37 Pieces of Career Advice I Wish I’d Known Earlier

Ryan Holiday
11 min readFeb 21, 2024
From my first desk job working at my college newspaper.

My first job was working at a small deli and grocery store in Lake Tahoe when I was 15. It was a job that came full circle some twenty years later when my wife and I bought a place called ​Tracy’s Drive-In Grocery​ in 2021, a little place that’s been in business since 1940.

I’ve had my fair share of gigs in between.

I worked in fast food. I was the director of marketing for a publicly traded company. I’ve been a lifeguard. I dropped out of college to be a research assistant to an author. I worked a desk at a talent agency in Beverly Hills. I’ve started multiple businesses. I’ve freelanced. I’ve been lucky enough to speak and consult with multi-billion dollar companies and Super Bowl winning sports franchises, family offices and law firms.

I wouldn’t say I’ve done it all because that’s one thing you learn–how much you have left to learn–but I have done a lot. I’ve had to think a lot about how to be a good employee as well as how to be a good boss. I’ve seen what makes good companies succeed and bad companies fail. I’ve seen how people get ahead…and how people get stuff.

I’ve also written a lot about this over the years, as I was figuring it out. In fact, many times I had to talk to bosses about this “little thing I do on the side” which was writing until eventually, the business stuff itself because of the stuff I do on the side. And now I have to have the conversation the other way with the people who work for me at ​Daily Stoic​ or ​Brass Check​ or at ​The Painted Porch​ or at ​Tracy’s​: Ok, but what do you really want to do and how can I help you get there?

Anyway, this post is about that. The best of those lessons — things I wish I’d been told when I was just starting and things I still tell myself. Some of them might be exactly what you need to hear right now. Some might not apply to you yet, or ever. That’s okay. Whether you’re just starting out, looking to make a big change, or aiming to reach new heights in your current role, I hope you’ll find something here that helps you navigate your own unique path.

  1. Be quiet, work hard, and stay healthy. It’s not ambition or skill that is going to set you apart but sanity.
  2. I remember once I called Dov Charney, founder of American Apparel…



Ryan Holiday

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