23 pieces of career advice I wish I’d known earlier.

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. The thing that’s wrong about imposter syndrome is that for the most part no one is thinking about you at all.

They’re too busy with their own doubts and their own work.

3. ​Find canvases for other people to paint on​.

Come up with ideas to hand over to your boss. Find what nobody else wants to do and do it. Find inefficiency, waste, redundancies.

The person who clears the path controls its direction, just as the canvas shapes the painting.

4. Very rarely have I ever let anyone go because they did not have the skills to do their job. It’s almost always their unwillingness to learn those skills or their inability to take feedback.

5. The boss/mentor/biz can’t want you to succeed more than you want it.

You have to be the driver of your own life/career/advancement.

6. When you’re lacking motivation, remind yourself: discipline now, freedom later.

The labor will pass, and the rewards will last.

7. Lengthen your timeline.

Opening my bookstore, ​The Painted Porch​ (delayed a year by COVID) taught me that ​it always takes longer than you think it’s going to take​. That’s Hofstadter’s law. And even when you take the law into account, you’re still surprised.

8. All success is a lagging indicator​... all the good stuff (and bad stuff) is downstream from choices made long before.

9. Lyndon Johnson said that the way to get things done was to get close to those who are at the center of things.

10. @RobertGreene's metaphor for mastery is being on the inside of something.

When we start a new job, we’re on the outside. As we put in the work, familiarize ourselves with every component, develop our intuitive field, we make our way inside.

11. Focus on effort, not outcomes.

​Just try to make contact with the ball​. Give your best effort, make contact with the ball. Let the rest take care of itself.

12. I’ve learned the hard way that almost all my mistakes and regrets come from not listening to my wife from the beginning.

You have to learn who knows you better than you know yourself, and you have to be able to trust and defer to them.

13. The trope that a day job takes away from your art or your hustle is stupid.

I wrote 3.5 books while I was at American Apparel. I started my own marketing company while I was a writer. I have my ​bookstore​. A job for someone coming up is like a trust fund you’ve earned.

14. When you’re building a business, salaries/staff can feel expensive. But if you succeed, you’ll regret giving up equity so cheaply.

15. There's a story about an exchange between Jerry Seinfeld and a young comedian.

The comedian approaches Seinfeld and asks him for advice about marketing and exposure. Exposure? Marketing? Seinfeld asks. Just work on your act.

​Your work is the only thing that matters​.

16. Talking about what you’re going to do makes you a lot less likely to actually do it.

Keep your plans to yourself.

17. From Peter Thiel: ​“Competition is for losers.”​

When people compete, somebody loses. So go where you’re the only one. Do what only you can do. Run a race with yourself.

18. The idea of “F*ck Yes...or No” is far too simple and has caused me quite a lot of grief.

Dropping out of college, I was maybe 51/49 on it. Leaving my corporate job to become a writer, maybe 60/40. The certainty comes later.

The truly life-changing decisions are never simple.

19. If you can afford to, delegate it. If you can’t yet afford to, automate it. Time is the most precious resource.

20. If it makes you a worse person, it’s not success.

If starting a business tears your relationships apart, makes you bitter or frustrated with people—then it doesn’t matter how much money it makes or external praise it receives.

That's not success.

21. Be patient—evaluate later.

The thing about leveling up in your career is that you really only realize that it happened in retrospect.

Don’t kick yourself now because you think you’re stuck. You might be the opposite of stuck and just not know it.

22. Having now been in pro locker rooms and boardrooms and briefing rooms with special forces operators and the Senate dining room—all very different worlds—they’re all basically thinking about the same core mental skills:

Resilience. Creativity. Focus. Collaboration.

23. A friend of mine just left a very important job that a lot of people would kill for.

When he left I said, “If you can’t walk away, then you don’t have the job...the job has you.”

That's 23 pieces of career advice I wish I’d known earlier.

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