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 into this question. What is going on with AI? How did we get here? What does it mean for our personal quest to live deeper lives? He then answers listener questions and ends by discussing his recent brush with literary acclaim.

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

Video from today’s episode: youtube.com/calnewportmedia

Deep Dive: What if AI Doesn’t Get Much Better Than This? [1:00]

• Will AI leave me unemployed in 10 years? [1:06:26]
• How should I structure the next 10 years as a recently retired college professor? [1:13:58]
• I just moved. How should I arrange my book collection? [1:15:36]

CALL: Overhead tax [1:17:47]

CAL REACTS: Ed Sheehan and the Booker Prize [1:27:55]

Links:

Buy Cal’s latest book, “Slow Productivity” at www.calnewport.com/slow
Get a signed copy of Cal’s “Slow Productivity” at peoplesbooktakoma.com/event/cal-newport/
Cal’s monthly book directory: bramses.notion.site/059db2641def4a88988b4d2cee4657ba?
newyorker.com/culture/open-questions/what-if-ai-doesnt-get-much-better-than-this
youtube.com/watch?v=zju51INmW7U
youtube.com/watch?v=Dtdue31z-X8
youtube.com/watch?v=0SXCIfFK5r8
youtube.com/shorts/dYZmGHOLNRU
youtube.com/watch?v=k82RwXqZHY8
youtube.com/watch?v=qhnJDDX2hhU
youtube.com/watch?v=qbIk7-JPB2c&t=3s
youtube.com/watch?v=k82RwXqZHY8
youtube.com/shorts/JCImeOUVTJE

Thanks to our Sponsors:

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Thanks to Jesse Miller for production, Jay Kerstens for the intro music, and Mark Miles for mastering.

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? [1:30]

• How can I ease into Cal's more advanced time management strategies? [36:58]
• Can unstructured work be a part of the deep life? [40:33]
• How can I stop changing my mind about what I want to do with my life? [44:41]
• Can I pursue the deep life if I need a job? [52:24]
• How do you pursue the deep life with depression? [56:49]

Cover Reveal for Slow Productivity [1:05:27]

Thanks to our Sponsors:

This show is brought to you by Better Help.

https://www.betterhelp.com/deepquestions

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https://www.shopify.com/deep

Thanks to Jesse Miller for production, Jay Kerstens for the intro music, and Mark Miles for mastering.

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 relationship with tools. He then answers listener questions and discusses the books he read in July, 2025.

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

Deep Dive: What Technology Wants (and How to Push Back) [:54]
- Do project trackers work? [34:54]
- Is there a downside scenario to engineering wonder? [39:14]
- What types of people should I surround myself with? [43:00]
- Can you explain your different audiences? [45:02]

CALL: Shifting from medical work to a PhD [50:41]
JULY BOOKS: The 5 Books that Cal Read in July, 2025 [57:33]

L.A. Story (Bill Plunkett)
Disney’s Land (Richard Snow)
Ingenious (Richard Munson)
Original Sin (Jake Tapper and Alex Thompson)
Wool (Hugh Howey)

Links:
Buy Cal’s latest book, “Slow Productivity” at www.calnewport.com/slow
Get a signed copy of Cal’s “Slow Productivity” at https://peoplesbooktakoma.com/event/cal-newport/
Cal’s monthly book directory: bramses.notion.site/059db2641def4a88988b4d2cee4657ba?
https://substack.com/@priscillaharvey1/note/c-133662492
https://www.yahoo.com/news/zuckerberg-tells-court-facebook-no-171222971.html
https://www.vanityfair.com/news/story/mark-zuckerberg-is-so-over-facebook-friends?srsltid=AfmBOoo4dysXG_2rXWDJaKnSdG6CfbCqf0O_8op_R1phpz5GQPx2F4XA
https://www.youtube.com/watch?v=R7jar4KgKxs
https://pluralistic.net/2022/11/28/enshittification/
https://www.youtube.com/watch?v=_Ai-fC-2Bpo
https://www.emarketer.com/content/openai-hires-its-first-cmo-kate-rouch-foreshadowing-ads
https://www.youtube.com/watch?v=qfUpEWAKPf8&t=2350s

Thanks to our Sponsors:
https://www.expressvpn.com/deep
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Thanks to Jesse Miller for production, Jay Kerstens for the intro music, and Mark Miles for mastering.

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 listener questions and discusses a recent AI article that got him all hot and bothered.

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

Video from today’s episode: youtube.com/calnewportmedia

Deep Dive: Metrics 101 [2:10]

• How should I navigate the “grey area” when deciding to make a career change? [24:45]
• Do you have a framework for young people to develop deep critical thinking? [27:36]
• What should a father of 4 kids do for his next career move? [32:34]
• Can skills from a high-pressure call center carry over to a career in cybersecurity? [35:36]
• Should I have anticipated that my job was going to end? [38:36]

CALL: Returning back to work after a summer break [43:14]

CASE STUDY: Pursuing a hobby while combating digital doldrums [46:47]

WHAT I’M (NOT) READING: Vibe Reporting on AI [55:52]

Links:

Buy Cal’s latest book, “Slow Productivity” at calnewport.com/slow
Get a signed copy of Cal’s “Slow Productivity” at peoplesbooktakoma.com/event/cal-newport/
Cal’s monthly book directory: bramses.notion.site/059db2641def4a88988b4d2cee4657ba?
nytimes.com/2025/07/28/arts/video-games-artificial-intelligence.html

Thanks to our Sponsors:

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Thanks to Jesse Miller for production, Jay Kerstens for the intro music, Kieron Rees for segment music, and Mark Miles for mastering.

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 spiciness), tries to calm himself with a reprise of the SLOW PRODUCTIVITY CORNER theme music, and concludes with a discussion of a recent essay he wrote about how no one really knows anything about AI.

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

Video from today’s episode: youtube.com/calnewportmedia

Deep Dive: [1:47]

• How should I pursue two different goals after leaving my software engineering career? [21:10]
• Should I leave my business analyst job and buy a retail business? [24:32]
• I’ve tried writing for editors (and publications) before with no success. Any suggestions on how to break through? [30:08]
• How do I convince my company that AI assistance is not the answer? [35:27]
• Is inspiration perishable like Naval Ravikant says? [38:11]

CALL: Inbox anxiety [43:15]

CASE STUDY: A public school teacher with a blog [51:27]

WHAT I’M WRITING: No One Knows Anything About AI [59:13]

Links:

Buy Cal’s latest book, “Slow Productivity” at calnewport.com/slow
Get a signed copy of Cal’s “Slow Productivity” at peoplesbooktakoma.com/event/cal-newport/
Cal’s monthly book directory: bramses.notion.site/059db2641def4a88988b4d2cee4657ba?
amusingplanet.com/2019/01/walt-disneys-backyard-railway-carolwood.html
youtu.be/KyfUysrNaco?si=uE6tJkPuFhdnbla2&t=2490
calnewport.com/no-one-knows-anything-about-ai/

Thanks to our Sponsors:

drinklmnt.com/deep
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Thanks to Jesse Miller for production, Jay Kerstens for the intro music, and Mark Miles for mastering.

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 yourself from constant messaging without having to isolate yourself socially. He then answers listener questions and discusses what he’s been reading.

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

Video from today’s episode: youtube.com/calnewportmedia

Deep Dive: The Texting Dilemma [5:35]

• How can I structure my mornings with my sales job if I don’t have two hours for deep work? [31:44]
• How should I handle mandatory overtime at my aerospace job? [33:18]
• How can I handle too many open loops with my shutdown ritual? [35:54]
• How can I better organize communication with my university students? [40:38]
• Should I take on extra-curricular roles during my first year of my PhD? [44:00]

CALL: Household chore task list [48:01]

CASE STUDY: 30-day declutter [51:45]

WHAT TO READ: An author quits social media [59:45]

Links:

Buy Cal’s latest book, “Slow Productivity” at calnewport.com/slow
Get a signed copy of Cal’s “Slow Productivity” at peoplesbooktakoma.com/event/cal-newport/Cal’s monthly book directory: bramses.notion.site/059db2641def4a88988b4d2cee4657ba?
sciencedirect.com/science/article/abs/pii/S0747563214007626
journals.uchicago.edu/doi/10.1086/691462
pmc.ncbi.nlm.nih.gov/articles/PMC9671478/
carolinecrampton.com/im-done-with-social-media/

Thanks to our Sponsors:

calderalab.com/deep
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grammarly.com/podcast

Thanks to Jesse Miller for production, Jay Kerstens for the intro music, and Mark Miles for mastering.

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.

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

Video from today’s episode: youtube.com/calnewportmedia

Deep Dive: Do You Need an App Blocker? [4:35]

- How do I succeed with task management? [29:07]
- How can I put boundaries on my administrative work for my university job? [33:58]
- How should I manage X if I only use it on my desktop? [39:31]
- How should I read through my weekly collection of newsletters? [41:11]
- What do you think about Polyphasic sleep to prepare for deep work? [44:22]

CASE STUDY: A ticketing system in action [45:21]

WHAT TO READ: On the Limits of “Vibe Coding” [50:58]

Links:

Buy Cal’s latest book, “Slow Productivity” at calnewport.com/slow
Get a signed copy of Cal’s “Slow Productivity” at peoplesbooktakoma.com/event/cal-newport
Cal’s monthly book directory: bramses.notion.site/059db2641def4a88988b4d2cee4657ba?
sciencefocus.com/science/youre-not-actually-addicted-to-your-smartphone
nytimes.com/2020/01/20/style/quit-smartphone.html
support.apple.com/guide/iphone/get-started-with-screen-time-iphbfa595995/ios
youtu.be/OuizzRCALCU?si=FqHzEEFdq7k4ao13
x.com/AglaiaCodes/status/1942636133248061590
x.com/GaryMarcus/status/1942478390323552588/photo/1

Thanks to our Sponsors:

This show is sponsored by BetterHelp:
betterhelp.com/deepquestions
mybodytutor.com
expressvpn.com/deep
indeed.com/deep

Thanks to Jesse Miller for production, Jay Kerstens for the intro music, and Mark Miles for mastering.

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, but that also maintains just enough organization that you can avoid disaster. He argues such maintenance modes should be an important part of any time management practice. Cal then answers listener questions and concludes by reviewing the books he read in June 2025.

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

Video from today’s episode: youtube.com/calnewportmedia

Deep Dive: One-Page Productivity [1:52]

• How do you approach decisions when you’re torn between two reasonable options? [18:17]
• How can I navigate teaching with phone addicted teenagers? [22:06]
• Have you considered using LLM’s to assist in your writing? [28:03]
• How many “thinking” walks do you take each week? [32:31]
• Do you have any recommendations for learning new material outside of the structured framework of a course? [35:00]

CASE STUDY: A son explains his parents lifestyle engineering [37:21]

CALL: Setting up workflows as a manager [41:09]

JUNE BOOKS: The 5 Books Cal Read in June, 2025 [52:05]

• The Magic of Code (Samuel Arbesman)
• In the Swarm (Byung-Chul Han)
• The Fear Index (Robert Harriss)
• The Explore’s Gene (Alex Hutchinson)
• Skywalking (Dale Pollock)

Links:

Buy Cal’s latest book, “Slow Productivity” at calnewport.com/slow
Get a signed copy of Cal’s “Slow Productivity” at peoplesbooktakoma.com/event/cal-newport/
Cal’s monthly book directory: bramses.notion.site/059db2641def4a88988b4d2cee4657ba?
nytimes.com/athletic/6453809/2025/06/27/bruce-bochy-walking-exercise-creativity/

Thanks to our Sponsors:

cozyearth.com (Use code “DEEP”)
oracle.com/deepquestions
vanta.com/deepquestions
shopify.com/deep

Thanks to Jesse Miller for production, Jay Kerstens for the intro music, and Mark Miles for mastering.