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

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 Apr 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 Apr 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 Apr 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 Apr 20241h 23min

One of the biggest problems afflicting knowledge workers in the digital age is frantic busyness; days filled with emails, chats, and meetings, without much to show for all the effort. In today’s episo...

1 Apr 20241h 16min

Imagine a world in which AI could handle your email inbox on your behalf. No more checking for new messages every five minutes. No more worries that people need you. No more exhausting cognitive conte...

25 Mar 20241h 36min

On his recent book tour, Cal found great success using a small notebook dedicated to developing a single idea. In this episode, he explores this “single-purpose notebook” strategy, identifying when it...

18 Mar 20241h 16min

What does the story of the rise of the singing superstar Jewel teach us about escaping busyness in our knowledge work jobs? In this episode, Cal makes the connection, extracting a key lesson about qua...

11 Mar 20241h 8min