Deep Questions with Cal Newport

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