Ryan Holiday)

We talk a lot on this show about how to organize and execute your work, but not enough about where to do it. In this episode, Cal explores the theory and practice of “adventure working,” in which you ...

27 Touko 20241h 22min

In this episode, the proverbial tables are turned, with Cal being interviewed by Jordan Harbinger about time, focus, and the quest for a slower notion of productivity. (This interview originally aired...

20 Touko 20241h 35min

There has been a lot of attention paid recently to the impact of technology like social media on the mental health of young people. But this is not the only technology trap lurking for this generation...

13 Touko 20241h 22min

Cal has been writing professionally about issues related to personal productivity for two decades. In today’s episode, he provides a short history of what he’s observed during this period about out co...

6 Touko 20242h 18min

We think of information as something neutral; a spotlight that helps illuminate the reality of the outside world. Accordingly, more information is better than less. In this episode, Cal pushes back on...

29 Huhti 20241h 19min

Why do you struggle with your grand attempts to escape distraction and aimlessness to make your life deeper? In this episode, Cal draws on an unexpected metaphor – Charles Babbage, Ada Lovelace, and t...

22 Huhti 20241h 26min

In the first ever live episode of Deep Questions, recorded at People’s Book in Takoma Park, MD, Cal extracts a modern productivity lesson from the tale of Jane Austen’s frustrated ambitions, before ta...

15 Huhti 20241h 21min

In this episode Cal takes a closer look at a growing trend of artists quitting social media and instead reverting to old-fashioned websites. Are these acts of principled sacrifice or a sustainable way...

8 Huhti 20241h 23min