Taylor Pearson: "The End of Jobs," History, and Navigating Uncertainty

Please welcome my friend Taylor Pearson to the show. Taylor is a fellow father and entrepreneur, the author of The End of Jobs, an essayist with his Interesting Times newsletter, a fellow Tennessean, one of the founders of a long-volatility and tail-risk hedge fund, and a former college football player, where he played offensive line. He's spent the last decade researching and writing about how you can better invest your time and money in an uncertain world, i.e., how to be more antifragile.

Welcome, Taylor.

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💬 Taylor Pearson Quotes From the Episode
"Reality has a surprising amount of detail."

"You don't have 100% agency over everything, but you almost might as well act as if you do. The things you don't have control over... You just have to chalk those up to trade-offs. Like you can't do this, you can't do that, fine, fair enough. Within the possibility space, 'What can you do?' And I still catch myself, not infrequently, saying that, 'Oh, I could do this actually.' "

"My basic thesis was that we're going through this transitional period where entrepreneurialism, not necessarily starting a business, but thinking more entrepreneurially about your career life, was going to become increasingly important."

🔗 Additional Resources
Taylor Pearson: https://taylorpearson.me/
Taylor Pearson on X: https://x.com/taylorpearsonme
Taylor Pearson on LinkedIn: https://www.linkedin.com/in/ctaylormpearson/
"The End of Jobs" by Taylor Pearson: https://www.amazon.com/End-Jobs-Meaning-9-5-ebook/dp/B010L8SYRG
"Systemantics: The Systems Bible" by John Gall: https://www.amazon.com/SYSTEMANTICS-SYSTEMS-BIBLE-John-Gall-ebook/dp/B00AK1BIDM
"Understanding Media: The Extensions of Man" by Marshall McLuhan: https://www.amazon.com/Understanding-Media-Extensions-Marshall-McLuhan/dp/0262631598
"The Snowball: Warren Buffett and the Business of Life" by Alice Schroeder: https://www.amazon.com/Snowball-Warren-Buffett-Business-Life/dp/0553384619

📝 Show Notes
02:45 – Taylor on Discovering Agency While Teaching in Brazil
05:10 – Embracing Responsibility and Trade-Offs
09:24 – The Core Message Behind The End of Jobs
10:38 – The Rise of Internet Careers from a 2011 Perspective
14:30 – Golf as a Meditative Recharging Tool
15:20 – Why Biographies Are the Best Way to Learn History
18:07 – How AI and Museums Are Changing How We Learn History
22:00 – What College Taught Taylor About Interpreting History
28:51 – Taylor’s Bias: Technology as the Driver of History
35:27 – “Reality Has a Surprising Amount of Detail”
36:25 – Tolstoy, War, and the Myth of the Great Man
47:08 – Why Systems Fail: Lessons from Systemantics
53:38 – Unintended Consequences: Lessons from Vietnam and Beyond
55:30 – How to Get in Touch With Taylor via His Interesting Times Newsletter

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#futureofwork #historymatters #entrepreneurship