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Reading As an Act of Resistance (Notes on Harvard’s Hum 10)
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A Better Way to Think About Tech
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Do Hard Things (Featuring: Jerry Seinfeld)
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When Productivity Theory Meets Practice
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Why Did Big Tech Stop Building Useful Products?
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“Rogue” AI Not Inevitable. It’s a Choice.
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An Unlikely Team Tackles AI Brain Rot
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A Stark Warning From a Former AI Doomer
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Combating the Whirlwind with a Single Sheet of Paper
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An Insider's Guide to AI Doom
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Kids Should *Not* Use Chatbots! (You Should Be Wary, Too…)
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The Truth About Brain Rot
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The AI Resistance is Forming. (Should You Join?)
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How Worrisome is GPT-6’s “Stealth Thinking”? | Tech Decoded
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How I’m Organizing My Life this Fall | Advice
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Did OpenAI Create “Secret AI Civilizations”? | Tech Decoded
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Rethinking the Deep Life Stack (Again!) | Monday Advice
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Has AI “Gone Rogue”? Let’s Look Closer… | Tech Decoded
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How to Build a Cognitive Training Plan | Monday Advice
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Classic Episode: How Do I Kick My Scrolling Habit? | Monday Advice
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How Do I Finish Meaningful Projects? | Monday Advice
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Does OpenAI’s Astra Mean AGI Has Arrived? | AI Reality Check
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Classic Episode: How Do I Learn Hard Things? | Monday Advice
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Did OpenAI’s Model “Go Rogue”? | AI Reality Check
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Why Do Digital Detoxes Fail? What Works Better? | Monday Advice
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Am I Optimizing Too Much? | Monday Advice
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Does Claude Have Private Thoughts? (Everyone Settle Down) | AI Reality Check
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Should I Use Notebooks More Often? (Cal’s Strategy) | Monday Advice
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Do Managers Actually Understand AI? (I’m Not So Sure.) | AI Reality Check
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Should I Turn Off the Internet? (Lessons From a Family That Did) | Monday Advice
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Can I Be a Digital Minimalist in 2026? | Monday Advice
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Dear AI Companies: Stop the “Doom Trolling” | AI Reality Check
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Am I Lazy or Overstimulated? | Monday Advice
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Was the Mythos Ban Justified? (Good Idea. Bad Execution.) | AI Reality Check
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Do I Need a “Brain Gym”? | Monday Advice
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Are We About to Lose Control of AI? | AI Reality Check
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Should I Press Pause? | Monday Advice
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How Do I Escape the “Busyness Singularity”? | Monday Advice
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Did AI Just “Solve” Math? (Let’s Take a Closer Look) | AI Reality Check
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How Do I Reclaim My Schedule? (w/ Laura Vanderkam) | Monday Advice
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Has AI Conquered Coding? (It’s Not So Simple…) | AI Reality Check
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Am I Addicted to My Phone? (w/ Anna Lembke) | Monday Advice
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Is AI About to “Eat Everything”? | AI Reality Check
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Do I Need a Digital Intervention? | Monday Advice
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Is the AI Doom Fever Breaking? | AI Reality Check
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Why Do Better Tools Make Me Worse at My Job? (w/ David Epstein) | Monday Advice
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Is AI About to Automate Every Office Job? | AI Reality Check
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How Do I Build “Cognitive Fitness”? | Monday Advice
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Is AI Trending Up or Down in 2026? | AI Reality Check
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Do I Need More Discipline? | Monday Advice
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Is Claude Mythos “Terrifying”? | AI Reality Check
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Ep. 400: Should I Embrace “Slow Technology”?
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AI Reality Check: Is AI Stealing Entry-Level Jobs?
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Ep. 399: Is Deep Work Still Possible in 2026?
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AI Reality Check: Can LLMs “Scheme”?
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Ep. 398: How Do I Find Purpose in a Distracted World? (w/ Arthur Brooks)
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AI Reality Check: Are LLMs a Dead End?
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Ep. 397: Why Do “Productivity Technologies” Make My Job Worse?
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AI Reality Check: Did AI Just Become Sentient?
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Ep. 396: Can I Learn To Love My Phone Again?
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AI Reality Check: Is the Economy About to Collapse?
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Ep. 395: Should I Try a “Social Media Pause”?
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AI Reality Check: Did the LLM Job Apocalypse Begin Last Week?
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Ep. 394: Do I Need a Better Planning System?
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Ep. 393: Can Movies Save Us From Our Phones?
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Ep. 392: Are “Micro-Streamers” the Future of Media? + Why Cal Spent $60 on a Task App
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Ep. 391: Is AI Reporting Broken? + Rethinking Morning Routines
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Ep. 390: What Happens When You Ditch Your Smartphone? + Assessing the Internet’s Latest Self-Help Sensation
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Ep. 389: Is the Internet Hijacking Ambition? + Escaping Messaging Hell
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Ep. 388: What’s Worrying Jon Haidt Now? + Should You Buy a Landline? (Cal just did…)
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Ep 387: Can Substack Save Journalism? + Viral Advice for Ignoring Your Phone
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Ep 386: Was 2025 a Great or Terrible Year for AI? (w/ Ed Zitron)
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Ep 385: Single-Purpose Notebooks (REPLAY)
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Ep 384: What Should I Read for a Deeper New Year?
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Ep 383: Why Is Everyone Talking About “Against the Machine”? (w/ Tyler Austin Harper)
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Ep. 382: Is the Internet Becoming Television?
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Ep. Ep 381: Life Advice from Legendary Writers
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Ep. 380: ChatGPT is Not Alive!
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Ep. 379: The Flexibility Myth
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Ep. 378: The Lost Art of Long Thinking
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Ep. 377: The Case Against Superintelligence
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Ep. 376: The Lincoln Protocol
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Ep. 375: Did OpenAI Just Kill Social Media?
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Ep. 374: This is Your Brain on Phones
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Ep. 373: The Internet’s Best Advice for Reinventing Your Life
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Ep. 372: Decoding TikTok’s Algorithm
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IN-DEPTH: Focus like a Nobel Prize Winner (w/ Brian Keating)
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Ep. 371: Is it Finally Time to Leave Social Media?
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Ep. 370: Deep Work in the Age of AI
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Ep. 369: Why Are We Getting Dumber? A Debate.
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IN-DEPTH: The Game of Life (w/ Tim Ferriss)
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Ep. 368: I Want Work-Life Balance. Am I Doomed to Mediocrity?
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Ep. 367: What if AI Doesn’t Get Much Better Than This?
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Ep. 366: How to Reinvent Your Life in 4 Months (Classic Episode from August, 2023)
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Ep. 365: What Technology Wants (and How to Push Back)
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Ep. 364: Metrics 101
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Ep. 363: Escaping the Digital Doldrums
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Ep. 362: The Texting Dilemma
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Ep. 361: Do You Need an App Blocker?
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Ep. 360: One-Page Productivity
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