Deep Questions with Cal Newport

66:44

Combating the Whirlwind with a Single Sheet of Paper

Deep Questions with Cal Newport ·

2026/10/05

One of the more debilitating experiences in our current digital world is the sense of being trapped in relentless, reactive, busyness. This “whirlwind” can separate you from both ambition and presence, leaving you feeling flat and fried. In this episode, Cal discusses a simple trick he deploys when he finds himself in this state. It requires only a single sheet of paper.More from Cal Download Cal’s FREE guide to cultivating a deeper life: calnewport.com/ideas Learn more about Cal’s books:

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28:39

An Insider's Guide to AI Doom

Deep Questions with Cal Newport ·

2026/10/01

The conversation around AI harms has become incredibly heated in recent weeks. But it's also incredibly confusing. In this short explainer episode, Cal walks through the three major categories of beliefs around AI in the current moment and helps explain who belongs where and how they all relate to each other. If you're trying to keep up with AI news you have need to learn this framework.Chapters: (0:00) Intro (1:01) Why the debate is so heated (2:01) Group 1: The Doomers (rationalists and

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78:36

Kids Should *Not* Use Chatbots! (You Should Be Wary,...

Deep Questions with Cal Newport ·

2026/09/28

With all the recent discussion of the potential catastrophic impacts AI might cause in the future, we’re losing track of the significant harms it is already causing right now. In this episode, Cal goes deep into a serious and tragic topic that he recently learned about in a panel discussion about children and technology. He has an urgent warning for parents that has implications for all of us as well. Below are the questions covered in today's episode (with their timestamps). Get your questions

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52:34

The Truth About Brain Rot

Deep Questions with Cal Newport ·

2026/09/21

A recent New York Times op-ed reveals the true nature of “brain rot,” and in doing so reveals a much larger problem affecting us all. In this episode, Cal explores this broader problem then draws from an unlikely source from his childhood to help identify a dramatic solution.Below are the questions covered in today's episode (with their timestamps). Get your questions answered by Cal! Here’s the link: https://bit.ly/3U3sTvo Video from today’s episode: youtube.com/calnewportmedia (0:00) The

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71:56

The AI Resistance is Forming. (Should You Join?)

Deep Questions with Cal Newport ·

2026/09/14

After a week spent debating AI’s impact on humanity, Cal wants to turn his attention back to AI’s impact on humans. To support this shift, he brings on the writer Brad Stulberg who recently decided that he was “done” with AI. They explore whether this is a resistance movement in the making…Video from today’s episode: youtube.com/calnewportmedia More from Cal Download Cal’s FREE guide to cultivating a deeper life: calnewport.com/ideas Learn more about Cal’s books: calnewport.com/books Listen to

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39:04

How Worrisome is GPT-6’s “Stealth Thinking”? | Tech...

Deep Questions with Cal Newport ·

2026/09/10

Cal Newport takes a critical look at recent AI News.Video from today’s episode: youtube.com/calnewportmedia (0:00) How Worrisome is GPT-6’s “Stealth Thinking”? (8:58) Reasoning models (15:30) Astra (21:02) The Good (24:48) The Bad (28:28) The Hype Links: Buy Cal’s latest book, “Slow Productivity” at

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51:58

How I’m Organizing My Life this Fall | Advice

Deep Questions with Cal Newport ·

2026/09/07

It’s that time of year again when Cal tunes up his organizational systems for the onslaught of the fall. In this episode, Cal walks through the exact system he’s personally adopting for the next few months. He also discusses why such systems are key to thriving in our current frenetic technological world, why it’s important to continue to tweak your systems, and best practices for constructing your own setup.Below are the questions covered in today's episode (with their timestamps). Get your

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26:55

Did OpenAI Create “Secret AI Civilizations”? | Tech...

Deep Questions with Cal Newport ·

2026/09/03

Cal Newport takes a critical look at recent AI News.Video from today’s episode: youtube.com/calnewportmedia (0:00) Does OpenAI create “secret AI civilizations”? (1:59) What’s the deal with “agent swarms”? (8:54) Should we be worried that the agents are plotting? (17:39) How should we be thinking about all of this? Links: Buy Cal’s latest book, “Slow Productivity” at

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80:23

Rethinking the Deep Life Stack (Again!) | Monday Advice

Deep Questions with Cal Newport ·

2026/08/31

Back in 2023, Cal released an episode on a lifestyle design strategy I called the Deep Life Stack. Today, almost three years later, Cal revisits this idea and replaces it with a more robust concept that he calls “The Deep Life Map.”Below are the questions covered in today's episode (with their timestamps). Get your questions answered by Cal! Here’s the link: https://bit.ly/3U3sTvo Video from today’s episode: youtube.com/calnewportmedia (0:00) Rethinking the Deep Life stack (38:07) Too

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35:50

Has AI “Gone Rogue”? Let’s Look Closer… | Tech Decoded

Deep Questions with Cal Newport ·

2026/08/27

Cal Newport takes a critical look at recent AI News. Video from today’s episode: youtube.com/calnewportmedia (0:00) Has AI “Gone Rogue” (2:25) Observation #1 - Most Superhuman AI is well behaved (4:28) Observation #2 - A specific type of AI system is causing these problems (9:59) Observation #3 - This specific type of system is a bad idea (21:25) Observation #4 - The AI companies are negligent (27:04) Observation #5 - We can push back Links: Buy Cal’s latest book, “Slow Productivity”

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62:45

How to Build a Cognitive Training Plan | Monday Advice

Deep Questions with Cal Newport ·

2026/08/24

In the world of physical health, we use so-called “key performance indicators” (KPIs) to help measure and improve our fitness. In today’s episode, Cal proposes a collection of three KPIs for measuring and improving your *cognitive* capabilities – a small step toward his larger vision of a cognitive fitness revolution. Below are the questions covered in today's episode (with their timestamps). Get your questions answered by Cal! Here’s the link: https://bit.ly/3U3sTvo Video from today’s

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57:45

Classic Episode: How Do I Kick My Scrolling Habit? |...

Deep Questions with Cal Newport ·

2026/08/17

The best way to kick your scrolling habit is to introduce more “high quality leisure” into your life. But how do you accomplish this goal? In this replay of a classic episode from February, 2024, Cal walks through six new habits – what he calls a “high quality leisure toolkit” – for rebuilding your life around more meaningful activities.Below are the questions covered in today's episode (with their timestamps). Get your questions answered by Cal! Here’s the link: https://bit.ly/3U3sTvo Video

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64:53

How Do I Finish Meaningful Projects? | Monday Advice

Deep Questions with Cal Newport ·

2026/08/10

Only 8% of people finish their yearly goals. At the same time, the percentage of people feeling a sense of meaning of purpose in their life is falling. These two numbers are connected: the more we struggle to accomplish meaningful projects, the less meaningful our lives might feel. In this episode, Cal looks back to a classic article he wrote nearly twenty years ago to both better understand why this problem is getting worse and how we can solve it.Below are the questions covered in today's

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29:30

Does OpenAI’s Astra Mean AGI Has Arrived? | AI...

Deep Questions with Cal Newport ·

2026/08/06

Cal Newport takes a critical look at recent AI News. Video from today’s episode: youtube.com/calnewportmedia (0:00) Does Open AI’s Astra mean AGI has arrived? (3:07) What actually happened? (11:35) What does this mean for mathematics? (21:35) What does this mean for OpenAI? Links: Buy Cal’s latest book, “Slow Productivity” at

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75:43

Classic Episode: How Do I Learn Hard Things? | Monday...

Deep Questions with Cal Newport ·

2026/08/03

In this replay of a classic episode from January 1st, 2024, Cal walks through the process of learning hard things. The good news is that most people can learn most things. The bad news is that learning is harder than we think. This advice has never been more relevant for those looking to move past the easy dopamine hits offered by their devices and find something deeper.Below are the questions covered in today's episode (with their timestamps). Get your questions answered by Cal! Here’s the

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33:40

Did OpenAI’s Model “Go Rogue”? | AI Reality Check

Deep Questions with Cal Newport ·

2026/07/30

Cal Newport takes a critical look at recent AI News.Video from today’s episode: youtube.com/calnewportmedia (0:00) Did OpenAI’s model “go rogue” (11:29) The implications (11:42) Did this attack reveal surprising new capabilities we didn’t know AI systems possessed? (12:48) Did the system’s decision to escape the test environment and autonomously attack another company indicate an emerging malicious intent in AI? (16:28) What changed led to this attack occurring? (27:32) Who should care

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70:41

Why Do Digital Detoxes Fail? What Works Better? |...

Deep Questions with Cal Newport ·

2026/07/27

Why do digital detoxes fail to create lasting change? What works better? To answer these questions, Cal draws from the book “A Brief History of Intelligence” to reveal the relevant neuroscience at play, and then use this understanding to figure out a better method for improving your relationship with your devices. Below are the questions covered in today's episode (with their timestamps). Get your questions answered by Cal! Here’s the link: https://bit.ly/3U3sTvo Video from today’s episode:

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78:30

Am I Optimizing Too Much? | Monday Advice

Deep Questions with Cal Newport ·

2026/07/20

Cal Newport talks with Brad Stulberg to explain the optimization paradox in Episode 414 of the Deep Questions podcast. Below are the questions covered in today's episode (with their timestamps). Get your questions answered by Cal! Here’s the link: https://bit.ly/3U3sTvo Video from today’s episode: youtube.com/calnewportmedia (0:00) The Optimization Paradox (2:12) Interview with Brad Stulberg (35:12) Health optimization (1:09:16) Tail end development Links: Buy Cal’s latest book,

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31:41

Does Claude Have Private Thoughts? (Everyone Settle...

Deep Questions with Cal Newport ·

2026/07/16

Cal Newport takes a critical look at recent AI News. Video from today’s episode: youtube.com/calnewportmedia (0:00) Anthropic’s new research report (2:05) Digging into the paper (3:32) High level tutorial on LLMs (6:18) Detail on annotations (13:50) What the Anthropic paper found (20:39) Why this is interesting research (26:28) Conclusion on consciousness Links: Buy Cal’s latest book, “Slow Productivity” at

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64:12

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

Deep Questions with Cal Newport ·

2026/07/13

Tell me if this sounds familiar: you buy a beautiful notebook, excited by all its possibilities to help refine your thoughts and generate new insights. Then it sits unused until you forget about it. The problem is not *what* notebooks you own but instead *how* you use them. In this episode, Cal walks through the four different notebooks he owns, and the four different ways he uses them. Below are the questions covered in today's episode (with their timestamps). Get your questions answered by Cal

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