Deep Questions with Cal Newport

Am I Optimizing Too Much? | Monday Advice

Deep Questions with Cal Newport

Show Notes

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 Brad Stulberg

(35:12) Health optimization

(1:09:16) Tail end development

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?

Thanks to our Sponsors:

https://wealthfront.com/deep

https://calderalab.com/deep

https://cozyearth.com (Use code “DEEP”)

Cal Newport is not a Wealthfront client.

Wealthfront’s high-yield cash account: ⁠https://www.wealthfront.com/deep⁠. This experience may not be representative of other Wealthfront clients, and there is no guarantee of future performance or success. Experiences will vary. Cal Newport receives cash compensation from Wealthfront Brokerage for paid endorsement in his podcast, creating a conflict of interest. The Cash Account, which is not a deposit account, is offered by Wealthfront Brokerage LLC, member FINRA/SIPC. Wealthfront Brokerage is not a bank. The base APY is 3.30% on cash deposits as of January 30, 2026, is representative, subject to change, and requires no minimum. If eligible for the overall boosted rate of 4.05% offered in connection with this promo, your boosted rate is also subject to change if the base rate decreases during the 3 month promo period. Additional terms and conditions apply, which can be found on ⁠wealthfront.com/deep⁠. Funds in the Cash Account are swept to program banks, where it earns the variable APY. Investment advisory services are provided by Wealthfront Advisers LLC, an SEC-registered investment adviser. Securities investments: not bank deposits, bank-guaranteed or FDIC-insured, and may lose value.

Thanks to Jesse Miller for production and mastering, Jay Kerstens for the intro music, and Nate Mechler for research and newsletter.

Learn more about your ad choices. Visit podcastchoices.com/adchoices

More from Deep Questions with Cal Newport

Oct 22, 2026

Tesla’s recent demo of a rocket-powered Roadster doing a kick-flick over a parked car touched a nerve in me. It seemed to epitomize changes to the tech sector in recent years that have been largely negative. In this short episode, I jump on the mic to explain some of my developing thoughts surrounding these ideas.

Oct 19, 2026

A lot of attention has been paid recently to examples of AI going “rogue.” What’s missing from this discussion, however, is a more detailed explanation of what specific types of systems are causing problems. Taking a closer look at this problem reveals an issue that’s much more narrow and much more avoidable than some of the frontier labs would like you to believe.

Oct 12, 2026

How do we stop from becoming so reliant on LLMs that we lose our ability to think. A new paper explores answers based on an unlikely source: rigorous mathematical models. In this episode, Cal explains the paper and its conclusions, arguing that once you cut through its complexity it yields a useful way of thinking about our current AI moment.

Oct 8, 2026

Cal Newport takes a critical look at recent AI News. Cal interviews Emile Torres who provides a stark warning about AI.

Oct 5, 2026

One of the more debilitating experiences in our current digital world is the sense of being trapped in relentless, reactive, busyness. This “whirlwind” can separate you from both ambition and presence, leaving you feeling flat and fried. In this episode, Cal discusses a simple trick he deploys when he finds himself in this state. It requires only a single sheet of paper.

See all episodes →