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:

grammarly.com/podcast
cozyearth.com/deep
calderalab.com/deep
shipstation.com/deep

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

https://www.mybodytutor.com

https://www.miro.com

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
https://www.oracle.com/deepquestions
https://www.indeed.com/deep
https://www.calderalab.com/deep

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