Deep Questions with Cal Newport

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.
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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.
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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

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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.
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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

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.
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