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Deep Questions with Cal Newport

Deep Questions with Cal Newport

Cal Newport

  • 33 minutes 40 seconds
    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

    30 July 2026, 10:00 am
  • 1 hour 10 minutes
    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

    27 July 2026, 10:00 am
  • 1 hour 18 minutes
    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

    20 July 2026, 10:00 am
  • 31 minutes 41 seconds
    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

    16 July 2026, 10:00 am
  • 1 hour 4 minutes
    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

    13 July 2026, 10:00 am
  • 19 minutes 56 seconds
    Do Managers Actually Understand AI? (I’m Not So Sure.) | AI Reality Check

    Cal Newport takes a critical look at recent AI News. Video from today’s episode: youtube.com/calnewportmedia (0:00) Does business actually understand AI? (2:52) Quote #2 (6:20) Taking a step back (7:06) Quote #3 (11:39) Quote #4 (17:02) Idea for journalists Links: Buy Cal’s latest book, “Slow Productivity” at www.calnewport.com/slow https://www.nytimes.com/2026/07/02/world/europe/germany-sap-ai-jobs-skilled-workers.html https://futurism.com/artificial-intelligence/nvidia-ceo-begs-execs-stop-fired-ai https://finance.yahoo.com/sectors/technology/articles/marc-andreessen-says-every-large-033008122.html https://finance.yahoo.com/sectors/technology/articles/sam-altman-says-initially-wrong-132000485.html 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

    9 July 2026, 10:00 am
  • 1 hour 5 minutes
    Should I Turn Off the Internet? (Lessons From a Family That Did) | Monday Advice

    It’s a dream a lot of us have: to finally say “enough!”, and turn off the internet inside our homes, returning us to a lifestyle that requires more presence, introspection, and connection. But is this even possible? And what would it really be like? In this episode, Cal seeks answers to these questions by talking to Chris Moody, a journalism professor at Appalachian State, who lives with his wife and young son in a cabin with no internet, television, or cellular signal. 

     

    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 turn off the internet?

    (3:28) Interview with Chris Moody

    (1:02:58) Cal’s closing remarks

     

    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:

     

    This show is sponsored by Better Help:

    https://www.betterhelp.com/deepquestions

    https://www.calderalab.com/deep

    https://www.shopify.com/deep

    https://www.pipedrive.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

    6 July 2026, 10:00 am
  • 59 minutes 48 seconds
    Can I Be a Digital Minimalist in 2026? | Monday Advice

    Back in 2019, Cal published one of the first books arguing that we rethink our personal relationship with online tools. Can his advice still work in an age of TikTok and ChatGPT? In today’s episode, Cal dives deep into the r/DigitalMinimalism sub-reddit to see what advice contemporary digital minimalists are following and offers his own thoughts and recommendations. 

     

    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) Can I be a Digital Minimalist in 2026?

    (39:13) How can I capture notes if I’m land lining?

    (40:39) For cognitive fitness, is it better to be handwriting or typing?

    (42:07) A note on art museum visits

    (43:46) Reactions to an article about AI and software engineering

    (49:39) What the Deep Life really is

    (50:46) What Cal read

    (52:08) What Cal watched

     

    Books:

     The Jewish Way to a Good Life (Rabbi Shira Stuntman)

     

    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.youtube.com/watch?v=XeNNYMJwZtI

    https://www.reddit.com/r/digitalminimalism/

    https://www.reddit.com/r/digitalminimalism/comments/1tv0k77/for_the_past_2_years_ive_been_living_like_its_the/

    https://www.reddit.com/r/digitalminimalism/comments/1to631b/three_years_of_digital_minimalism_the_rewiring_is/

    https://www.reddit.com/r/digitalminimalism/comments/1ty27lz/limited_my_14f_screen_time_to_3_hours_a_day_and/

    https://www.reddit.com/r/digitalminimalism/comments/1tm9rce/where_do_you_still_find_human_curation/

    https://www.reddit.com/r/digitalminimalism/comments/1txskw9/deciding_once_instead_of_every_morning_is_the/

    https://www.reddit.com/r/digitalminimalism/comments/1u74dob/ran_a_30day_intentional_solitude_experiment/

    https://www.normaltech.ai/p/why-ai-hasnt-replaced-software-engineers

     

    Thanks to our Sponsors:

     

    https://www.vanta.com/deepquestions

    https://www.drinklmnt.com/deep

    https://www.expressvpn.com/deep

    https://www.wealthfront.com/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

    29 June 2026, 10:00 am
  • 22 minutes 4 seconds
    Dear AI Companies: Stop the “Doom Trolling” | AI Reality Check

    Cal Newport takes a critical look at recent AI News.


    Video from today’s episode: youtube.com/calnewportmedia


    (0:00) Stop the “doom trolling”

    (6:53) Cal’s recent New York Times article

    (9:00) Cal’s argument

    (10:16) The 2nd option

    (12:54) Conclusion

    (15:58) Stop playing along with Doom Trolling game

    (20:09) Use the term “doom trolling”


    Links:

    Buy Cal’s latest book, “Slow Productivity” at www.calnewport.com/slow 

    https://www.nytimes.com/2026/06/17/opinion/ai-dangerous-openai-anthropic.html

    https://www.nytimes.com/2023/03/24/opinion/yuval-harari-ai-chatgpt.html

    https://www.newyorker.com/science/annals-of-artificial-intelligence/what-kind-of-mind-does-chatgpt-have

    https://www.nytimes.com/2026/04/07/opinion/anthropic-ai-claude-mythos.html

    https://www.anthropic.com/institute/recursive-self-improvement

    https://x.com/sapinker/status/2067231673268273547

    https://x.com/edzitron/status/2067308832053936276


    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

    25 June 2026, 10:00 am
  • 57 minutes 58 seconds
    Am I Lazy or Overstimulated? | Monday Advice

    Cal Newport explains about if you're lazy or overstimulated in episode 410 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) Am I lazy or overstimulated?

    (28:29) A reaction to Cal’s recent New Yorker article

    (38:23) Positive lessons from box offices  successes of Gen Z films 

    (46:24) An old school tool for a woodshed

    (47:32) A new solution to landlining

    (49:30) What Cal is reading


    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.newyorker.com/culture/open-questions/instead-of-taking-your-job-ai-might-transform-it

    https://www.youtube.com/watch?v=tKGhxMi50y8

    https://aprilowens.substack.com/p/the-art-we-actually-need


    Thanks to our Sponsors: 


    https://www.scribe.how/deep

    https://www.shopify.com/deep

    https://www.cozyearth.com/deep (Use code “DEEP”)

    https://www.calderalab.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

    22 June 2026, 10:00 am
  • 29 minutes 25 seconds
    Was the Mythos Ban Justified? (Good Idea. Bad Execution.) | AI Reality Check

    Cal Newport takes a critical look at recent AI News.


    Video from today’s episode: youtube.com/calnewportmedia


    (0:00) Was the Mythos ban justified?

    (5:32) Is Fable 5 actually dangerous?

    (11:03) Is Fable 5 without guardrails actually a unique national security concern?

    (15:13) Should the government be more involved with AI?


    Links:

    Buy Cal’s latest book, “Slow Productivity” at www.calnewport.com/slow 

    https://www.anthropic.com/glasswing

    https://www.nytimes.com/2026/06/09/technology/anthropic-ai-claude-fable-mythos.html

    https://x.com/DavidSacks/status/2065853007619588171

    https://www.economist.com/business/2026/06/14/donald-trumps-blocking-of-anthropic-is-capricious-and-chaotic

    https://x.com/deanwball/status/2066151868556865860

    https://x.com/GaryMarcus/status/2066166713453060512

    https://x.com/DavidSacks/status/2065853007619588171

    https://www.nytimes.com/2026/04/07/opinion/anthropic-ai-claude-mythos.html

    https://www.whitehouse.gov/presidential-actions/2026/06/promoting-advanced-artificial-intelligence-innovation-and-security/


    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

    17 June 2026, 10:00 am
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