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
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 questions co
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
Ep. 367: What if AI Doesn’t Get Much Better Than This?
In recent years, it’s been hard not to react to the possibilities of generative AI without a mixture of euphoria or dread. But after OpenAI’s lackluster GPT-5 launch, a new, almost heretical-seeming question has emerged: what if progress on AI is stalled well short of the wild predictions we were promised? In today’s episode, Cal draws from reporting on his recent New Yorker article to go deep int
Ep. 366: How to Reinvent Your Life in 4 Months (Classic Episode from August, 2023)
In this replay of one of the more popular episodes from the Deep Questions archives, originally aired in August ,2023, Cal explores some of his early strategies for cultivating a deeper life.
Below are the questions covered in today's episode (with their timestamps). Get your questions answered by Cal! Here’s the link: bit.ly/3U3sTvo
Today’s Deep Question: How can I reinvent my life in 4 months? [
Ep. 365: What Technology Wants (and How to Push Back)
Why do we end up entangled with tools that don’t have our best interests in mind? How can we fix this situation? In this episode, Cal dives deep into the difference between additive and extractive technologies, telling a story that weaves old technology with old versions of modern tools, testimony from recent trials to ideas from leading technology critics – all in the service of improving your re
Ep. 364: Metrics 101
When Cal recently returned home from his time spent up in New England he set up a whole new set of daily metrics to track in the fall to keep him pointed toward the deep life. And they failed. Hard. In this episode, Cal dissects why metrics matter, why they’re easy to mess up (including the mistakes he made), and how to use them correctly (including how he corrected his own setup). He then answers
Ep. 363: Escaping the Digital Doldrums
What does Walt Disney’s malaise in the 1940s have to do with our current struggles with our screens? In this episode, Cal uses a little-known story from Disney’s midlife to identify an effective strategy for escaping the nerve-deadening, dull state created by spending more and more of your professional and personal life on screens. He then answers listener questions (with an unusual level of spici
Ep. 362: The Texting Dilemma
When we think about unhealthy phone usage, we think about the flashing apps, like TikTok and Instagram, in which billions of dollars have been spent to grab our attention. In this episode, Cal points to an unassuming culprit that may be just as responsible: simple messaging apps. He explores research that connects the social stress of pending messages to phone addiction, and explores ways to free
Ep. 361: Do You Need an App Blocker?
Are you worried that you’re using your phone too much? An app blocker might make sense. But how do they work, and which one is right for you? In this episode, Cal goes deep into the motivation, technology, and ultimate end game of this distraction fighting technology. He then answers listener questions and discusses some intriguing comments he’s been seeing about limits to AI’s ability to code.
Be
Ep. 360: One-Page Productivity
Trying to stick to complicated time management systems without any breaks can eventually lead to burn out. But if you stop organizational efforts altogether, your life can become a stressful mess. In this episode, Cal taps the wisdom of an elite running coach to devise what he calls one-page productivity: a minimum time management system, meant to be run for limited periods to help you recharge, b
Ep. 359: Should We Fear Cognitive Debt?
A blockbuster new study out of MIT takes a closer look at the impact of writing with the help of AI. In today’s episode, Cal breaks down this paper with the help of author Brad Stulberg (who made waves online recently with his reaction to its findings), picking apart the role of AI in deep work activities. Cal then answers listeners questions, and presents a twist on his typical final segment in w
Ep. 358: Are Parents (Finally) Ready to Fight Smartphones?
Back in 2023, Cal gave a detailed deep dive that described the three phases of scientific understanding of smartphones, social media, and kids. In today’s episode, Cal argues that we’ve entered a fourth phase; one that will finally lead to (perhaps rapid) cultural changes about what we think is appropriate when it comes to these tools and kids. He then answers listener questions and describes a re
Ep. 357: What Worries the Internet’s Favorite Philosopher?
Few philosophers in recent memory have enjoyed as much attention as Byung-Chul Han. His mix of profundity and pithiness in tackling some of the big issues of the modern technical environment has made him “the internet’s new favorite philosopher” (to quote The New Yorker). But is he saying that is making such an impact? In this episode, Cal seeks to find out. He reports back on five of the biggest
IN-DEPTH: The Art of Non-Conformity (w/ Chris Guillebeau)
In this episode of IN-DEPTH, Cal is joined by Chris Guillebeau, the author of the new book, TIME ANXIETY, and creator of the beloved Art of Non-Conformity blog and World Domination Summit annual conferences. Cal and Chris reminisce about their old days as early advice bloggers and dive into his new ideas about re-thinking our relationship with time.
Video from today’s episode: youtube.com/calnew
Ep. 356: How Much Should We Work?
The data shows knowledge workers really are more exhausted and more prone to burnout than ever before. But why? In this episode, Cal draws inspiration from an unlikely source to help unpack this troubling trend and then suggest a perhaps radical solution. He then answers listeners’ questions and discusses his latest New Yorker article on the challenges of taming AI. As a bonus, he briefly discusse
Ep. 355: Quit Social Media (For Real This Time)
A common complaint about social media skepticism is that we’re falling into a classic moral panic. We’ve been concerned about many past mass media technologies, and ultimately came to realize that they’re not so bad. So why would we expect anything different about social media? In this episode, Cal tackles this complaint, drawing on an unexpected analogy to find clarity. He then answers listener q
Ep. 354: The Workload Fairytale
A few years ago, in a spirit of post-pandemic experimentation, multiple countries ran formal trials to test a radical idea: shortening the workweek. In this episode, Cal returns to the results of these trials to identify an astounding finding that has critical implications about how we work in the 21st century and how this could be made much better. He then answers listener questions and concludes
Ep. 353: Summer Schedules
Summer is here. It’s time to slow down. In this episode, Cal discusses his radically simplified summer schedule and then suggests you similarly inject some “seasonality” into your life, offering tips for finding a slower gear without tanking your job. He then answers listener questions and reacts to the most important AI article that you likely missed last week.
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Ep. 352: It’s Okay to Slow Down
When we think about important accomplishments, we think about grinding through long hours of work. But is this really necessary? In this episode, Cal turns to the lives of two famous authors to argue that sometimes a slow and steady approach can work just as well in the end, while making the journey more sustainable along the way. He then answers listener questions and concludes with a Tech Corner
Ep. 351: Making the Internet Good Again
Tyler Cowen recently wrote an article arguing that spending lots of time online is in fact a good thing. In this episode, Cal looks deeper at Cowen’s argument and finds some surprising common ground. The internet can be a major source of good in your life, he argues, but only if you use it in the right way. He then answers listener questions and reviews the books he read in April.
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