
Deep Questions with Cal Newport
460 episodes — Page 1 of 10
A Stark Warning From a Former AI Doomer
Combating the Whirlwind with a Single Sheet of Paper
An Insider's Guide to AI Doom
Kids Should *Not* Use Chatbots! (You Should Be Wary, Too…)
The Truth About Brain Rot
The AI Resistance is Forming. (Should You Join?)
How Worrisome is GPT-6’s “Stealth Thinking”? | Tech Decoded
How I’m Organizing My Life this Fall | Advice
Did OpenAI Create “Secret AI Civilizations”? | Tech Decoded
Rethinking the Deep Life Stack (Again!) | Monday Advice
Has AI “Gone Rogue”? Let’s Look Closer… | Tech Decoded
How to Build a Cognitive Training Plan | Monday Advice
Classic Episode: How Do I Kick My Scrolling Habit? | Monday Advice
How Do I Finish Meaningful Projects? | Monday Advice
Does OpenAI’s Astra Mean AGI Has Arrived? | AI Reality Check
Classic Episode: How Do I Learn Hard Things? | Monday Advice
Did OpenAI’s Model “Go Rogue”? | AI Reality Check
Why Do Digital Detoxes Fail? What Works Better? | Monday Advice
Am I Optimizing Too Much? | Monday Advice
Does Claude Have Private Thoughts? (Everyone Settle Down) | AI Reality Check
Should I Use Notebooks More Often? (Cal’s Strategy) | Monday Advice
Do Managers Actually Understand AI? (I’m Not So Sure.) | AI Reality Check
Should I Turn Off the Internet? (Lessons From a Family That Did) | Monday Advice
Can I Be a Digital Minimalist in 2026? | Monday Advice
Dear AI Companies: Stop the “Doom Trolling” | AI Reality Check
Am I Lazy or Overstimulated? | Monday Advice
Was the Mythos Ban Justified? (Good Idea. Bad Execution.) | AI Reality Check
Do I Need a “Brain Gym”? | Monday Advice
Are We About to Lose Control of AI? | AI Reality Check
Should I Press Pause? | Monday Advice
How Do I Escape the “Busyness Singularity”? | Monday Advice
Did AI Just “Solve” Math? (Let’s Take a Closer Look) | AI Reality Check
How Do I Reclaim My Schedule? (w/ Laura Vanderkam) | Monday Advice
Has AI Conquered Coding? (It’s Not So Simple…) | AI Reality Check
Am I Addicted to My Phone? (w/ Anna Lembke) | Monday Advice
Is AI About to “Eat Everything”? | AI Reality Check
Do I Need a Digital Intervention? | Monday Advice
Is the AI Doom Fever Breaking? | AI Reality Check
Why Do Better Tools Make Me Worse at My Job? (w/ David Epstein) | Monday Advice
Is AI About to Automate Every Office Job? | AI Reality Check
How Do I Build “Cognitive Fitness”? | Monday Advice
Is AI Trending Up or Down in 2026? | AI Reality Check
Do I Need More Discipline? | Monday Advice
Is Claude Mythos “Terrifying”? | AI Reality Check
Ep. 400: Should I Embrace “Slow Technology”?
AI Reality Check: Is AI Stealing Entry-Level Jobs?
Ep. 399: Is Deep Work Still Possible in 2026?

AI Reality Check: Can LLMs “Scheme”?
bonusCal 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.
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.

AI Reality Check: Are LLMs a Dead End?
bonusCal 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.