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/calnewportmedia

INTERVIEW: The Art of Non-Conformity (w/ Chris Guillebeau) [03:50]

Links:
https://www.calnewport.com/slow

Sponsors:
https://www.donedaily.com

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

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 discusses Cal Network’s new bestselling book.

Find out more about Done Daily at DoneDaily.com!

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: How Much Should We Work? [3:33]

- What’s your advice on having a career backup plan? [28:27]
- Do you know of any executive coaches who teach your principles? [30:33]
- Is my retirement plan too ambitious? [35:13]
- Are accountability support tools acceptable to use in order to build discipline? [38:43]
- How can I identify if I have an inventory of "rare and valuable skills"? [41:21]

CASE STUDY: Crafting a storytelling profession [43:14]

CALL: Creating a life dashboard [46:14]

TECH CORNER: Why Can’t We Tame AI? (Cal’s latest New Yorker article) [52:08]

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?
newyorker.com/culture/open-questions/what-isaac-asimov-reveals-about-living-with-ai

Thanks to our Sponsors:

drinklmnt.com/deep
oracle.com/deepquestions
indeed.com/deep
vanta.com/deepquestions

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

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 questions and discusses the books he read in May, but not before first confronting a truly bizarre (or, perhaps, brilliant) piece of art work created by a fan of the show.

Find out more about Done Daily at DoneDaily.com!

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: Quit Social Media [6:18]

- How can I become a better, more analytical thinker? [23:04]
- How can I stay motivated, productive, and balanced while working mostly alone during my first remote internship? [28:56]
- How much time should I dedicate to developing secondary skills? [30:10]
- How does TikTok seem to know so much about me? [32:09]
- What are the best workflow strategies when using AI agents? [43:45]

CASE STUDY: A simple, analog approach to productivity [49:31]

CALL: Too focused on metrics [53:15]

MAY BOOKS: The 5 Books Cal Read in May 2025 [1:03:19]

May Books:

• Building: A Carpenter’s Notes on Life & the Art of Good Work (Mark Ellison)
• Thoreau’s Axe (Caleb Smith)
• 9 Innings (Daniel Okrent)
• Let Them (Mel Robbins)
• Against the Machine (Paul Kingsnorth)

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?
amazon.com/Four-Days-Week-Life-Changing-Well-Being/dp/0063382431/r
calnewport.com/on-ultra-processed-content/
podcasts.apple.com/us/podcast/cal-newport-5-28-19/id814550071?i=1000647135862
rehearsal.so/blog/how_to_stay_in_flow_while_using_cursor_or_windsurf

Thanks to our Sponsors:

cozyearth.com/deep
shopify.com/deep
harrys.com/deep
calderalab.com/deep

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