Deep Questions with Cal Newport

• Ep. 357: What Worries the Internet’s Favorite Philosopher?

  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 him “the internet’s new favorite philosopher” (to quote The New Yorker). But is he saying that is making such an impact? In this episode, Cal seeks to find out. He reports back on five of the biggest ideas he encountered reading Han’s 2017 book, IN THE SWARM. He then answers listener questions and concludes with a WHAT TO READ segment where he tackles a pair of competing articles on AI’s abilities.Below are the questions covered in today's episode (with their timestamps). Get your questions answered by Cal! Here’s the link: bit.ly/3U3sTvoVideo from today’s episode:  youtube.com/calnewportmediaDeep Dive: What Worries the Internet’s Favorite Philosopher? [3:50]- What’s Cal’s writing schedule when traveling? [29:26]- How do I adapt to new job duties after making partner? [31:44]- Should I do memory training? [33:22]- Can you explain how creativity and productivity are related? [36:16]- How do Cal’s responsibilities fit into his lifestyle-centric plan? [39:33]CASE STUDY: A retiree adopts Cal’s principles [43:07]CALL: Adventure work [46:13]WHAT TO READ: Two Dueling Takes on AI’s Abilities [54:35]Links:Buy Cal’s latest book, “Slow Productivity” at calnewport.com/slowGet a signed copy of Cal’s “Slow Productivity” at peoplesbooktakoma.com/event/cal-newportCal’s monthly book directory: bramses.notion.site/059db2641def4a88988b4d2cee4657ba?theguardian.com/commentisfree/2025/jun/10/billion-dollar-ai-puzzle-break-downscientificamerican.com/article/inside-the-secret-meeting-where-mathematicians-struggled-to-outsmart-ai/arxiv.org/pdf/2504.01995arxiv.org/pdf/2503.21934Thanks to our Sponsors:This show is sponsored by BetterHelp:betterhelp.com/deepquestionsexpressvpn.com/deepshopify.com/deepmybodytutor.comThanks to Jesse Miller for production, Jay Kerstens for the intro music, and Mark Miles for mastering.

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• IN-DEPTH: The Art of Non-Conformity (w/ Chris Guillebeau)

  In this episode of IN-DEPTH, Cal is joined by Chris Guillebeau, the author of the new book, TIME ANXIETY, and creator of the beloved Art of Non-Conformity blog and World Domination Summit annual conferences. Cal and Chris reminisce about their old days as early advice bloggers and dive into his new ideas about re-thinking our relationship with time. Video from today’s episode:  youtube.com/calnewportmediaINTERVIEW: The Art of Non-Conformity (w/ Chris Guillebeau) [03:50]Links:https://www.calnewport.com/slowSponsors:https://www.donedaily.comThanks to Jesse Miller for production, Jay Kerstens for the intro music, Kieron Rees for the theme music, and Mark Miles for mastering.

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• Ep. 356: How Much Should We Work?

  The data shows knowledge workers really are more exhausted and more prone to burnout than ever before. But why? In this episode, Cal draws inspiration from an unlikely source to help unpack this troubling trend and then suggest a perhaps radical solution. He then answers listeners’ questions and discusses his latest New Yorker article on the challenges of taming AI. As a bonus, he briefly discusses Cal Network’s new bestselling book.Find out more about Done Daily at DoneDaily.com!Below are the questions covered in today's episode (with their timestamps). Get your questions answered by Cal! Here’s the link: bit.ly/3U3sTvoVideo from today’s episode:  youtube.com/calnewportmediaDeep Dive: How Much Should We Work? [3:33]- What’s your advice on having a career backup plan? [28:27]- Do you know of any executive coaches who teach your principles? [30:33]- Is my retirement plan too ambitious? [35:13]- Are accountability support tools acceptable to use in order to build discipline? [38:43]- How can I identify if I have an inventory of "rare and valuable skills"? [41:21]CASE STUDY: Crafting a storytelling profession [43:14]CALL: Creating a life dashboard [46:14]TECH CORNER: Why Can’t We Tame AI? (Cal’s latest New Yorker article) [52:08]Links:Buy Cal’s latest book, “Slow Productivity” at calnewport.com/slowGet a signed copy of Cal’s “Slow Productivity” at peoplesbooktakoma.com/event/cal-newport/Cal’s monthly book directory: bramses.notion.site/059db2641def4a88988b4d2cee4657ba?newyorker.com/culture/open-questions/what-isaac-asimov-reveals-about-living-with-aiThanks to our Sponsors:drinklmnt.com/deeporacle.com/deepquestionsindeed.com/deepvanta.com/deepquestionsThanks to Jesse Miller for production, Jay Kerstens for the intro music, and Mark Miles for mastering.

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• Ep. 355: Quit Social Media (For Real This Time)

  A common complaint about social media skepticism is that we’re falling into a classic moral panic. We’ve been concerned about many past mass media technologies, and ultimately came to realize that they’re not so bad. So why would we expect anything different about social media? In this episode, Cal tackles this complaint, drawing on an unexpected analogy to find clarity. He then answers listener questions and discusses the books he read in May, but not before first confronting a truly bizarre (or, perhaps, brilliant) piece of art work created by a fan of the show.Find out more about Done Daily at DoneDaily.com!Below are the questions covered in today's episode (with their timestamps). Get your questions answered by Cal! Here’s the link: bit.ly/3U3sTvoVideo from today’s episode:  youtube.com/calnewportmediaDeep Dive: Quit Social Media [6:18]- How can I become a better, more analytical thinker?  [23:04] - How can I stay motivated, productive, and balanced while working mostly alone during my first remote internship? [28:56]- How much time should I dedicate to developing secondary skills? [30:10]- How does TikTok seem to know so much about me? [32:09]- What are the best workflow strategies when using AI agents? [43:45]CASE STUDY: A simple, analog approach to productivity [49:31]CALL: Too focused on metrics [53:15]MAY BOOKS: The 5 Books Cal Read in May 2025 [1:03:19]May Books:Building: A Carpenter’s Notes on Life & the Art of Good Work (Mark Ellison)Thoreau’s Axe (Caleb Smith)9 Innings (Daniel Okrent)Let Them (Mel Robbins)Against the Machine (Paul Kingsnorth)Links:Buy Cal’s latest book, “Slow Productivity” at calnewport.com/slowGet a signed copy of Cal’s “Slow Productivity” at peoplesbooktakoma.com/event/cal-newport/Cal’s monthly book directory: bramses.notion.site/059db2641def4a88988b4d2cee4657ba?amazon.com/Four-Days-Week-Life-Changing-Well-Being/dp/0063382431/rcalnewport.com/on-ultra-processed-content/podcasts.apple.com/us/podcast/cal-newport-5-28-19/id814550071?i=1000647135862rehearsal.so/blog/how_to_stay_in_flow_while_using_cursor_or_windsurfThanks to our Sponsors:cozyearth.com/deepshopify.com/deepharrys.com/deepcalderalab.com/deepThanks to Jesse Miller for production, Jay Kerstens for the intro music, Kieron Rees for the slow productivity music, and Mark Miles for mastering.

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• Ep. 354: The Workload Fairytale

  A few years ago, in a spirit of post-pandemic experimentation, multiple countries ran formal trials to test a radical idea: shortening the workweek. In this episode, Cal returns to the results of these trials to identify an astounding finding that has critical implications about how we work in the 21st century and how this could be made much better. He then answers listener questions and concludes with a tech corner that addresses a simple question: when will AI begin to automate most of my work?Find out more about Done Daily at DoneDaily.com!Below are the questions covered in today's episode (with their timestamps). Get your questions answered by Cal! Here’s the link: bit.ly/3U3sTvoVideo from today’s episode:  youtube.com/calnewportmediaDeep Dive: The Workload Fairytale [3:39]- How would you rewrite A World Without Email to account for Slack? [18:16]- How should I manage multiple deadlines? [22:14]- How does Values-Based Lifestyle Centric Career Planning relate to Rutger Bregman's concept of Moral Ambition? [27:28]- How can I avoid burnout and use my career capital to find a less demanding job? [34:24]- Should I do my weekly plan on Sunday night to avoid the scaries? [40:32]CASE STUDY: A lawyer argues in front of the New York Court of Appeals [42:57]CALL: What exactly is considered task switching? [47:15]TECH CORNER: When will AI automate my job? [56:04]Links:Buy Cal’s latest book, “Slow Productivity” at calnewport.com/slowGet a signed copy of Cal’s “Slow Productivity” at peoplesbooktakoma.com/event/cal-newport/Cal’s monthly book directory: bramses.notion.site/059db2641def4a88988b4d2cee4657ba?bbc.com/news/business-57724779theguardian.com/money/2023/feb/21/four-day-week-uk-trial-success-patterndw.com/en/german-firms-tested-4-day-workweek-heres-the-outcome/a-70685885calnewport.com/ai-and-work-some-predictions/Thanks to our Sponsors:udacity.com/deeplandroverusa.comcalderalab.com/deepThanks to Jesse Miller for production, Jay Kerstens for the intro music, Kieron Rees for the slow productivity music, and Mark Miles for mastering.

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