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

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 waves online recently with his reaction to its findings), picking apart the role of AI in deep work activities. Cal then answers listeners questions, and presents a twist on his typical final segment in which he now describes what he is not reading this week, which provides him a thinly-concealed excuse to rant about AI coverage.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: Should We Fear Cognitive Debt? [2:15]Can AI be creative? [44:35]What’s the smallest change I can make to address my disorganization? [48:31]How do I find time for personal projects? [53:12]How should I choose my next internship? [1:06:08]How did you develop your goal-setting philosophy? [1:11:46]CALL: Inbox Zero and Notion [1:14:50]CASE STUDY: A Thoreau Schedule [1:24:01]WHAT I’M (NOT) READ: AI CEO’s hot takes on work [1:32:49]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?fortune.com/2025/06/20/openai-ceo-sam-altman-ai-phds-entry-level-corporate-job-cuts-what-is-left-gen-z-college-gradautes/Thanks to our Sponsors: shipstation.com/deepsmalls.com (Use code “DEEP”)notion.com/calharrys.com/deepThanks to Jesse Miller for production, Jay Kerstens for the intro music, and Mark Miles for mastering.

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 fourth phase; one that will finally lead to (perhaps rapid) cultural changes about what we think is appropriate when it comes to these tools and kids. He then answers listener questions and describes a recent book he enjoyed in his new WHAT TO READ segment.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 Smartphones Haven’t Defeated Us. Yet. [2:27]Should I temporarily rent a separate space to write my first book? [23:09]What should I do when waiting for AI while coding? [25:29]How should 11 years old boys get organized? [29:31]How can I develop my “soft skills” for my career? [33:54]How can my husband find his ideal career path? [38:48]CASE STUDY: A new dad incorporating lifestyle-centric career planning [43:25]CALL: Hand written notes [47:08]WHAT TO READ: The Explorer’s Gene [55:27]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?nytimes.com/2025/06/18/opinion/parents-smartphones-tiktok-facebook.htmlpapers.ssrn.com/sol3/papers.cfm?abstract_id=5256747tonyneufeld.blogThanks to our Sponsors: cozyearth.com/deepmackweldon.com (Promo code “DEEPQUESTIONS”)calderalab.com/deepgrammarly.com/podcastThanks to Jesse Miller for production, Jay Kerstens for the intro music, and Mark Miles for mastering.

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.

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.

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.

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.

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.

Summer is here. It’s time to slow down. In this episode, Cal discusses his radically simplified summer schedule and then suggests you similarly inject some “seasonality” into your life, offering tips for finding a slower gear without tanking your job. He then answers listener questions and reacts to the most important AI article that you likely missed last week. 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: Summer Schedules [5:25]- How should I structure my summer vacation with a significant injury? [27:40]- How do I learn the secrets to publication if the faculty doesn’t know I exist? [32:10]- Should I even attempt long-term content or is it too hard? [33:31]- How can I develop a deliberate practice for crafting narratives for technical documents? [44:33]- Is there an alternative to formal education to improve quantitative skills? [45:13]CASE STUDY: A father balances his different roles [47:40]CALL #1: Finding a side hustle [51:16]CALL #2: College student wondering the tips to focus better [56:02]CAL REACTS: Is the AI boom slowing? [1:07:01]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?wsj.com/tech/ai/meta-is-delaying-the-rollout-of-its-flagship-ai-model-f4b105f7Thanks to our Sponsors:grammarly.com/podcastvanta.com/deepquestionsshopify.com/deepcozyearth.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.

When we think about important accomplishments, we think about grinding through long hours of work. But is this really necessary? In this episode, Cal turns to the lives of two famous authors to argue that sometimes a slow and steady approach can work just as well in the end, while making the journey more sustainable along the way. He then answers listener questions and concludes with a Tech Corner segment about a ridiculous new claim from the world of AI. 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: https://bit.ly/3U3sTvo Video from today’s episode:  youtube.com/calnewportmedia Deep Dive: It’s Okay to Slow Down [2:28]- How should I tell people my email responses will be delayed without using an autoresponder? [18:07]- Should I read for quantity or quality? [20:31]- How does “one email address” per project work and how do I implement it? [24:51]- Can you comment on Conan O’Brien’s burner phone? [30:42]- Am I working hard enough to get tenure? [38:00] CASE STUDY: Email processing protocol [44:25]CALL #1: Organizing creative work [49:19]CALL #2: Fan update about Inbox Zero [53:37]TECH CORNER: A.I. Welfare is a PR Stunt [58:36] Links:Buy Cal’s latest book, “Slow Productivity” at www.calnewport.com/slowGet a signed copy of Cal’s “Slow Productivity” at https://peoplesbooktakoma.com/event/cal-newport/Cal’s monthly book directory: bramses.notion.site/059db2641def4a88988b4d2cee4657ba?https://thestory.au/articles/daily-routines-famous-writers/https://youtu.be/cM8HlKoJCHA?si=N-UjnFu-4q-mTJEBhttps://www.nytimes.com/2025/04/24/technology/ai-welfare-anthropic-claude.html Thanks to our Sponsors: This episode is sponsored by BetterHelp. Give online therapy a try at https://www.betterhelp.com/deepquestions and get on your way to being your best self!https://www.mybodytutor.comhttps://www.oracle.com/deepquestionshttps://www.expressvpn.com/deep Thanks to Jesse Miller for production, Jay Kerstens for the intro music, Kieron Rees for the slow productivity music, and Mark Miles for mastering.

Tyler Cowen recently wrote an article arguing that spending lots of time online is in fact a good thing. In this episode, Cal looks deeper at Cowen’s argument and finds some surprising common ground. The internet can be a major source of good in your life, he argues, but only if you use it in the right way. He then answers listener questions and reviews the books he read in April.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: Making the Internet Good Again [5:06]What are good activities for “deep breaks”? [28:38]How can I approach parenting without resenting the sacrifices to deep work? [31:36]How does the deep life compare to David Epstein’s book, “Range”? [38:06]What is the difference between a “winner-take-all” field of work and “auction” field of work? [41:12]Does “following your passion” have any connection to “lifestyle centric planning”? [47:39]CASE STUDY: Implementing the concept of “Eat The Frog” [52:48]CALL: Introducing seasonality and the meetings being the work [55:07]APRIL BOOKS: The 5 books Cal read in April, 2025 [1:06:08]I, Robot (Isaac Asimov)After Disney (Neil O’brien)The Baseball Book of Why (John McCollister)The Technology Republic (Alexander Karp and Nicholas Zamiska)Everything is Tuberculosis (John Green)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?thefp.com/p/the-case-for-living-onlineThanks to our Sponsors:shopify.com/deepauraframes.com [Use promo code “DEEPQUESTIONS”]indeed.com/deepharrys.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.