Deep Questions with Cal Newport
How Worrisome is GPT-6’s “Stealth Thinking”? | Tech Decoded
Cal Newport takes a critical look at recent AI News. Video from today’s episode: youtube.com/calnewportmedia (0:00) How Worrisome is GPT-6’s “Stealth Thinking”? (8:58) Reasoning models (15:30) Astra (21:02) The Good (24:48) The Bad (28:28) The Hype Links: Buy Cal’s latest book, “Slow Productivity” at www.calnewport.com/slow https://www.youtube.com/watch?v=1QNsdr-Qx_I https://www.theinformation.com/articles/secret-technique-behind-openais-astra-model-sparks-security-concerns?rc=1ycz3a https://x.com/_NathanCalvin/status/2094957301564092914 https://x.com/sjgadler/status/2094959837691908214?s=61 https://x.com/merettm/status/2095023204993490967?s=20 https://arxiv.org/abs/2507.11473 Thanks to Jesse Miller for production and mastering and Nate Mechler for research and newsletter. Learn more about your ad choices. Visit podcastchoices.com/adchoices
How I’m Organizing My Life this Fall | Advice
It’s that time of year again when Cal tunes up his organizational systems for the onslaught of the fall. In this episode, Cal walks through the exact system he’s personally adopting for the next few months. He also discusses why such systems are key to thriving in our current frenetic technological world, why it’s important to continue to tweak your systems, and best practices for constructing your own setup. 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 (0:00) How I’m organizing my life this fall (24:36) An Irish novelist talks about her use of AI (30:11) Developing a more balanced approach to tech products (35:04) Cal’s opinion on an AI article (41:55) Large corporations move away from all enterprise AI (48:46) What Cal is up to August 2026 Books The New Dark Age (Nigel Biggar) Links: Buy Cal’s latest book, “Slow Productivity” at www.calnewport.com/slow Get a signed copy of Cal’s “Slow Productivity” at https://peoplesbooktakoma.com/event/cal-newport/ https://culturedcode.com/things/ https://www.timeblockplanner.com/ Thanks to our Sponsors: https://www.superhuman.com https://www.shopify.com/deep https://www.monarch.com (Use code “DEEP”) https://www.mybodytutor.com Thanks to Jesse Miller for production and mastering, Jay Kerstens for the intro music, and Nate Mechler for research and newsletter. Learn more about your ad choices. Visit podcastchoices.com/adchoices
Did OpenAI Create “Secret AI Civilizations”? | Tech Decoded
Cal Newport takes a critical look at recent AI News. Video from today’s episode: youtube.com/calnewportmedia (0:00) Does OpenAI create “secret AI civilizations”? (1:59) What’s the deal with “agent swarms”? (8:54) Should we be worried that the agents are plotting? (17:39) How should we be thinking about all of this? Links: Buy Cal’s latest book, “Slow Productivity” at www.calnewport.com/slow https://www.dwarkesh.com/p/openai-huggingface https://calnewport.com/has-ai-gone-rogue/ https://calnewport.com/are-we-at-war-with-ai-agent-civilizations/ Thanks to Jesse Miller for production and mastering and Nate Mechler for research and newsletter. Learn more about your ad choices. Visit podcastchoices.com/adchoices
Rethinking the Deep Life Stack (Again!) | Monday Advice
Back in 2023, Cal released an episode on a lifestyle design strategy I called the Deep Life Stack. Today, almost three years later, Cal revisits this idea and replaces it with a more robust concept that he calls “The Deep Life Map.” 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 (0:00) Rethinking the Deep Life stack (38:07) Too many interests and not enough time (47:29) Voluntary attention regulates acute immune responses in humans (55:34) A freelance musician and social media (1:09:08) What Cal is up to August 2026 Books An Inside Job (Daniel Silva) Three Years in Wonderland (Todd James Pierce) Links: Buy Cal’s latest book, “Slow Productivity” at www.calnewport.com/slow Get 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://www.nature.com/articles/s41562-026-02541-1 https://www.amazon.co.uk/stores/Cal-Newport/author/B001IGNR0U https://x.com/RyanHoliday Thanks to our Sponsors: https://www.surfshark.com/deepquestions https://www.quo.com/deep https://www.masterclass.com/deep https://www.notion.com/cal Thanks to Jesse Miller for production and mastering, Jay Kerstens for the intro music, and Nate Mechler for research and newsletter. Learn more about your ad choices. Visit podcastchoices.com/adchoices
Has AI “Gone Rogue”? Let’s Look Closer… | Tech Decoded
Cal Newport takes a critical look at recent AI News. Video from today’s episode: youtube.com/calnewportmedia (0:00) Has AI “Gone Rogue” (2:25) Observation #1 - Most Superhuman AI is well behaved (4:28) Observation #2 - A specific type of AI system is causing these problems (9:59) Observation #3 - This specific type of system is a bad idea (21:25) Observation #4 - The AI companies are negligent (27:04) Observation #5 - We can push back Links: Buy Cal’s latest book, “Slow Productivity” at www.calnewport.com/slow https://www.anthropic.com/news/investigating-incidents-cybersecurity-evals https://apnews.com/article/meta-ai-hacking-anthropic-irregular-openai-0e8061437da6779be962b24ac134a514 https://x.com/_NathanCalvin/status/2080685870877757551 https://huggingface.co/learn/agents-course/unit1/agent-steps-and-structure https://www.youtube.com/watch?v=DwAOHVBKTwg Sponsor: https://www.donedaily.com Thanks to Jesse Miller for production and mastering and Nate Mechler for research and newsletter. Learn more about your ad choices. Visit podcastchoices.com/adchoices
How to Build a Cognitive Training Plan | Monday Advice
In the world of physical health, we use so-called “key performance indicators” (KPIs) to help measure and improve our fitness. In today’s episode, Cal proposes a collection of three KPIs for measuring and improving your *cognitive* capabilities – a small step toward his larger vision of a cognitive fitness revolution. 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 (0:00) How to build a cognitive training plan (29:48) What is Cal’s opinion on information fatigue syndrome? (37:04) Comments on the new book, “Pardon Our French: The Parisian Way to a Happier Life” (40:17) An interesting way to think about AI and thinking (47:37) An article about Disneyland, high quality leisure, and deep living (57:53) What Cal is up to August 2026 Books The Laws of Thought (Tom Griffiths) This is For Everyone (Tim Berners-Lee) Into the Deep (Bob Ballard and Christopher Drew)202 Links: Buy Cal’s latest book, “Slow Productivity” at www.calnewport.com/slow Get 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://workplacepsychology.wordpress.com/2011/05/18/information-overload-when-information-becomes-noise/ https://scholarlykitchen.sspnet.org/2026/08/12/reading-between-the-lines-part-1-a-cognitive-framework-for-ai-in-scholarly-publishing/ https://pluralistic.net/2021/07/18/boredom-and-its-discontents-part-ii/ https://pluralistic.net/2026/08/12/insurance-value-of-biodiversity/ https://archive.ph/WvW1F Thanks to our Sponsors: https://www.calderalab.com/deep (Use code “DEEP) https://www.vanta.com/deepquestions https://www.gusto.com/deep https://www.babbel.com/deep Thanks to Jesse Miller for production and mastering, Jay Kerstens for the intro music, and Nate Mechler for research and newsletter. Learn more about your ad choices. Visit podcastchoices.com/adchoices
Classic Episode: How Do I Kick My Scrolling Habit? | Monday Advice
The best way to kick your scrolling habit is to introduce more “high quality leisure” into your life. But how do you accomplish this goal? In this replay of a classic episode from February, 2024, Cal walks through six new habits – what he calls a “high quality leisure toolkit” – for rebuilding your life around more meaningful activities. 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 (0:00) Confronting Your Phone (13:06) What does Cal think about Neil Postman’s “Amusing Ourselves To Death”? (17:45) Can you pursue high quality leisure after a day filled with deep work? (21:56) Can commercial breaks be used for high quality leisure? (25:04) Will digital minimalism work in an age of augmented reality? (31:26) How can a full time YouTuber practice digital minimalism? (38:34) How to share content online? (46:27) Cost-benefit analysis of technology usage (49:09) JRR Tolkien’s Search for Depth Links: https://twitter.com/explore/tabs/trending https://www.instagram.com/explore/tags/popular/hl=en https://www.tiktok.com/foryou?lang=en https://newcriterion.com/blogs/dispatch/the-consolations-of-fantasy Thanks to our Sponsors: https://www.cozyearth.com (Use code “DEEP”) https://www.shopify.com/deep https://www.monarch.com (Use code “DEEP”) Thanks to Jesse Miller for production, Jay Kerstens for the intro music, Kieron Rees for slow productivity music, and Mark Miles for mastering. Learn more about your ad choices. Visit podcastchoices.com/adchoices
How Do I Finish Meaningful Projects? | Monday Advice
Only 8% of people finish their yearly goals. At the same time, the percentage of people feeling a sense of meaning of purpose in their life is falling. These two numbers are connected: the more we struggle to accomplish meaningful projects, the less meaningful our lives might feel. In this episode, Cal looks back to a classic article he wrote nearly twenty years ago to both better understand why this problem is getting worse and how we can solve it. 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 (0:00) How do I finish meaningful projects? (39:36) A new study about children with cellphones having poorer reading comprehension (43:14) A nurse practitioner in search of deep work (45:45) Using AI to improve both your work and life (52:24) A recent Wall Street Journal article about AI and jobs (1:00:07) What Cal is up to July 2026 Books Orality and Literacy (Walter Ong) Lost (Rachel Harrington) Sapiens (Yuval Harari) More Everything Forever (Adam Becker) Disneyland the Rise of Automation (Roland Bethencourt) A Brief History of Intelligence (Max Bennett) Links: Buy Cal’s latest book, “Slow Productivity” at www.calnewport.com/slow Get 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://www.inc.com/marcel-schwantes/science-says-92-percent-of-people-dont-achieve-goals-heres-how-the-other-8-perce.html https://news.gallup.com/poll/711836/gen-zers-missing-sense-meaning-purpose-life.aspx https://calnewport.com/the-einstein-principle-accomplish-more-by-doing-less/ https://futureoftuesday.substack.com/p/techno-analog https://newsroom.ucla.edu/releases/owning-a-cell-phone-associated-with-poorer-reading-comprehension-schoolchildren https://www.wsj.com/business/big-companies-are-starting-to-hire-again-defying-predictions-of-ai-wipeout-f4974e99?mod=hp_lead_pos10 Thanks to our Sponsors: https://www.scribe.how/deep https://www.superhuman.com https://www.mybodytutor.com https://www.factormeals.com/deep50off Thanks to Jesse Miller for production and mastering, Jay Kerstens for the intro music, and Nate Mechler for research and newsletter. Learn more about your ad choices. Visit podcastchoices.com/adchoices
Does OpenAI’s Astra Mean AGI Has Arrived? | AI Reality Check
Cal Newport takes a critical look at recent AI News. Video from today’s episode: youtube.com/calnewportmedia (0:00) Does Open AI’s Astra mean AGI has arrived? (3:07) What actually happened? (11:35) What does this mean for mathematics? (21:35) What does this mean for OpenAI? Links: Buy Cal’s latest book, “Slow Productivity” at www.calnewport.com/slow https://x.com/polynoamial/status/2083467194663571701 https://x.com/deanwball/status/2083545756003176724?s=61 https://x.com/kevinroose/status/2083632335438905441 https://x.com/mattshumer_/status/2083595078233202919 https://x.com/polynoamial/status/2083478171975082334 https://x.com/__alpoge__/status/2083898804563243033 https://x.com/polynoamial/status/2083476852216369294 https://x.com/thomasfbloom/status/2083444983592284465 Sponsor: https://www.donedaily.com Thanks to Jesse Miller for production and mastering and Nate Mechler for research and newsletter. Learn more about your ad choices. Visit podcastchoices.com/adchoices
Classic Episode: How Do I Learn Hard Things? | Monday Advice
In this replay of a classic episode from January 1st, 2024, Cal walks through the process of learning hard things. The good news is that most people can learn most things. The bad news is that learning is harder than we think. This advice has never been more relevant for those looking to move past the easy dopamine hits offered by their devices and find something deeper. 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 (0:00) Learning hard things (21:19) When it comes to taking notes, what really matters? (27:32) Can I fit all of my hobbies into my week? (31:12) Can YouTube teach me to be a better student? (37:37) How do I figure out what to learn next? (39:54) How do I learn something fast when I already have a busy schedule?- (46:24) CALL: How does “So Good They Can’t Ignore You” relate to “Slow Productivity”? (56:17) CASE STUDY: Slow Productivity affinity group (1:02:23) The 5 books Cal read in December 2023 Thanks to our Sponsors: https://www.monarch.com (Use code “DEEP”) https://www.calderalab.com/deep This show is brought to you by BetterHelp. Give online therapy a try at https://www.betterhelp.com/deepquestions December 2023 Books: Home Economics (Wendell Berry) Panora’s Box (Peter Biskind) Where the Deer and the Antelope Play (Nick Offerman) Who Wrote the Bible (Richard Elliott Friedman) The Exodus (Richard Elliott Friedman) Thanks to Jesse Miller for production, Jay Kerstens for the intro music, Kieron Rees for slow productivity music, and Mark Miles for mastering. Learn more about your ad choices. Visit podcastchoices.com/adchoices
Did OpenAI’s Model “Go Rogue”? | AI Reality Check
Cal Newport takes a critical look at recent AI News. Video from today’s episode: youtube.com/calnewportmedia (0:00) Did OpenAI’s model “go rogue” (11:29) The implications (11:42) Did this attack reveal surprising new capabilities we didn’t know AI systems possessed? (12:48) Did the system’s decision to escape the test environment and autonomously attack another company indicate an emerging malicious intent in AI? (16:28) What changed led to this attack occurring? (27:32) Who should care about this story? Links: Buy Cal’s latest book, “Slow Productivity” at www.calnewport.com/slow https://huggingface.co/blog/security-incident-july-2026 https://openai.com/index/hugging-face-model-evaluation-security-incident/ https://www.wsj.com/tech/ai/openai-models-escaped-and-hacked-a-company-in-cybersecurity-test-gone-wrong-ee388506 https://thehill.com/policy/technology/5987397-openai-hugging-face-hack/ https://apnews.com/article/skynet-ai-terminator-artificial-intelligence-eb85da03a0161beaa5f3babc4331e93b https://www.ft.com/content/7e558951-0c69-459b-8bc8-2c6021d4402d?syn-25a6b1a6=1 https://federalnewsnetwork.com/all-news/2011/08/dhs-anonymous-used-rudimentary-tools-to-hack-contractor/ Thanks to Jesse Miller for production and mastering and Nate Mechler for research and newsletter. Learn more about your ad choices. Visit podcastchoices.com/adchoices
Why Do Digital Detoxes Fail? What Works Better? | Monday Advice
Why do digital detoxes fail to create lasting change? What works better? To answer these questions, Cal draws from the book “A Brief History of Intelligence” to reveal the relevant neuroscience at play, and then use this understanding to figure out a better method for improving your relationship with your devices. 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 (0:00) Why do digital detoxes fail? (28:28) An article on the phone algorithm addiction (35:13) Follow up on the Brad Stulberg interview (40:21) A policy article on digital addiction (52:34) Deep work in the age of AI (57:46) What Cal is up to Links: Buy Cal’s latest book, “Slow Productivity” at www.calnewport.com/slow Get 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://www.nytimes.com/2018/02/04/us/politics/online-addictions-cut-back-screen-time.html https://www.nytimes.com/2026/07/14/opinion/culture/phone-algorithm-addiction.html https://www.splunk.com/en_us/blog/learn/goodharts-law.html https://www.healthaffairs.org/content/forefront/digital-addiction-public-health-problem-public-health-law-solution Thanks to our Sponsors: https://www.masterclass.com/deep https://www.gusto.com/deep https://www.expressvpn.com/deep https://www.vanta.com/deepquestions Thanks to Jesse Miller for production and mastering, Jay Kerstens for the intro music, and Nate Mechler for research and newsletter. Learn more about your ad choices. Visit podcastchoices.com/adchoices
Am I Optimizing Too Much? | Monday Advice
Cal Newport talks with Brad Stulberg to explain the optimization paradox in Episode 414 of the Deep Questions podcast. 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 (0:00) The Optimization Paradox (2:12) Interview with Brad Stulberg (35:12) Health optimization (1:09:16) Tail end development Links: Buy Cal’s latest book, “Slow Productivity” at www.calnewport.com/slow Get a signed copy of Cal’s “Slow Productivity” at https://peoplesbooktakoma.com/event/cal-newport/ Cal’s monthly book directory: bramses.notion.site/059db2641def4a88988b4d2cee4657ba? Thanks to our Sponsors: https://wealthfront.com/deep https://calderalab.com/deep https://cozyearth.com (Use code “DEEP”) Cal Newport is not a Wealthfront client. Wealthfront’s high-yield cash account: https://www.wealthfront.com/deep. This experience may not be representative of other Wealthfront clients, and there is no guarantee of future performance or success. Experiences will vary. Cal Newport receives cash compensation from Wealthfront Brokerage for paid endorsement in his podcast, creating a conflict of interest. The Cash Account, which is not a deposit account, is offered by Wealthfront Brokerage LLC, member FINRA/SIPC. Wealthfront Brokerage is not a bank. The base APY is 3.30% on cash deposits as of January 30, 2026, is representative, subject to change, and requires no minimum. If eligible for the overall boosted rate of 4.05% offered in connection with this promo, your boosted rate is also subject to change if the base rate decreases during the 3 month promo period. Additional terms and conditions apply, which can be found on wealthfront.com/deep. Funds in the Cash Account are swept to program banks, where it earns the variable APY. Investment advisory services are provided by Wealthfront Advisers LLC, an SEC-registered investment adviser. Securities investments: not bank deposits, bank-guaranteed or FDIC-insured, and may lose value. Thanks to Jesse Miller for production and mastering, Jay Kerstens for the intro music, and Nate Mechler for research and newsletter. Learn more about your ad choices. Visit podcastchoices.com/adchoices
Does Claude Have Private Thoughts? (Everyone Settle Down) | AI Reality Check
Cal Newport takes a critical look at recent AI News. Video from today’s episode: youtube.com/calnewportmedia (0:00) Anthropic’s new research report (2:05) Digging into the paper (3:32) High level tutorial on LLMs (6:18) Detail on annotations (13:50) What the Anthropic paper found (20:39) Why this is interesting research (26:28) Conclusion on consciousness Links: Buy Cal’s latest book, “Slow Productivity” at www.calnewport.com/slow https://www.anthropic.com/research/global-workspace https://x.com/RileyRalmuto/status/2074195587616964757 https://www.axios.com/2026/07/06/anthropic-claude-ai-conscious https://www.technologyreview.com/2026/07/09/1140293/anthropic-found-a-hidden-space-where-claude-puzzles-over-concepts/ Thanks to Jesse Miller for production and mastering and Nate Mechler for research and newsletter. Learn more about your ad choices. Visit podcastchoices.com/adchoices
Should I Use Notebooks More Often? (Cal’s Strategy) | Monday Advice
Tell me if this sounds familiar: you buy a beautiful notebook, excited by all its possibilities to help refine your thoughts and generate new insights. Then it sits unused until you forget about it. The problem is not *what* notebooks you own but instead *how* you use them. In this episode, Cal walks through the four different notebooks he owns, and the four different ways he uses them. 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 (0:00) Should I Use Notebooks More Often? (Cal’s Strategy) (30:11) Comments on a controversial article (33:18 ) Statistics about smartphone bans in schools (38:15) A practical question about remote work (40:57) A question about focus and the World Cup (46:08) What Cal is up to (48:12) What Cal is reading Books: Orality and Literacy: The Technologizing of the Word (Walter Ong) Lost (Rachel Hartigan) Links: Buy Cal’s latest book, “Slow Productivity” at www.calnewport.com/slow Get 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://www.msn.com/en-us/money/general/a-neurologist-claims-gen-z-has-a-lower-iq-than-millennials/ar-AA1XAIFu https://x.com/JimenaJuani/status/2072095851816620191?s=20 Thanks to our Sponsors: https://www.superhuman.com https://www.factormeals.com/deep50off https://www.monarch.com/deep https://www.mybodytutor.com Cal Newport is not a Wealthfront client. Thanks to Jesse Miller for production and mastering, Jay Kerstens for the intro music, and Nate Mechler for research and newsletter. Learn more about your ad choices. Visit podcastchoices.com/adchoices
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