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

The Optimization Paradox Explained | Monday Advice

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

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

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

Should I Turn Off the Internet? (Lesson 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

How Do I Get from Busy to Better? | Monday Advice

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

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

What has *Actually* Happened in AI 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: Single-Purpose Notebooks (REPLAY)

Ep 384: What Should I Read for a Deeper New Year?

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

Ep. 382: Is the Internet Becoming Television?

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)

Ep. 365: What Technology Wants (and How to Push Back)

Ep. 364: Metrics 101

Ep. 363: Escaping the Digital Doldrums

Ep. 362: The Texting Dilemma

Ep. 361: Do You Need an App Blocker?

Ep. 360: One-Page Productivity

Ep. 359: Should We Fear Cognitive Debt?

Ep. 358: Are Parents (Finally) Ready to Fight Smartphones?

Ep. 357: What Worries the Internet’s Favorite Philosopher?

IN-DEPTH: The Art of Non-Conformity (w/ Chris Guillebeau)

Ep. 356: How Much Should We Work?

Ep. 355: Quit Social Media (For Real This Time)

Ep. 354: The Workload Fairytale

Ep. 353: Summer Schedules

Ep. 352: It’s Okay to Slow Down

Ep. 351: Making the Internet Good Again

Ep. 350: Is Inbox Zero Possible?

Ep. 349: Sam Altman On Productivity

IN-DEPTH: Architecting a Deep Life (w/ David Dewane)

Ep. 348: Manage Your Time in 5 Minutes a Day

Ep. 347: The Forgotten Phone Harms

Ep. 346: Getting Smarter in a Dumb World

Ep. 345: Are We Getting Dumber?

Ep. 344: You Are Not a Cog

Ep. 343: A Minimal Protocol for Taking Control of Your Life

IN-DEPTH: Greatness on Trial (w/ Brad Stulberg and Clay Skipper)

Ep. 342: The Good Life Algorithm

Ep. 341: Drowning, Treading, or Swimming

Ep. 340: Productivity Rain Dances

Ep. 339: Let Brandon Cook

Ep. 338: Why You’re Always Distracted

Ep. 337: Hacking Remote Work

Ep. 336: On Screens and Solitude

Ep. 335: On Morning Routines

Ep. 334: Hallmark Movies and the Deep Life

Ep. 333: New Year Course Correction

Ep. 332: Jesse Takeover!

IN-DEPTH: The Comfort Crisis (w/ Michael Easter)

Ep. 331: Money and the Deep Life

Ep. 330: Tackling Social Media’s Hidden Dangers

IN-DEPTH: Greatness vs. Contentment (w/ Kendra Adachi)

Ep. 329: The Tao of Cal

Ep. 328: Analog Mode

Ep. 327: Would Kant Use TikTok?

Ep. 326: Time to Unplug

Ep. 325: Simple Focus Protocols

Ep. 324: Taming Non-Work Tasks

Ep. 323: Strategic Procrastination

IN-DEPTH: The Productivity Trap (w/ Oliver Burkeman)

Ep. 322: The Discipline Ladder

Ep. 321: Escaping Your Phone

Ep. 320: Jobs and the Deep Life

IN-DEPTH: Systematic Depth (w/ Ryan Holiday)

Ep. 319: Reclaim Your Time

Ep. 318: Take a Break

Ep. 317: The 10-Year Rule

Ep. 316: Weekly Templates

Ep. 315: The Surprising Math of Doing Less

Ep. 314: Elements of the Deep Life

Ep. 313: Structured Journaling

Ep. 312: Productivity Basics

Ep. 311: Finding Focus in Distracting Times

Ep. 310: Rethinking Discipline

Ep. 309: Deep Habits

Ep. 308: The Power of the Quiet Mind

Ep. 307: Ultra-Processed Content

Ep. 306: Defusing AI Panic

Ep. 305: Is Time Blocking Oppressive?

Ep. 304: Seinfeld on The Deep Life

Ep. 303: The Problem with Grand Goals

Ep. 302: Re-Enchanting Work

Ep. 301: Reclaiming Time and Focus (w/ Jordan Harbinger)

Ep. 300: Hidden Technology Traps

Ep. 299: Our Love/Hate Relationship with Personal Productivity

Ep. 298: Rethinking Attention

Ep. 297: The Deep Life Hardware

Ep. 296: Jane Austen’s To-Do List (LIVE)

Ep. 295: Artists Revolt Against Social Media

Ep. 294: A Tactical Assault on Busyness

Ep. 293: Can A.I. Empty My Inbox?

Ep. 292: Single-Purpose Notebooks

Ep. 291: Doing Better, Do Less

Ep. 290: Financing the Deep Life (w/ Noah Kagan)

Ep. 289: The Email Catastrophe

Ep. 288: Confronting Your Phone

Ep. 287: Minimalist Notes

Ep. 286: Rethinking Self Help

Ep. 285: The Productivity Paradox

Ep. 284: Feel-Good Productivity (w/ Ali Abdaal)

Ep. 283: How To Organize Your Life

Ep. 282: Slow Distractions

Ep. 281: Learning Hard Things

Ep. 280: Proven Rules for Deep Living (w/ Arthur Brooks)

Ep. 279: Confronting Overload

Ep. 278: How to Think

Ep. 277: From Chaos to Calm (in 1 day)

Ep. 276: Lazy or Disorganized?

Ep. 275: Accomplishing Hard Goals

Ep. 274: The Deep Life Stack v2.0

Ep. 273: A Deep Response to Distraction

Ep. 272: The Essential Tools (w/ David Epstein)

Ep. 271: The Long Game

Ep. 270: Depth vs. Distraction

Ep. 269: Don’t Get Started

Ep. 268: Stoicism and the Deep Life

Ep. 267: Why Are You Tired?

Ep. 266: Take Control of Your Technology Habits

Ep. 265: Big Ideas for Deeper Living

Ep. 264: IN-DEPTH: How to Master Change (with Brad Stulberg)

Ep. 263: Overhaul Your Life

Ep. 262: Creativity Hacking

Ep. 261: Control Your Time

Ep. 260: Make Haste Slowly

Ep. 259: The Four-Hour Work Day

Ep. 258: Godel’s Deep Life Stack

Ep. 257: Refusing Overwork

Ep. 256: Start with Discipline

Ep. 255: The Failure of Cybernetic Productivity

Ep. 254: The Laws of Less

Ep. 253: Making Time for What Matters (w/ Laura Vanderkam)

Ep. 252: The Deep Life Stack

Ep. 251: The Efficiency Trap

Ep. 250: In Defense of Thinking

Ep. 249: The Good Enough Job (w/ Simone Stolzoff)

Ep. 248: Decoding Overload

Ep. 247: The Productive Life

Ep. 246: Kids and Phones

Ep. 245: “Crazy” Productivity

Ep. 244: Thoughts on ChatGPT

Ep. 243: In The Weeds!

Ep. 242: The Simple Life

Ep. 241: The Virality Trap

Ep. 240: Disciplined Laziness

Ep. 239: On Time and Stress

Ep. 238: The Joys Of The Reading Life

Ep. 237: Reimagining The Internet

Ep. 236: Hacking Remote Work

Ep. 235: Is Productivity Overrated?

Ep. 234: Ambition without Burnout

Ep. 233: Escaping Your Tyrannical Inbox

Ep. 232: The Lumberjack Paradox

Ep. 231: Fight Burnout With Work Cycles

Ep. 230: How Well Are You Living?

Ep. 229: Developing Discipline

Ep. 227: Visions of the Deep Life?

Ep. 226: The Productivity Dragon

Ep. 225: Should I Become A Thriller Writer? (w/ J.T. Ellison)

Ep. 224: A World Without Twitter?

Ep. 223: Could This Meeting Have Been An Email?

Ep. 222: Did Cavemen Use To-Do Lists?

Ep. 221: Can Parents Do Deep Work?

Ep. 220: The Two Types of Ambition

Ep. 219: The Deep Reset

Ep. 218: Work vs. Meaning

Ep. 217: Slow Productivity Advice

Ep. 216: Deep Walking To Work Less

Ep. 215: RYAN HOLIDAY: Discipline Is Destiny

Ep. 214: Quiet Quitting

Ep. 213: The Art Of Saying No

Ep. 212: The Productivity Dragon Returns

Ep. 211: How Cal Organizes His Life

Ep. 210: Visions of a Deep Life

Ep. 209: Email and Living with Purpose

Ep. 208: To-Do Lists Are Inhumane

Ep. 207: A Digital Minimalism Intervention (w/ JAMIE KILSTEIN)

Ep 206: Striving to do less

Ep. 205: Why I’m a Bad Correspondent

Ep. 204: Deep Life Principles

Ep. 203: Taming Meetings

Ep. 202: TikTok Dismisses Facebook

Ep. 201: Making a Living Online

Ep. 200: Decoding the Deep Life

Ep. 199: Quieting an Ambitious Brain

Ep. 198: The Second Principle of Slow Productivity

Ep. 197: I’m Writing a New Book

Ep. 196: Shutting Down Anxiety

Ep. 195: Deep Walks

Ep. 194: The Surprising Math of Doing Less

Ep. 193: How do I read more?

Ep. 192: Habit Tune-Up Returns!

Ep. 191: Can We Fix the Internet?

Ep. 190: CALLS: Managing Idea Notebooks

Ep. 189: Why Did The Times Drop Twitter?

Ep. 188: The Books I Read in March 2022

Ep. 187: Helping 100K Employees Work Deeper

Ep. 186: The Power of “Day Batching”

Ep. 185: How Do I Escape Filter Bubbles?

Ep. 184: REPLAY: The Productivity Baby Steps

Ep. 183: Crazy or Deep?

Ep. 182: Cal’s Business Model

Ep. 181: Should I Quit My Lawyer Job?

Ep. 180: CALLS: Four Day Weeks Aren’t Enough

Ep. 179: Do Techniques Beat Talent?

Ep. 178: CALLS: On Doing Hard Things

Ep. 177: Is Ambition Worth It?

Ep. 176: CALLS: Taming Information Overload

Ep. 175: What is the Deep Life?

Ep. 174: CALLS: Thinking for Yourself

Ep. 173: What is Deep Work?

Ep. 172: CALLS: The Books I Read in January 2022

Ep. 171: Is Slow Productivity the Solution to Burnout?

Ep. 170: CALLS: Don’t Follow Your Passion

Ep. 169: How Do I Manage My Time?

Ep. 168: Should I Quit My Law Partner Job?

Ep. 167: What Do We Look Like? (Videos Are Now Live!)

Ep. 166: LISTENER CALLS: How I schedule podcasting

Ep. 165: Why Are We Burnt Out?

Ep. 163: The Books I Read in December 2021

Ep. 164: LISTENER CALLS: Training for Hard Intellectual Work

Ep. 162: LISTENER CALLS: Ambition and the Deep Life

Ep. 161: Should I Follow My Skill or My Passion?

Ep. 160: REPLAY: What is Discipline (and How Do I Get It?)

Ep. 159: REPLAY: How Much Should I Read?

Ep. 158: LISTENER CALLS: The Story of My First Book Deal

Ep. 157: JENNY BLAKE: Help Me Do Less!

Ep. 156: LISTENER CALLS: My Process for Writing New Yorker Articles

Ep. 155: Is Your Productivity System Leaking?

Ep. 154: LISTENER CALLS: Coping With a Hyperactive Job

Ep. 153: Why Was Ian Malcom Sent to Jurassic Park?

Ep. 152: LISTENER CALLS: The Magic of Autopilot Scheduling

Ep. 151: Should you move to the country?

Ep. 150: LISTENER CALLS: Finding More Family Time

Ep. 149: How Do I Tame Email?

Ep. 148: LISTENER CALLS: Decoding the Productive Pause

Ep. 147: Why Did I Never Join Social Media?

Ep. 146: LISTENER CALLS: A Revolution is Coming in Knowledge Work

Ep. 145: Is the Deep Life Compatible with Serving Humanity?

Ep. 144: LISTENER CALLS: Is Overload Necessary?

Ep. 143: Is the Era of Social Media Ending?

Ep. 142: LISTENER CALLS: Making Hard Work Routine

Ep. 141: Is the Era of Social Media Ending?

Ep. 140: LISTENER CALLS: Frustration and the Deep Life

Ep. 139: Am I Good at Time Management or Just Lazy?

Ep. 138: LISTENER CALLS: How I Read So Much

Ep. 137: Why Am I Uncomfortable With Facebook Backlash?

Ep. 136: LISTENER CALLS: Reversing Burnout

Ep. 135: Is Screen Time Bad?

Ep. 134: LISTENER CALLS: Returning to Deep Work After the Pandemic

Ep. 133: How Do I Defeat Distraction?

Ep. 132: LISTENER CALLS: Managing Non-Work Tasks

Ep. 131: The Elements of the Deep Life

Ep. 130: LISTENER CALLS: Leadership vs. Availability

Ep. 129: How Do I Get My Kid Off His Smartphone?

Ep. 128: LISTENER CALLS: The Art of “No”

Ep. 127: Does Productivity Diminish Leisure? (with Brad Stulberg)

Ep. 126: LISTENER CALLS: A Tour of My Home Offices

Ep. 125: What is Discipline (and How Do I Get It?)

Ep. 124: LISTENER CALLS: Preserving Depth in the Vast Shallows

Ep. 123: What Is My Daily Routine?

Ep. 122: LISTENER CALLS: Figuring Out Your Values

Ep. 121: Is Writing Everyday Overrated? (with Srini Rao)

Ep. 120: LISTENER CALLS: Students’ Diminishing Focus

Ep. 119: Does Accomplishment Require Overload?

Ep. 118: LISTENER CALLS: A Primer On My Planning Philosophy

Ep. 117: Should I Quit My Job to Become a Writer?

Ep. 116: RE-READING: Shop Class as Soulcraft (with Brad Stulberg and Steve Magness)

Ep. 115: JORDAN HARBINGER: What is the Future of Podcasting?

Ep. 114: LISTENER CALLS: Growing a Podcast Without Social Media

Ep. 113: How Do I Become a Deep Life Radical?

Ep. 111: How Do I Tame Distracting Thoughts?

Ep. 112: LISTENER CALLS: The Productivity Baby Steps

Ep. 110: LISTENER CALLS: Making the Deep Life Happen

Ep. 109: How Much Should I Read?

Ep. 108: LISTENER CALLS: Becoming Productive

Ep. 107: How Do I Stay Motivated on Long-Term Projects?

Ep. 106: LISTENER CALLS: Art Without Social Media

Ep. 105: Should I Read the News?

Ep. 104: LISTENER CALLS: Saying “No” Without Saying “No”

Ep. 103: What is the Relationship Between Order and Well-Being?