31 Lessons I’ve Learned About Money

Ryan Holiday
10 min readMay 17, 2023

I remember learning how to play the recorder in elementary school. I remember square dancing. I remember cursive. I built a model of a Spanish mission out of sugar cubes.

Some of this was fun. Some of it wasn’t. Some of it probably contributed, in some indirect way, to my general ability to learn and function in the world. Most of it, I think it’s safe to say, did not.

Something I don’t remember learning about at all? Money. Even our math problems were mostly about potatoes and trains, not how to calculate the interest rate on credit cards or the return on an investment. There was the occasional — and now very politically incorrect — remark from teachers about how if you didn’t do well in school, you’d end up working at McDonalds. But even with all the pressure to go to college, school provided very little in the way of discussion about what kind of careers paid what, how to live within one’s means whatever that career was, let alone how one might create their own business and work for themselves.

This is sad and strange and hardly rare. We leave it to kids who become adults who then have kids to just figure it out for themselves. Not everyone does. I’ve since met high income earners who were terrible with money. I’ve met people who were quite rich by every financial metric but whose relationship with that money was quite terrible, (you’d never want to trade places with them). I’ve met people who have been the victims of scams and frauds because they lacked the basic knowledge needed to protect themselves.

To the Stoics, the solution to these timeless problems — the way to be better with money, to improve your relationship with money, to not fall for every smooth talker, Marcus Aurelius said — is the same: get smarter. Become better educated on the topic of money. “Wisdom,” as Seneca said, “offers wealth in ready money.” It’s something I’ve been thinking a lot about in my own journey — growing up with two civil servant parents, dropping out of college, succeeding in the corporate world until I dropped out of that as well to work for myself. I’ve been thinking about it a lot now that I have kids.

And I’ve been thinking about it a lot in researching and writing what is the most in-depth course ever built over at Daily Stoic: The Wealthy Stoic. It’s a 9-week course

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Ryan Holiday

Bestselling author of ‘Conspiracy,’ ‘Ego is the Enemy’ & ‘The Obstacle Is The Way’ http://amzn.to/24qKRWR