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Deep Questions with Cal Newport

Deep Questions with Cal Newport

460 episodes — Page 1 of 10

A Stark Warning From a Former AI Doomer

Oct 8, 20261h 17m

Combating the Whirlwind with a Single Sheet of Paper

Oct 5, 20261h 6m

An Insider's Guide to AI Doom

Oct 1, 202628 min

Kids Should *Not* Use Chatbots! (You Should Be Wary, Too…)

Sep 28, 20261h 18m

The Truth About Brain Rot

Sep 21, 202652 min

The AI Resistance is Forming. (Should You Join?)

Sep 14, 20261h 11m

How Worrisome is GPT-6’s “Stealth Thinking”? | Tech Decoded

Sep 10, 202639 min

How I’m Organizing My Life this Fall | Advice

Sep 7, 202651 min

Did OpenAI Create “Secret AI Civilizations”? | Tech Decoded

Sep 3, 202626 min

Rethinking the Deep Life Stack (Again!) | Monday Advice

Aug 31, 20261h 20m

Has AI “Gone Rogue”? Let’s Look Closer… | Tech Decoded

Aug 27, 202635 min

How to Build a Cognitive Training Plan | Monday Advice

Aug 24, 20261h 2m

Classic Episode: How Do I Kick My Scrolling Habit? | Monday Advice

Aug 17, 202657 min

How Do I Finish Meaningful Projects? | Monday Advice

Aug 10, 20261h 4m

Does OpenAI’s Astra Mean AGI Has Arrived? | AI Reality Check

Aug 6, 202629 min

Classic Episode: How Do I Learn Hard Things? | Monday Advice

Aug 3, 20261h 15m

Did OpenAI’s Model “Go Rogue”? | AI Reality Check

Jul 30, 202633 min

Why Do Digital Detoxes Fail? What Works Better? | Monday Advice

Jul 27, 20261h 10m

Am I Optimizing Too Much? | Monday Advice

Jul 20, 20261h 18m

Does Claude Have Private Thoughts? (Everyone Settle Down) | AI Reality Check

Jul 16, 202631 min

Should I Use Notebooks More Often? (Cal’s Strategy) | Monday Advice

Jul 13, 20261h 4m

Do Managers Actually Understand AI? (I’m Not So Sure.) | AI Reality Check

Jul 9, 202619 min

Should I Turn Off the Internet? (Lessons From a Family That Did) | Monday Advice

Jul 6, 20261h 5m

Can I Be a Digital Minimalist in 2026? | Monday Advice

Jun 29, 202659 min

Dear AI Companies: Stop the “Doom Trolling” | AI Reality Check

Jun 25, 202622 min

Am I Lazy or Overstimulated? | Monday Advice

Jun 22, 202657 min

Was the Mythos Ban Justified? (Good Idea. Bad Execution.) | AI Reality Check

Jun 17, 202629 min

Do I Need a “Brain Gym”? | Monday Advice

Jun 15, 202658 min

Are We About to Lose Control of AI? | AI Reality Check

Jun 11, 202620 min

Should I Press Pause? | Monday Advice

Jun 8, 202633 min

How Do I Escape the “Busyness Singularity”? | Monday Advice

Jun 1, 202648 min

Did AI Just “Solve” Math? (Let’s Take a Closer Look) | AI Reality Check

May 28, 202631 min

How Do I Reclaim My Schedule? (w/ Laura Vanderkam) | Monday Advice

May 25, 20261h 26m

Has AI Conquered Coding? (It’s Not So Simple…) | AI Reality Check

May 21, 202612 min

Am I Addicted to My Phone? (w/ Anna Lembke) | Monday Advice

May 18, 20261h 26m

Is AI About to “Eat Everything”? | AI Reality Check

May 14, 202631 min

Do I Need a Digital Intervention? | Monday Advice

May 11, 202643 min

Is the AI Doom Fever Breaking? | AI Reality Check

May 7, 202626 min

Why Do Better Tools Make Me Worse at My Job? (w/ David Epstein) | Monday Advice

May 4, 20261h 21m

Is AI About to Automate Every Office Job? | AI Reality Check

Apr 30, 202633 min

How Do I Build “Cognitive Fitness”? | Monday Advice

Apr 27, 202651 min

Is AI Trending Up or Down in 2026? | AI Reality Check

Apr 23, 20261h 13m

Do I Need More Discipline? | Monday Advice

Apr 20, 20261h 26m

Is Claude Mythos “Terrifying”? | AI Reality Check

Apr 16, 202624 min

Ep. 400: Should I Embrace “Slow Technology”?

Apr 13, 20261h 31m

AI Reality Check: Is AI Stealing Entry-Level Jobs?

Apr 9, 202616 min

Ep. 399: Is Deep Work Still Possible in 2026?

Apr 6, 20261h 3m

AI Reality Check: Can LLMs “Scheme”?

bonus

Cal Newport takes a critical look at recent AI News. Video from today’s episode: youtube.com/calnewportmedia ACT #1: Look Closer at the Article [1:20] ACT #2: A Closer Look at the Paper [3:21] ACT #3: But What About… [7:24] Links: Buy Cal’s latest book, “Slow Productivity” at www.calnewport.com/slow https://www.theguardian.com/technology/2026/mar/27/number-of-ai-chatbots-ignoring-human-instructions-increasing-study-says https://x.com/summeryue0/status/2025774069124399363 https://www.axios.com/2025/05/23/anthropic-ai-deception-risk Thanks to Jesse Miller for production and mastering and Nate Mechler for research and newsletter. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Apr 2, 202619 min

Ep 398Ep. 398: How Do I Find Purpose in a Distracted World? (w/ Arthur Brooks)

Here’s a key question: Did technology like smartphones make us miserable, or were we already miserable and smartphones made it worse? To help figure out this answer, I talked to Arthur Brooks, the #1 New York Times bestselling author and Harvard professor, about this new book: The Meaning of Your Life: Finding Purpose in an Age of Emptiness. In our conversation, Brooks argues that our current Age of Emptiness began in the 1990s, but technology like smartphones and social media made it worse. We then discuss smart strategies for finding purpose in our current moment. Below are the questions covered in today's episode (with their timestamps). Get your questions answered by Cal! Send an email to [email protected]. Video from today’s episode: youtube.com/calnewportmedia INTERVIEW: How Do I Find Purpose in a Distracted World? (W/ Arthur Brooks) [1:44] INBOX: Tech employees being evaluated through LLM tokens [1:01:49] Can Cal comment on reading digital books? [1:07:35] WHAT CAL IS UP TO: What Cal is reading [1:13:00] Deep Work HQ update [1:14:37] Books: Mistborn (Brandon Sanderson) Links: Buy Cal’s latest book, “Slow Productivity” at calnewport.com/slow Get a signed copy of Cal’s “Slow Productivity” at peoplesbooktakoma.com/event/cal-newport/ Cal’s monthly book directory: bramses.notion.site/059db2641def4a88988b4d2cee4657ba?gizmodo.com/tech-employees-are-reportedly-being-evaluated-by-how-fast-they-burn-through-llm-tokens-2000736627 Thanks to our Sponsors: monarch.com (Use code “DEEP”)butcherbox.com/deepdrinklmnt.com/deepmeetfabric.com/deep Thanks to Jesse Miller for production, Jay Kerstens for the intro music, Nate Mechler for research and newsletter, and Mark Miles for mastering. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Mar 30, 20261h 17m

AI Reality Check: Are LLMs a Dead End?

bonus

Cal Newport takes a critical look at recent AI News. Video from today’s episode: youtube.com/calnewportmedia SUB QUESTION #1: What is Yan LeCun Up To? [2:55] SUB QUESTION #2: How is it possible that LeCun could be right about LLM’s begin a dead-end? We’ve been hearing non-stop recently about how fast they’re advancing. [14:55] SUB QUESTION #3: What would happen next if LeCun is right? [22:26] Links: Buy Cal’s latest book, “Slow Productivity” at www.calnewport.com/slow https://www.nytimes.com/2026/03/10/technology/ami-labs-yann-lecun-funding.html Thanks to Jesse Miller for production and mastering and Nate Mechler for research and newsletter. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Mar 26, 202630 min