143: Why Playing It Safe Could Be the Riskiest Career Move (ft. Taylor Pearson)

David speaks with Taylor Pearson, an author, investor, and principal at Mutiny Fund. Taylor wrote The End of Jobs, a book about how work is changing and what that means for people building their careers today. These days, he focuses on decision-making, risk, and helping investors think about uncertainty through his work at Mutiny Fund.

They talked about:

📚 How ditching plans to become a lawyer changed Taylor's life

⚠️ How "safe" career paths often hide the biggest risks

💼 Why some jobs will feel secure until they aren't

🔒 Why job security and career stability are not the same thing

🧾 How to track your life balance sheet beyond money

🧠 How thinking like an investor can help with making smarter life choices

📜 Full transcript:

https://theknowledge.io/taylorpearson-3/

📹 Watch on Youtube:

https://youtu.be/ntz5LnTzez8

🗣 Mentioned in the show:

Paul Graham | http://www.paulgraham.com/

Paul Millerd | https://theknowledge.io/paulmillerd/

Nassim Taleb | https://www.fooledbyrandomness.com/

Naval Ravikant | https://theknowledge.io/conquering-comfort-two-razors-from-naval-to-sharpen-your-choices/

Luca Dellanna | https://theknowledge.io/lucadellana-1/

Charlie Munger | https://theknowledge.io/can-you-beat-your-opponent-in-their-own-game-mungers-law-and-the-art-of-the-steelman/

Elon Musk | https://theknowledge.io/elons-law-beating-hofstadters-law-with-ridiculous-deadlines/

Brian Eno | https://www.enoshop.co.uk/

Kevin Kelly | https://kk.org/

Venkatesh Rao | https://www.ribbonfarm.com/about/

Douglas Adams | http://www.douglasadams.com/

Mutiny Fund | https://mutinyfund.com/

IBM | https://www.ibm.com/

Amazon | https://www.amazon.com/

Amazon Web Services (AWS) | https://aws.amazon.com/

Wells Fargo | https://www.wellsfargo.com/

Y Combinator | https://www.ycombinator.com/

Netflix | https://www.netflix.com/

Hallmark | https://www.hallmark.com/

OpenAI | https://openai.com/

Google | https://www.google.com/

Facebook | https://www.facebook.com/

Apple | https://www.apple.com/

Scribe Media (formerly Book in a Box) | https://scribemedia.com/

Toyota | https://www.toyota.com/

Minnesota Vikings (NFL) | https://www.vikings.com/

Dallas Cowboys (NFL) | https://www.dallascowboys.com/

The End of Jobs | https://theknowledge.io/taylorpearson-2/

Fooled by Randomness | https://www.amazon.com/Fooled-Randomness-Hidden-Chance-Markets/dp/0812975219

The Black Swan | https://www.amazon.com/Black-Swan-Impact-Highly-Improbable/dp/081297381X

Antifragile | https://theknowledge.io/reimaging-work-life-balance/

The Pathless Path | https://theknowledge.io/paulmillerd/

Flatland | https://www.amazon.com/Flatland-Romance-Many-Dimensions-Dover/dp/048627263X

The Hitchhiker’s Guide to the Galaxy | https://www.amazon.com/Hitchhikers-Guide-Galaxy-Douglas-Adams/dp/0345391802

Snow Crash | https://www.amazon.com/Snow-Crash-Novel-Neal-Stephenson/dp/0553380958

The Almanack of Naval Ravikant | https://www.amazon.com/Almanack-Naval-Ravikant-Wealth-Happiness/dp/1544514212

Wealth – essay by Paul Graham | http://www.paulgraham.com/wealth.html

👤 Connect with Taylor:

Twitter: https://x.com/TaylorPearsonMe

Website: taylorpearson.me

👨🏾‍💻 About David Elikwu:

David Elikwu FRSA is a serial entrepreneur, strategist, and writer. David is the founder of The Knowledge, a platform helping people think deeper and work smarter.

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