Ryan Holiday working on his colleges’ newspaper

24 Pieces of Career Advice I Wish I’d Known Earlier by Ryan Holiday

24 Pieces of Career Advice by Ryan Holiday

Parker Klein ✌️
Published in
4 min readMar 13, 2024

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1. Be quiet, work hard, and stay healthy.

It’s not ambition or skill that is going to set you apart but sanity.

2. Nobody is thinking about you

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. Don’t worry about credit

Forget credit so hard that you’re glad when other people get it instead of you.

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

Come up with ideas to hand over to your boss. Find people, thinkers, up and comers to introduce them to. Cross wires to create new sparks. Find what nobody else wants to do and do it. Find inefficiency and waste and redundancies. Identify leaks and patches to free up resources for new areas. Produce more than everyone else and give your ideas away. The person who clears the path ultimately controls its direction, just as the canvas shapes the painting.

5. Embrace learning

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.

6. Always say less than necessary.

Saying less than necessary, not interjecting at every chance we get — this is actually the mark not just of a self-disciplined person, but also a very smart and wise person.

7. You have to be the driver of your own life/career/advancement.The boss/mentor/biz can’t want you to succeed more than you want it.

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

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

The labor will pass, and the rewards will last.

9. Work, family, scene. Pick two​.

Your creative output, your personal relationships, and your social life — balancing all three is impossible. You can excel in two if you say no to one. If you can’t, you’ll have none.

10. ​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.

11. All success is a lagging indicator

All the good stuff (and bad stuff) is downstream from choices made long before.

12. Find your way into the inside

When we start a new sport, when we get our first job, when we approach a field we haven’t yet studied, we are on the outside of. But as we put in the work, as we familiarize ourselves with every component, as we develop our intuitive field, we eventually make our way to the inside.

“The way to get things done was to get close to those who are at the center of things.” — Lyndon Johnson

13. 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.

14. You have to learn whose judgment to trust.

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

15. You need relationships.

You don’t want to be dependent on a single thread or a single vote of confidence. You need redundancies.

16. Be cheap with equity

When you’re building a business, salaries/staff can feel expensive.

But if you succeed, you’ll regret giving up equity so cheaply.

17. Great things take time

“Run rates always start at zero.” — Dov Charney

Don’t be discouraged at the outset. It takes time to build up from nothing.

18. Your work is the only thing that matters​.

A comedian approached Jerry Seinfeld in a club one night and asked him for advice about marketing and getting exposure.

“Exposure? Marketing? Just work on your act.” — Jerry Seinfeld

19. Keep your plans to yourself

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

20. The difference between amateur and professional

There are professional habits and amateur ones. Which are you practicing? Is this a pro or an amateur move? Ask yourself that. Constantly.

21. Run a race with yourself.

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

​“Competition is for losers.” — Peter Thiel

22. Time is the most precious resource.

If you can afford to, delegate it. If you can’t yet afford to, automate it.

23. Be able to adapt and make use of new tools.

I have no idea what the long term implications of artificial technology will be, all I know is that the best approach as an individual is to find a way to use it to get better at what you do.

24. If it makes you a worse person (parent, neighbor, writer, whatever), it’s not success.

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

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Parker Klein ✌️

Former @Google @Qualcomm @PizzaNova. Building Twos: write, remember & share *things* (www.TwosApp.com?code=baller)