Deep Questions with Cal Newport
Cal Newport, a computer science professor and New York Times bestselling author, explores the impact of technology on society and the challenge of working and living deeply in an age of digital distractions. On this podcast, he answers questions from his readers and offers advice on cultivating focus, productivity, and meaning amidst the noise of modern life.
Episodes
The AI Resistance is Forming. (Should You Join?)
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
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How Worrisome is GPT-6’s “Stealth Thinking”? | Tech Decoded
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 www.calnewport.com/slow
https://www.youtube.com/watch?v=1QNsdr-Qx_I
h
How I’m Organizing My Life this Fall | Advice
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 you
Did OpenAI Create “Secret AI Civilizations”? | Tech Decoded
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 www.calnewport.co
Rethinking the Deep Life Stack (Again!) | Monday Advice
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 fro
Has AI “Gone Rogue”? Let’s Look Closer… | Tech Decoded
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 neg
How to Build a Cognitive Training Plan | Monday Advice
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 timestam
Classic Episode: How Do I Kick My Scrolling Habit? | Monday Advice
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 ep
How Do I Finish Meaningful Projects? | Monday Advice
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 t
Does OpenAI’s Astra Mean AGI Has Arrived? | AI Reality Check
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 www.calnewport.com/slow
https://x.com/polynoam
Classic Episode: How Do I Learn Hard Things? | Monday Advice
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 t
Did OpenAI’s Model “Go Rogue”? | AI Reality Check
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 emergin
Why Do Digital Detoxes Fail? What Works Better? | Monday Advice
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 y
Am I Optimizing Too Much? | Monday Advice
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 Bra
Does Claude Have Private Thoughts? (Everyone Settle Down) | AI Reality Check
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
Should I Use Notebooks More Often? (Cal’s Strategy) | Monday Advice
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 a
Do Managers Actually Understand AI? (I’m Not So Sure.) | AI Reality Check
Cal Newport takes a critical look at recent AI News.
Video from today’s episode: youtube.com/calnewportmedia
(0:00) Does business actually understand AI?
(2:52) Quote #2
(6:20) Taking a step back
(7:06) Quote #3
(11:39) Quote #4
(17:02) Idea for journalists
Links:
Buy Cal’s latest book, “Slow Productivity” at www.calnewport.com/slow
https://www.nytimes.com/2026/07/02/world/europe/germany-sap-a
Should I Turn Off the Internet? (Lessons From a Family That Did) | Monday Advice
It’s a dream a lot of us have: to finally say “enough!”, and turn off the internet inside our homes, returning us to a lifestyle that requires more presence, introspection, and connection. But is this even possible? And what would it really be like? In this episode, Cal seeks answers to these questions by talking to Chris Moody, a journalism professor at Appalachian State, who lives with his wife
Can I Be a Digital Minimalist in 2026? | Monday Advice
Back in 2019, Cal published one of the first books arguing that we rethink our personal relationship with online tools. Can his advice still work in an age of TikTok and ChatGPT? In today’s episode, Cal dives deep into the
r/DigitalMinimalism sub-reddit to see what advice contemporary digital
minimalists are following and offers his own thoughts and
recommendations.
Below are the qu
Dear AI Companies: Stop the “Doom Trolling” | AI Reality Check
Cal Newport takes a critical look at recent AI News.
Video from today’s episode: youtube.com/calnewportmedia
(0:00) Stop the “doom trolling”
(6:53) Cal’s recent New York Times article
(9:00) Cal’s argument
(10:16) The 2nd option
(12:54) Conclusion
(15:58) Stop playing along with Doom Trolling game
(20:09) Use the term “doom trolling”
Links:
Buy Cal’s latest book, “Slow Productivity
Am I Lazy or Overstimulated? | Monday Advice
Cal Newport explains about if you're lazy or overstimulated in episode 410 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) Am I lazy or overstimulated?
(28:29) A reaction to Cal’s recent New
Was the Mythos Ban Justified? (Good Idea. Bad Execution.) | AI Reality Check
Cal Newport takes a critical look at recent AI News.
Video from today’s episode: youtube.com/calnewportmedia
(0:00) Was the Mythos ban justified?
(5:32) Is Fable 5 actually dangerous?
(11:03) Is Fable 5 without guardrails actually a unique national security concern?
(15:13) Should the government be more involved with AI?
Links:
Buy Cal’s latest book, “Slow Productivity” at www.calnewp
Do I Need a “Brain Gym”? | Monday Advice
In the 1960s, doctors avoided people to avoid exercise. Then everything changed. Now physical fitness is a $100 billion industry. What would it look like if we got equally as serious about cognitive fitness? In this episode, Cal explores three tiers of cognitive fitness advice, ordered from least to most intense.
Below are the questions covered in today's episode (with their timestamps). Get yo
Are We About to Lose Control of AI? | AI Reality Check
Cal Newport takes a critical look at recent AI News.
Video from today’s episode: youtube.com/calnewportmedia
(0:00) Are we about to lose control of AI?
(3:04) How much should we be afraid of recursive self improvement?
(7:52) Are these fears justified?
(9:36) Faster software development doesn’t equal smarter AI
(12:25) These tools are completely controllable
(16:52) Taking a step back
Should I Press Pause? | Monday Advice
Sometimes the best way to get unstuck is to press pause on your busy life and take a moment to look toward new possibilities. But how is this possible if you can’t afford to literally stop everything and get away? In this episode, Cal explores different strategies for taking what he calls “mini-pauses” that can be integrated into even the most unforgiving of schedules.
Below are the questions c
How Do I Escape the “Busyness Singularity”? | Monday Advice
There has been lots of discussion recently about AI eliminating jobs. But what if the real fear is that AI will instead make existing jobs miserable? In this episode, Cal argues that LLM–based tools are poised to accelerate the worst aspects of pseudo-productivity to an absurd degree. He then shares five ideas for avoiding this fate in your own professional life.
Below are the questions covered
Did AI Just “Solve” Math? (Let’s Take a Closer Look) | AI Reality Check
Cal Newport takes a critical look at recent AI News.
Video from today’s episode: youtube.com/calnewportmedia
(0:00) Did AI just “solve” math?
(2:38) What OpenAI did
(6:30) Question #1 - Is this result that important?
(7:34) Question #2 - Does this mean LLMs are now smarter than human mathematicians?
(17:50) Question #3 - Does this mean all equally hard challenges will now be conquered by A
How Do I Reclaim My Schedule? (w/ Laura Vanderkam) | Monday Advice
It’s common to feel like you don’t have enough time in your schedule to build a life that’s both professionally successful and personally deep. But is this true? In today’s episode, Cal interviews time management expert Laura Vanderkam about her new book, BIG TIME, which argues that with the right tweaks and mindset you might be able to start getting more out of your life right away.
Below are t
Has AI Conquered Coding? (It’s Not So Simple…) | AI Reality Check
Cal Newport takes a critical look at recent AI News.
Video from today’s episode: youtube.com/calnewportmedia
(0:00) Has AI conquered coding?
(3:21) Lars Faye quote
(5:25) Skipping the struggle step
(6:42) Point #1
(7:08) Point #2
(7:28) Point #3
(7:39) Point #4
(8:35) Solution
Links:
Sign up for Cal’s newsletter at www.calnewport.com/ideas
Buy Cal’s latest book, “Slow Producti
Am I Addicted to My Phone? (w/ Anna Lembke) | Monday Advice
Many of us ask the question if phone addiction is similar to other addictions. In this episode, Cal is joined by the #1 New York Times bestselling author Anna Lembke to explore this question. They dive deep into her book, Dopamine Nation, that captivated readers.
Below are the questions covered in today's episode (with their timestamps). Get your questions answered by Cal! Send an email to pod
Is AI About to “Eat Everything”? | AI Reality Check
Cal Newport takes a critical look at recent AI News.
Video from today’s episode: youtube.com/calnewportmedia
(0:00) Is AI about to “eat everything”?
(2:53) What does the METR chart measure?
(8:08) What do these measurements actually capture?
(12:31-) How are the models getting better?
(21:26) Does this mean AI is about to “eat everything”?
(26:16) So, what’s with all of these hysteri
Do I Need a Digital Intervention? | Monday Advice
A new research study reveals that a surprisingly simple intervention into your digital life can yield massive benefits in only two weeks. In this episode, Cal takes a deep dive into this paper, detailing: the intervention, why it works, and tips for increasing your chances of success.
Below are the questions covered in today's episode (with their timestamps). Get your questions answered by Cal! H
Is the AI Doom Fever Breaking? | AI Reality Check
Cal Newport takes a critical look at recent AI News.
Video from today’s episode: youtube.com/calnewportmedia
(0:00) Is the AI doom fever breaking?
(4:30) Have the AI CEOs changed their tuen?
(7:23) Why did they change?
(11:21) Why did they ever think this was a good idea?
(24:26) Conclusion
Links:
Buy Cal’s latest book, “Slow Productivity” at www.calnewport.com/slow
https://www.you
Why Do Better Tools Make Me Worse at My Job? (w/ David Epstein) | Monday Advice
What can an obscure theory of industrial productivity teach us about producing better results in a distracted world? In this episode, Cal is joined by the #1 New York Times bestselling author David Epstein to explore this question. They dive deep into a chapter of Epstein’s new book, INSIDE THE BOX, that makes a surprising connection between the so-called “Theory of Constraints” and personal produ
Is AI About to Automate Every Office Job? | AI Reality Check
Cal Newport takes a critical look at recent AI News.
Video from today’s episode also at: youtube.com/calnewportmedia
0:00 Is AI About to Automate Every Office Job?
3:02 Other Tech Leaders Don’t Agree
5:49 -We Aren’t Seeing Enough Progress
14:09 -LLMS Are Limited
24:19 Conclusion
Links:
Buy Cal’s latest book, “Slow Productivity” at www.calnewport.com/slow
https://www.reddit.com/r/AI4t
How Do I Build “Cognitive Fitness”? | Monday Advice
In his recent New York Times essay, Cal argued for a “cognitive fitness” revolution to resist the onslaught of digital tools degrading our ability to think. But how does one actually strengthen their brain? In this episode, Cal details a sustainable cognitive fitness routine built around five key components.
Below are the questions covered in today's episode (with their timestamps). Get your q
Is AI Trending Up or Down in 2026? | AI Reality Check
Cal Newport takes a critical look at recent AI News.
Video from today’s episode: youtube.com/calnewportmedia
0:00 What has *Actually* Happened in AI in 2026?
3:07 Open Claw
27:53 Anthropic and the Department of War
49:06 Data Centers
Links:
Buy Cal’s latest book, “Slow Productivity” at www.calnewport.com/slow
https://www.axios.com/2026/01/31/ai-moltbook-human-need-tech
https://www
Do I Need More Discipline? | Monday Advice
Is developing discipline one of the most effective bulwarks against the constant flood of distraction we face daily? And if so, what’s the best way to accomplish this goal? In this Monday Advice episode of the show, Cal Newport investigates these questions with the help of Brad Stulberg, who writes about these ideas in his most recent book, the New York Times bestseller “The Way of Excellence.”
Is Claude Mythos “Terrifying”? | AI Reality Check
Cal Newport takes a critical look at recent AI News.
Today's episode on YouTube: youtube.com/calnewportmedia
0:00 What’s Really Going on with Mythos?
10:09 Security systems
21:27 Conclusion
Links:
Buy Cal’s latest book, “Slow Productivity” at www.calnewport.com/slow
https://www.youtube.com/watch?v=iRsycWRQrc8
https://www.nytimes.com/2026/04/07/opinion/anthropic-ai-claude-mythos.ht
Ep. 400: Should I Embrace “Slow Technology”?
Ep. 400: Should I Embrace “Slow Technology”?
If there was one word to describe modern digital tools, it would be “fast.” But not everyone thinks this is better. In today’s episode, Cal explores the concept of “slow technology” – the embrace of tools that have fewer features and more friction, but nonetheless produce better work and more satisfaction. His guide in this effort is the acclaimed chil
AI Reality Check: Is AI Stealing Entry-Level Jobs?
AI Reality Check: Is AI Stealing Entry-Level Jobs?
Cal Newport takes a critical look at recent AI News.
Video from today’s episode: youtube.com/calnewportmedia
OPENING: Is AI stealing entry-level jobs? [1:29]
MAIN STORY: Torsten Slok essay [3:06]
CONCLUSION: AI is not stealing entry-level jobs now [11:32]
Links:
Buy Cal’s latest book, “Slow Productivity” at www.calnewport.com/slow
https://
Ep. 399: Is Deep Work Still Possible in 2026?
It’s been a decade since the original publication of DEEP WORK. Do its ideas still hold in 2026? This is the question Cal tackles in today’s episode: reviewing the four major “rules” from his book, reviewing what still holds and what changes he would add.
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
AI Reality Check: Can LLMs “Scheme”?
Cal Newport takes a critical look at recent AI News.
Video from today’s episode: youtube.com/calnewportmedia
ACT #1: Look Closer at the Article [1:20]
ACT #2: A Closer Look at the Paper [3:21]
ACT #3: But What About… [7:24]
Links:
Buy Cal’s latest book, “Slow Productivity” at www.calnewport.com/slow
https://www.theguardian.com/technology/2026/mar/27/number-of-ai-chatbots-ignoring-human-inst
Ep. 398: How Do I Find Purpose in a Distracted World? (w/ Arthur Brooks)
Here’s a key question: Did technology like smartphones make us miserable, or were we already miserable and smartphones made it worse? To help figure out this answer, I talked to Arthur Brooks, the #1 New York Times bestselling author and Harvard professor, about this new book: The Meaning of Your Life: Finding Purpose in an Age of Emptiness. In our conversation, Brooks argues that our current Age
AI Reality Check: Are LLMs a Dead End?
Cal Newport takes a critical look at recent AI News.
Video from today’s episode: youtube.com/calnewportmedia
SUB QUESTION #1: What is Yan LeCun Up To? [2:55]
SUB QUESTION #2: How is it possible that LeCun could be right about LLM’s begin a dead-end? We’ve been hearing non-stop recently about how fast they’re advancing. [14:55]
SUB QUESTION #3: What would happen next if LeCun is right? [22:26]
Ep. 397: Why Do “Productivity Technologies” Make My Job Worse?
A new study finds that for many workers, AI increases shallow efforts while decreasing time focusing on what really matters. This is not the first digital productivity technology to create this paradoxical effect. In today’s episode, Cal dives deep into why this happens and then details three strategies for avoiding these traps in your own professional life.
Below are the questions covered in tod
AI Reality Check: Did AI Just Become Sentient?
Cal Newport takes a critical look at recent AI News.
Video from today’s episode: youtube.com/calnewportmedia
STORY #1: Did an AI Agent Email an AI Researcher? [1:01]
STORY #2: Does the Pentagon Think Claude Has a Soul? [10:20]
STORY #3: What’s Going on with Anthropic Revenues? [14:16]
Links:
Buy Cal’s latest book, “Slow Productivity” at www.calnewport.com/slow
https://futurism.com/artifici
Ep. 396: Can I Learn To Love My Phone Again?
Remember how much we loved our iPhones when they first came out? Can we get back to that relationship with these devices? In this episode, Cal explores five pieces of advice for transforming your current phone back to something that’s less distracting, more useful, and fun once again – a goal he calls “2007 mode.”
Below are the questions covered in today's episode (with their timestamps). Get you
AI Reality Check: Is the Economy About to Collapse?
Cal Newport takes a critical look at recent AI News.
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
ARTICLE #1: America Isn’t Ready for What AI Will Do to Jobs [2:15]
ARTICLE #2: Mass Hysteria. Thousands of Jobs Lost. Just How Bad Is
Ep. 395: Should I Try a “Social Media Pause”?
Do you need social media? Which services? For what purposes? These are complicated questions and in today’s episode Cal proposes a simple route to answers: conducting a “social media pause.” To help investigate this strategy, Cal is joined by T.K. Coleman, of The Minimalists, to talk about a social media pause that they tried and the surprising results it generated.
Below are the questions covere
AI Reality Check: Did the LLM Job Apocalypse Begin Last Week?
AI Reality Check: Did the LLM Job Apocalypse Begin Last Week?
Cal Newport takes a closer look at recent AI news.
Below are the topics 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
STORY #1: Jack Dorsey announces layoffs at Block [1:28]
STORY #2: The educat
Ep. 394: Do I Need a Better Planning System?
It’s hard to live deeply in a distracted world if you don’t have control over how you spend your time. This goal requires a planning system that both works and can last. Do you have a reasonable planning system in place? If not, don’t worry. Today, Cal is joined by planning expert Sarah Hart-Unger (author of “Best Laid Plans”) to discuss the nitty-gritty details of creating sustainable systems tha
Ep. 393: Can Movies Save Us From Our Phones?
Last month, the Atlantic reported that film students are now struggling to sit through entire films. In this episode, Cal argues that this is both an issue and an opportunity. The fact we can’t watch full movies indicates the impact of digital tools on our brains is worse than we assumed. But in this problem, we also find a solution: maybe teaching ourselves to become better movie watchers can be
Ep. 392: Are “Micro-Streamers” the Future of Media? + Why Cal Spent $60 on a Task App
There remains a gap between the production values of professional streaming services like Netflix and independent content that appears on platforms like YouTube. But what happens when that gap disappears? In the ideas segment of today’s episode, Cal sends a correspondent to investigate a fascinating new “micro-streaming” service producing Netflix-quality shows with a small team. Then, in the pract
Ep. 391: Is AI Reporting Broken? + Rethinking Morning Routines
Is there something rotten in the state of AI reporting at the moment? In the ideas segment of this episode, Cal details three common traps in AI coverage that distort or distract from the reality of this technology. Once you know what to look for, these traps become easy to avoid – greatly improving your experience when trying to keep up to date on the latest advancements. Then, in the practice se
Ep. 390: What Happens When You Ditch Your Smartphone? + Assessing the Internet’s Latest Self-Help Sensation
Everyone knows that excessive smartphone use can be harmful. But the question we don’t ask enough is what the advantages are of not using these devices. In the ideas segment, Cal examines the testimonials of four subjects who spent significant time without phones, to learn what they actually experience. Then, in the practices segment, he dissects the latest viral online self-help sensation to see
Ep. 389: Is the Internet Hijacking Ambition? + Escaping Messaging Hell
It’s natural to feel ambition, as we’re wired to find great satisfaction in accomplishing hard goals. But what impact has the internet had on this instinct? To help explore this question, author Brad Stulberg, author of the new book THE WAY OF EXCELLENCE, joins Cal during the ideas segment to explore ways in which the internet hijacks our drive, and what we can do about it. Then, in the practice s
Ep. 388: What’s Worrying Jon Haidt Now? + Should You Buy a Landline? (Cal just did…)
Despite some initial skepticism, Jonathan Haidt’s crusade against kids using smartphones has been more or less completely vindicated. Which got us thinking: what’s he worried about next? In the ideas segment, Cal looks closer at three new technological harms that Haidt has begun sounding the alarm about. Then, in the practices segment, he details a somewhat eccentric technology strategy that he an
Ep 387: Can Substack Save Journalism? + Viral Advice for Ignoring Your Phone
Last year, when columnist Paul Krugman left the NYT, it seemed like yet another example of the traditional media crumbling. But Krugman, as it turns out, is doing great. His popular substack now reaches massive audiences and earns him a seven-figure salary. Inspired by this story, in the ideas segment of today’s episode, we take a closer look at key numbers relevant to whether paid newsletters can
Ep 386: Was 2025 a Great or Terrible Year for AI? (w/ Ed Zitron)
Ep 386: Was 2025 a Great or Terrible Year for AI? (w/ Ed Zitron)
2025 was a year that was saturated in AI news, from Deep Seek, through claims of economic “bloodbaths,” to GPT-5, Sora, and Chatbot girlfriends. Frankly, it was exhausting. As we now look back on 2025 an interesting question arises: all in all, did this end up being a good or bad year for AI? To help me answer this question, I’m joi
Ep 385: Single-Purpose Notebooks (REPLAY)
In this replay of a classic episode from March 2024, Cal discusses his transformative experience using a small analog notebook to tackle a complicated problem in his life. He makes the broader argument that sometimes simple analog tools can far exceed the utility of their digital counterparts.
Below are the questions covered in today's episode (with their timestamps). Get your questions answered b
Ep 384: What Should I Read for a Deeper New Year?
In our annual holiday episode, Cal tackles one of the questions he’s asked most often: What should I read? But with a twist. He recommends six books that are not from the self-help or advice genre that will nonetheless help you change your life into something deeper. For the rest of the episode, he then answers listener calls.
Below are the questions covered in today's episode (with their timestam
Ep 383: Why Is Everyone Talking About “Against the Machine”? (w/ Tyler Austin Harper)
Earlier this fall, the activist, novelist, and essayist Paul Kingsnorth published an anti-technology polemic called “Against the Machine.” To say it hit a nerve is an understatement. In the months that followed, Kingsnorth has been everywhere; profiled, among places, in the New York Times, the New Yorker, and The Atlantic. In today’s episode, I want to find out why Kingsnorth’s take on technology
Ep. 382: Is the Internet Becoming Television?
Last month, Derek Thompson published an intriguing essay that made waves in technology criticism circles. It was titled: “Everything is Television.” In today’s episode, Cal takes a closer look at this essay, unpacking and expanding Thompson’s arguments, and ultimately concluding with a series of predictions about what to expect next from the internet. He then answers listener questions and discuss
Ep. Ep 381: Life Advice from Legendary Writers
In today’s episode, Cal reviews some of his favorite advice from legendary writers (plus a bonus piece of advice from his own craft). Within each suggestion, he finds a general idea that can apply to anyone looking to build a deep life in an increasingly distracted world. He then answers listener questions and responds to comments about last week’s episode.
Below are the questions covered in today
Ep. 380: ChatGPT is Not Alive!
There has been a lot of loose talk online recently about the capabilities of existing AI tools. In this episode, Cal reacts to a specific recent clip from the Joe Rogan podcast in which the guest argues that language models are like a child’s brain, and may already be conscious. Cal puts on his (always stylish) computer scientist had to explain why this cannot be true. He then answers listener que
Ep. 379: The Flexibility Myth
When companies began instituting return-to-office plans after the pandemic, a disproportionate number of women chose instead to leave the workforce. Why? The obvious answer is that they wanted the flexibility of remote work. But in this episode, Cal draws on a recent New York Times op-ed that offers a deeper explanation – one that affects all knowledge workers. He then explores solutions to the pr
Ep. 378: The Lost Art of Long Thinking
We often talk on this show about how digital devices undermine our ability to consume more complicated and meaningful ideas. But what about our ability to produce such ideas from scratch? In this episode, Cal identifies a key productive skill – long thinking – that we’re increasingly losing. He argues that it’s critical for living a deep life and provides a simple strategy to help regain the skil
Ep. 377: The Case Against Superintelligence
Techno-philosopher Eliezer Yudkowsky recently went on Ezra Klein's podcast to argue that if we continue on our path toward superintelligent AI, these machines will destroy humanity. In this episode, Cal responds to Yudkowsky’s argument point by point, concluding with a more general claim that these general styles of discussions suffer from what he calls “the philosopher’s fallacy,” and are distrac
Ep. 376: The Lincoln Protocol
How do you escape a world where constant digital distractions and darkness threatens to pull you down? Maybe take a page out of Abraham Lincoln’s life. In this episode, Cal argues that Lincoln faced analog versions of many of the same issues we face in our contemporary digital world, and by studying how he escaped we can learn a method to accomplish something similar. He then answers listener ques
Ep. 375: Did OpenAI Just Kill Social Media?
Ep. 375: Did OpenAI Just Kill Social Media?
OpenAI has been making waves recently with their release of their Sora 2 video generation model, which they have launched alongside a TikTok-style social media sharing app. The internet is usually pretty excited about AI innovations, but this one has people unsettled. In today’s episode, Cal looks at one implication of Sora 2 in particular that is both i
Ep. 374: This is Your Brain on Phones
It’s hard to cultivate a deep life when you cannot go more than a few minutes without checking your phone. In this episode, Cal looks closer at the precise neural mechanisms at play that make the physical act of looking at your phone irresistible. Then armed with this knowledge, he explains why many popular remedies fail, and which specific responses are most likely to succeed. He then answers lis
Ep. 373: The Internet’s Best Advice for Reinventing Your Life
In 2023, I published an episode about resetting your life that became one of my most popular. In the years since, multiple major podcasters and YouTubers have done their own videos on the same theme. In today’s episode, I extract the best ideas from five such recent videos to create an all-star reset strategy. I connect this to my work on technology and its impacts, by noting that taking control o
Ep. 372: Decoding TikTok’s Algorithm
Last week, it was announced that Oracle would take over operation of TikTok in the US. One of the primary reasons proposed for this deal is that it was in national interests for us to take over control of TikTok’s fabled “algorithm.” But what is this algorithm? How does it work? To what extent can it be controlled? In today’s episode, Cal looks deeper at these questions and arrives at a broader ph
IN-DEPTH: Focus like a Nobel Prize Winner (w/ Brian Keating)
In this episode of IN-DEPTH, Cal is joined by Dr. Brian Keating, the Chancellor’s Distinguished Professor of Physics at UCSD, and one of the most prolific popularizers of science around (you may have seen him recently chatting about cosmology with Joe Rogan and Andrew Huberman). They talk about Keating’s new book, HOW TO FOCUS LIKE A NOBEL PRIZE WINNER, as well as many other topics, including a de
Ep. 371: Is it Finally Time to Leave Social Media?
We seem to be stuck in a purgatory when it comes to the worst of the social media platforms. We know they’re not great, but it’s hard to muster enough motivation to bother to leave. In today’s episode, motivated by the assassination of Charlie Kirk, Cal puts on his technology critic hat and offers a step-by-step technical explanation for why these platforms are strictly and incessantly making your
Ep. 370: Deep Work in the Age of AI
A recent study called into question a core assumption about the generative AI revolution: that these tools, at the very least, will make us more productive. In this episode, Cal dives deep into the study and argues that when it comes to efforts that require deep work, AI can sometimes make things worse. He then answers listener questions and then takes a closer look at an article claiming that the
Ep. 369: Why Are We Getting Dumber? A Debate.
IQ scores had been steadily rising since WWII. But, more recently, this phenomenon has stopped. Since 2010, we’ve actually been getting dumber. In this episode, Cal gets into the common theories for why this is true before offering his own take, which leads to some practical takeaways to help you thrive in an increasingly stupider world. He then answers listener questions and talks about somethin
IN-DEPTH: The Game of Life (w/ Tim Ferriss)
In this episode of IN-DEPTH, Cal is joined by bestselling author and podcaster, Tim Ferriss. Tim rocketed to prominence with his 2007 book, “The Four Hour WorkWeek” which basically redefined a generation’s relationship with work, meaning, and the possibilities for building an interesting life. More recently, Tim created a card game! It’s called Coyote. And he created it with one of the top designe
Ep. 368: I Want Work-Life Balance. Am I Doomed to Mediocrity?
A 22-year-old made a splash recently when he published a Wall Street Journal op-ed claiming that work-life balance makes you mediocre. He went on to brag about how sleeping less than 4 hours a night and gaining 80 pounds helped him become a millionaire. In this episode, Cal wades into the furious debate this article sparked. He argues that once you look past the author’s dorm bro bravado, the kid
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