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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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Ep. 359: Should We Fear Cognitive Debt?
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Ep. 358: Are Parents (Finally) Ready to Fight Smartphones?
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Ep. 357: What Worries the Internet’s Favorite Philosopher?
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IN-DEPTH: The Art of Non-Conformity (w/ Chris Guillebeau)
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Ep. 356: How Much Should We Work?
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Ep. 355: Quit Social Media (For Real This Time)
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Ep. 354: The Workload Fairytale
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Ep. 353: Summer Schedules
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Ep. 352: It’s Okay to Slow Down
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Ep. 351: Making the Internet Good Again
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Ep. 350: Is Inbox Zero Possible?
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Ep. 349: Sam Altman On Productivity
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IN-DEPTH: Architecting a Deep Life (w/ David Dewane)
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Ep. 348: Manage Your Time in 5 Minutes a Day
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Ep. 347: The Forgotten Phone Harms
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Ep. 346: Getting Smarter in a Dumb World
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Ep. 345: Are We Getting Dumber?
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Ep. 344: You Are Not a Cog
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Ep. 343: A Minimal Protocol for Taking Control of Your LIfe
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IN-DEPTH: Greatness on Trial (w/ Brad Stulberg and Clay Skipper)
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Ep. 342: The Good Life Algorithm
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Ep. 341: Drowning, Treading, or Swimming
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Ep. 340: Productivity Rain Dances
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Ep. 339: Let Brandon Cook
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Ep. 338: Why You’re Always Distracted
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Ep. 337: Hacking Remote Work
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Ep. 336: On Screens and Solitude
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Ep. 335: On Morning Routines
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Ep. 334: Hallmark Movies and the Deep Life
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Ep. 333: New Year Course Correction
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Ep. 332: Jesse Takeover!
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IN-DEPTH: The Comfort Crisis (w/ Michael Easter)
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Ep. 331: Money and the Deep Life
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Ep. 330: Tackling Social Media’s Hidden Dangers
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IN-DEPTH: Greatness vs. Contentment (w/ Kendra Adachi)
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Ep. 329: The Tao of Cal
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Ep. 328: Analog Mode
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Ep. 327: Would Kant Use TikTok?
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Ep. 326: Time to Unplug
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Ep. 325: Simple Focus Protocols
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Ep. 324: Taming Non-Work Tasks
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Ep. 323: Strategic Procrastination
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IN-DEPTH:The Productivity Trap (w/ Oliver Burkeman)
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Ep. 322: The Discipline Ladder
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Ep. 321: Escaping Your Phone
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Ep. 320: Jobs and the Deep Life
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IN-DEPTH: Systematic Depth (w/ Ryan Holiday)
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Ep. 319: Reclaim Your Time
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Ep. 318: Take a Break
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Ep. 317: The 10-Year Rule
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Ep. 316: Weekly Templates
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