Deep Questions with Cal Newport Transcripts

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”?

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

AI Reality Check: Are LLMs a Dead End?

Ep. 397: Why Do “Productivity Technologies” Make My Job Worse?

AI Reality Check: Did AI Just Become Sentient?

Ep. 396: Can I Learn To Love My Phone Again?

AI Reality Check: Is the Economy About to Collapse?

Ep. 395: Should I Try a “Social Media Pause”?

AI Reality Check: Did the LLM Job Apocalypse Begin Last Week?

Ep. 394: Do I Need a Better Planning System?

Ep. 393: Can Movies Save Us From Our Phones?

Ep. 392: Are “Micro-Streamers” the Future of Media? + Why Cal Spent $60 on a Task App

Ep. 391: Is AI Reporting Broken? + Rethinking Morning Routines

Ep. 390: What Happens When You Ditch Your Smartphone? + Assessing the Internet’s Latest Self-Help Sensation

Ep. 389: Is the Internet Hijacking Ambition? + Escaping Messaging Hell

Ep. 388: What’s Worrying Jon Haidt Now? + Should You Buy a Landline? (Cal just did…)

Ep 387: Can Substack Save Journalism? + Viral Advice for Ignoring Your Phone

Ep 386: Was 2025 a Great or Terrible Year for AI? (w/ Ed Zitron)

Ep 385:

Ep 383: Why Is Everyone Talking About “Against the Machine”? (w/ Tyler Austin Harper)

Ep. 382: Is the Internet Becoming Television?

Ep. Ep 381: Life Advice from Legendary Writers

Ep. 380: ChatGPT is Not Alive!

Ep. 379: The Flexibility Myth

Ep. 378: The Lost Art of Long Thinking

Ep. 377: The Case Against Superintelligence

Ep. 376: The Lincoln Protocol

Ep. 375: Did OpenAI Just Kill Social Media?

Ep. 374: This is Your Brain on Phones

Ep. 373: The Internet’s Best Advice for Reinventing Your Life

Ep. 372: Decoding TikTok’s Algorithm

IN-DEPTH: Focus like a Nobel Prize Winner (w/ Brian Keating)

Ep. 371: Is it Finally Time to Leave Social Media?

Ep. 370: Deep Work in the Age of AI

Ep. 369: Why Are We Getting Dumber? A Debate.

IN-DEPTH: The Game of Life (w/ Tim Ferriss)

Ep. 368: I Want Work-Life Balance. Am I Doomed to Mediocrity?

Ep. 367: What if AI Doesn’t Get Much Better Than This?

Ep. 366: How to Reinvent Your Life in 4 Months (Classic Episode from August, 2023)