Deep Questions with Cal Newport

In this episode of IN-DEPTH, Cal is joined by bestselling author and podcaster, Tim Ferriss. Tim rocketed to prominence with his 2007 book, “The Four Hour WorkWeek” which basically redefined a generation’s relationship with work, meaning, and the possibilities for building an interesting life. More recently, Tim created a card game! It’s called Coyote. And he created it with one of the top designers in the business, the same company that created Exploding Kittens.Video from today’s episode:  youtube.com/calnewportmediaINTERVIEW: The Game of Life (w/ Tim Ferriss) [3:16]Links:https://www.explodingkittens.com/products/coyoteSponsorshttps://www.reclaim.ai/calThanks to Jesse Miller for production, Kieron Rees for the theme music, and Mark Miles for mastering.

A 22-year-old made a splash recently when he published a Wall Street Journal op-ed claiming that work-life balance makes you mediocre. He went on to brag about how sleeping less than 4 hours a night and gaining 80 pounds helped him become a millionaire. In this episode, Cal wades into the furious debate this article sparked. He argues that once you look past the author’s dorm bro bravado, the kid does actually ask a good question. It’s just that his answers are lacking. Cal then tackles listener questions and reviews the books he read in August.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: I Want Work-Life Balance. Am I Doomed to Mediocrity? [1:06]Is it possible to stay focused when having to check my phone for text messages? [42:20]When did you switch back to your teaching schedule to your summer schedule? [44:05]How has your deep life evolved since Episode 1? [49:22]How can I stop obsessively checking my work email? [53:47]Can you summarize how values and strategic planning documents, birthday projects and lifestyle centric planning combine? [58:14]CASE STUDY: Organizing household admin [1:01:44]CALL: How to tame Trello cards [1:06:39]AUGUST BOOKS: The 5 books Cal read in August 2025 [1:13:26] Boundless Realm (Foxx Note)Collisions (Alec Nevala-Lee)Before the Birds Sang Words (Ken Bruce)Desperation Reef (T Jefferson Parker)Shift (Hugh Howey)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?https://www.youtube.com/watch?v=VX1XHMlX1J0Thanks to our Sponsors: ridge.com (use code “Cal”)drinklmnt.com/deepshopify.com/deepcalderalab.com/deepThanks to Jesse Miller for production, Jay Kerstens for the intro music, and Mark Miles for mastering.

In recent years, it’s been hard not to react to the possibilities of generative AI without a mixture of euphoria or dread. But after OpenAI’s lackluster GPT-5 launch, a new, almost heretical-seeming question has emerged: what if progress on AI is stalled well short of the wild predictions we were promised? In today’s episode, Cal draws from reporting on his recent New Yorker article to go deep into this question. What is going on with AI? How did we get here? What does it mean for our personal quest to live deeper lives? He then answers listener questions and ends by discussing his recent brush with literary acclaim.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 if AI Doesn’t Get Much Better Than This? [1:00]Will AI leave me unemployed in 10 years? [1:06:26]How should I structure the next 10 years as a recently retired college professor? [1:13:58]I just moved. How should I arrange my book collection? [1:15:36]CALL: Overhead tax [1:17:47]CAL REACTS: Ed Sheehan and the Booker Prize [1:27:55]Links:Buy Cal’s latest book, “Slow Productivity” at www.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-if-ai-doesnt-get-much-better-than-thisyoutube.com/watch?v=zju51INmW7Uyoutube.com/watch?v=Dtdue31z-X8youtube.com/watch?v=0SXCIfFK5r8youtube.com/shorts/dYZmGHOLNRUyoutube.com/watch?v=k82RwXqZHY8youtube.com/watch?v=qhnJDDX2hhUyoutube.com/watch?v=qbIk7-JPB2c&t=3syoutube.com/watch?v=k82RwXqZHY8youtube.com/shorts/JCImeOUVTJEThanks to our Sponsors: grammarly.com/podcastcozyearth.com/deepcalderalab.com/deepshipstation.com/deepThanks to Jesse Miller for production, Jay Kerstens for the intro music, and Mark Miles for mastering.

In this replay of one of the more popular episodes from the Deep Questions archives, originally aired in August ,2023, Cal explores some of his early strategies for cultivating a deeper life.Below are the questions covered in today's episode (with their timestamps). Get your questions answered by Cal! Here’s the link: bit.ly/3U3sTvoToday’s Deep Question: How can I reinvent my life in 4 months? [1:30]How can I ease into Cal's more advanced time management strategies? [36:58]Can unstructured work be a part of the deep life? [40:33]How can I stop changing my mind about what I want to do with my life? [44:41]Can I pursue the deep life if I need a job? [52:24]How do you pursue the deep life with depression? [56:49]Cover Reveal for Slow Productivity [1:05:27]Thanks to our Sponsors:This show is brought to you by Better Help.https://www.betterhelp.com/deepquestionshttps://www.mybodytutor.comhttps://www.miro.comhttps://www.shopify.com/deepThanks to Jesse Miller for production, Jay Kerstens for the intro music, and Mark Miles for mastering.

Why do we end up entangled with tools that don’t have our best interests in mind? How can we fix this situation? In this episode, Cal dives deep into the difference between additive and extractive technologies, telling a story that weaves old technology with old versions of modern tools, testimony from recent trials to ideas from leading technology critics – all in the service of improving your relationship with tools. He then answers listener questions and discusses the books he read in July, 2025.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/3U3sTvoVideo from today’s episode:  youtube.com/calnewportmediaDeep Dive: What Technology Wants (and How to Push Back) [:54]- Do project trackers work? [34:54]- Is there a downside scenario to engineering wonder? [39:14]- What types of people should I surround myself with? [43:00]- Can you explain your different audiences? [45:02]CALL: Shifting from medical work to a PhD [50:41]JULY BOOKS: The 5 Books that Cal Read in July, 2025 [57:33]L.A. Story (Bill Plunkett)Disney’s Land (Richard Snow)Ingenious (Richard Munson)Original Sin (Jake Tapper and Alex Thompson)Wool (Hugh Howey)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://substack.com/@priscillaharvey1/note/c-133662492https://www.yahoo.com/news/zuckerberg-tells-court-facebook-no-171222971.htmlhttps://www.vanityfair.com/news/story/mark-zuckerberg-is-so-over-facebook-friends?srsltid=AfmBOoo4dysXG_2rXWDJaKnSdG6CfbCqf0O_8op_R1phpz5GQPx2F4XAhttps://www.youtube.com/watch?v=R7jar4KgKxshttps://pluralistic.net/2022/11/28/enshittification/https://www.youtube.com/watch?v=_Ai-fC-2Bpohttps://www.emarketer.com/content/openai-hires-its-first-cmo-kate-rouch-foreshadowing-adshttps://www.youtube.com/watch?v=qfUpEWAKPf8&t=2350sThanks to our Sponsors:https://www.expressvpn.com/deephttps://www.oracle.com/deepquestionshttps://www.indeed.com/deephttps://www.calderalab.com/deepThanks to Jesse Miller for production, Jay Kerstens for the intro music, and Mark Miles for mastering.

When Cal recently returned home from his time spent up in New England he set up a whole new set of daily metrics to track in the fall to keep him pointed toward the deep life. And they failed. Hard. In this episode, Cal dissects why metrics matter, why they’re easy to mess up (including the mistakes he made), and how to use them correctly (including how he corrected his own setup). He then answers listener questions and discusses a recent AI article that got him all hot and bothered.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: Metrics 101 [2:10]How should I navigate the “grey area” when deciding to make a career change? [24:45]Do you have a framework for young people to develop deep critical thinking? [27:36]What should a father of 4 kids do for his next career move? [32:34]Can skills from a high-pressure call center carry over to a career in cybersecurity? [35:36]Should I have anticipated that my job was going to end? [38:36]CALL: Returning back to work after a summer break [43:14]CASE STUDY: Pursuing a hobby while combating digital doldrums [46:47]WHAT I’M (NOT) READING: Vibe Reporting on AI [55:52]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/2025/07/28/arts/video-games-artificial-intelligence.htmlThanks to our Sponsors: vanta.com/deepquestionssmalls.com/deepshopify.com/deep1password.com/deepThanks to Jesse Miller for production, Jay Kerstens for the intro music, Kieron Rees for segment music, and Mark Miles for mastering.

What does Walt Disney’s malaise in the 1940s have to do with our current struggles with our screens? In this episode, Cal uses a little-known story from Disney’s midlife to identify an effective strategy for escaping the nerve-deadening, dull state created by spending more and more of your professional and personal life on screens. He then answers listener questions (with an unusual level of spiciness), tries to calm himself with a reprise of the SLOW PRODUCTIVITY CORNER theme music, and concludes with a discussion of a recent essay he wrote about how no one really knows anything about AI.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: [1:47]How should I pursue two different goals after leaving my software engineering career? [21:10]Should I leave my business analyst job and buy a retail business? [24:32]I’ve tried writing for editors (and publications) before with no success. Any suggestions on how to break through? [30:08]How do I convince my company that AI assistance is not the answer? [35:27]Is inspiration perishable like Naval Ravikant says? [38:11]CALL: Inbox anxiety [43:15]CASE STUDY: A public school teacher with a blog [51:27]WHAT I’M WRITING: No One Knows Anything About AI [59:13]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?amusingplanet.com/2019/01/walt-disneys-backyard-railway-carolwood.htmlyoutu.be/KyfUysrNaco?si=uE6tJkPuFhdnbla2&t=2490calnewport.com/no-one-knows-anything-about-ai/Thanks to our Sponsors: drinklmnt.com/deepcozyearth.com/deepcalderalab.com/deepshipstation.com/deepThanks to Jesse Miller for production, Jay Kerstens for the intro music, and Mark Miles for mastering.

When we think about unhealthy phone usage, we think about the flashing apps, like TikTok and Instagram, in which billions of dollars have been spent to grab our attention. In this episode, Cal points to an unassuming culprit that may be just as responsible: simple messaging apps. He explores research that connects the social stress of pending messages to phone addiction, and explores ways to free yourself from constant messaging without having to isolate yourself socially. He then answers listener questions and discusses what he’s been reading.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 Texting Dilemma [5:35]How can I structure my mornings with my sales job if I don’t have two hours for deep work? [31:44]How should I handle mandatory overtime at my aerospace job? [33:18]How can I handle too many open loops with my shutdown ritual? [35:54]How can I better organize communication with my university students? [40:38]Should I take on extra-curricular roles during my first year of my PhD? [44:00]CALL: Household chore task list [48:01]CASE STUDY: 30-day declutter [51:45]WHAT TO READ: An author quits social media [59:45]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?sciencedirect.com/science/article/abs/pii/S0747563214007626journals.uchicago.edu/doi/10.1086/691462pmc.ncbi.nlm.nih.gov/articles/PMC9671478/carolinecrampton.com/im-done-with-social-media/Thanks to our Sponsors: calderalab.com/deepmiro.comshopify.com/deepgrammarly.com/podcastThanks to Jesse Miller for production, Jay Kerstens for the intro music, and Mark Miles for mastering.

Are you worried that you’re using your phone too much? An app blocker might make sense. But how do they work, and which one is right for you? In this episode, Cal goes deep into the motivation, technology, and ultimate end game of this distraction fighting technology. He then answers listener questions and discusses some intriguing comments he’s been seeing about limits to AI’s ability to code.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: Do You Need an App Blocker? [4:35]- How do I succeed with task management? [29:07]- How can I put boundaries on my administrative work for my university job? [33:58]- How should I manage X if I only use it on my desktop? [39:31]- How should I read through my weekly collection of newsletters? [41:11]- What do you think about Polyphasic sleep to prepare for deep work? [44:22]CASE STUDY: A ticketing system in action [45:21]WHAT TO READ: On the Limits of “Vibe Coding” [50:58]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?sciencefocus.com/science/youre-not-actually-addicted-to-your-smartphonenytimes.com/2020/01/20/style/quit-smartphone.htmlsupport.apple.com/guide/iphone/get-started-with-screen-time-iphbfa595995/iosyoutu.be/OuizzRCALCU?si=FqHzEEFdq7k4ao13x.com/AglaiaCodes/status/1942636133248061590x.com/GaryMarcus/status/1942478390323552588/photo/1Thanks to our Sponsors: This show is sponsored by BetterHelp:betterhelp.com/deepquestionsmybodytutor.comexpressvpn.com/deepindeed.com/deepThanks to Jesse Miller for production, Jay Kerstens for the intro music, and Mark Miles for mastering.

Trying to stick to complicated time management systems without any breaks can eventually lead to burn out. But if you stop organizational efforts altogether, your life can become a stressful mess. In this episode, Cal taps the wisdom of an elite running coach to devise what he calls one-page productivity: a minimum time management system, meant to be run for limited periods to help you recharge, but that also maintains just enough organization that you can avoid disaster. He argues such maintenance modes should be an important part of any time management practice. Cal then answers listener questions and concludes by reviewing the books he read in June 2025.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: One-Page Productivity [1:52]How do you approach decisions when you’re torn between two reasonable options? [18:17]How can I navigate teaching with phone addicted teenagers? [22:06]Have you considered using LLM’s to assist in your writing? [28:03]How many “thinking” walks do you take each week? [32:31]Do you have any recommendations for learning new material outside of the structured framework of a course? [35:00]CASE STUDY: A son explains his parents lifestyle engineering [37:21]CALL: Setting up workflows as a manager [41:09]JUNE BOOKS: The 5 Books Cal Read in June, 2025 [52:05]The Magic of Code (Samuel Arbesman)In the Swarm (Byung-Chul Han)The Fear Index (Robert Harriss)The Explore’s Gene (Alex Hutchinson)Skywalking (Dale Pollock)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/athletic/6453809/2025/06/27/bruce-bochy-walking-exercise-creativity/Thanks to our Sponsors:cozyearth.com (Use code “DEEP”)oracle.com/deepquestionsvanta.com/deepquestionsshopify.com/deepThanks to Jesse Miller for production, Jay Kerstens for the intro music, and Mark Miles for mastering.

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.