Episode (200)
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Ep. 302: Re-Enchanting Work
May 27, 2024We 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 ...
Ep. 301: Reclaiming Time and Focus (w/ Jordan Harbinger)
May 20, 2024In 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...
Ep. 300: Hidden Technology Traps
May 13, 2024There 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...
Ep. 299: Our Love/Hate Relationship with Personal Productivity
May 06, 2024Cal 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...
Ep. 298: Rethinking Attention
Apr 29, 2024We 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...
Ep. 297: The Deep Life Hardware
Apr 22, 2024Why 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...
Ep. 296: Jane Austen’s To-Do List (LIVE)
Apr 15, 2024In 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...
Ep. 295: Artists Revolt Against Social Media
Apr 08, 2024In 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...
Ep. 294: A Tactical Assault on Busyness
Apr 01, 2024One 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...
Ep. 293: Can A.I. Empty My Inbox?
Mar 25, 2024Imagine 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...