On Our Final "Virtual Route 66" For Feburary 2024: On Career Advise ((Courtesy Ryan Holiday))

 

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

From my first desk job working at my college newspaper.

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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, about some little success I’d had on some project. He was very busy and frustrated that I’d interrupted, but politely, he said, “Ryan, you are calling me to tell me that you did your job.” I thought of that conversation when I saw that famous scene in Mad Men where Peggy complains that Don never says thank you. “That’s what the money is for!” he tells her.
3. 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.
4. When I was starting out as an assistant in Hollywood, someone told me that the best thing I could do was make my boss look good. Don’t worry about credit, they said. Forget credit so hard that you’re glad when other people get it instead of you. It ended up being pretty decent advice, but it was nowhere near the right wording. I think a better way to express it would be: 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. 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. When I was 20 years old, I was working at this talent agency in Hollywood, and I got invited to this important meeting. As they were talking about stuff, I interjected and said something. My mentor took me aside after and he said, why did you say that? Did you think it actually needed to be said or did you just feel like you wanted to have something to say? I think about that all the time. It’s in The 48 Laws of Power — 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. 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.
8. I was working full time at American Apparel but planning my next move, saving my money and thinking about writing a book. Over lunch one day, Robert Greene told me, Ryan, while people wait for the right moment, there are two types of time: Dead time—where they are passive and biding and Alive time—where they are learning and acting and getting the most out of every second. Which will this be for you?
9. When you’re lacking motivation, remind yourself: discipline now, freedom later. The labor will pass, and the rewards will last.
10. When I first moved to Austin in 2013, I went out to lunch—fittingly—with a writer named Austin Kleon. I was a longtime fan of his book Steal Like an Artist (his book Keep Going is another favorite). After we ate, he drove me around the city, showing me things and giving me advice. Austin was a little older than me and already married with kids. I remember asking him how he made time for it all. “I don’t,” he told me. “Life is about tradeoffs.” And then he gave me a little rule that has stuck with me always: 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.
11. 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.
12. ​All success is a lagging indicator… all the good stuff (and bad stuff) is downstream from choices made long before.
13. Lyndon Johnson said that the way to get things done was to get close to those who are at the center of things.
14. Robert Greene’s metaphor for mastery is being on the inside of something. 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. This is a metaphor from Robert I think about constantly. I don’t want to be an outsider on anything I do, I want to make my way inside it.
15. 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.
16. In 2013, I started a business with a partner that my wife warned me against working with. I remember explaining to her why she was wrong and that I couldn’t possibly not do this because of some vague gut instinct of hers. The business turned into a nightmare, and it turned out that this partner was not someone I should have worked with. This shares a commonality with almost all my mistakes and regrets: Not listening to my wife from the beginning. 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.
17. The trope that a day job takes away from your art or your hustle is stupid. There was a great exhibition at the Blanton Museum a couple years ago about artists who had day jobs. I wrote 3.5 books while I was the Director of Marketing 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. It helps.
18. Learning is priceless. Robert Greene used to have to nag me to submit my hours when I worked for him. To me, the money was an afterthought, I knew the real return was my access to him, that he would answer my questions, that I could see how a real pro did the job.
19. My career in Hollywood came to an end when one of the talent managers took a dislike to me (I told this story at the beginning of my appearance on Joe Rogan). When I ended up at American Apparel, I asked Robert Greene about how to prevent that from happening. He pointed out my problem before was that I had only had one ally or patron. I needed to cultivate relationships with multiple decision makers/power brokers at the new company, especially a place as political and full of intrigue as American Apparel. So that’s what I did–you don’t want to be dependent on a single thread or a single vote of confidence. You need redundancies. You need relationships.
20. When you’re building a business, salaries/staff can feel expensive. But if you succeed, you’ll regret giving up equity so cheaply.
21. Dov Charney said another thing to me that I think about a lot. I was pointing out that some store (which had just opened) wasn’t doing well. He said, “Run rates always start at zero.” The point there was: Don’t be discouraged at the outset. It takes time to build up from nothing.
22. There is a story about an exchange between Jerry Seinfeld and a young comedian. The comedian approaches Seinfeld in a club one night and asks him for advice about marketing and getting exposure. Exposure? Marketing? Seinfeld asks. Just work on your act. Your work is the only thing that matters.
23. Talking about what you’re going to do makes you a lot less likely to actually do it. Keep your plans to yourself.
24. The distinction between amateur and professional is an essential piece of advice I have gotten, first from Steven Pressfield’s writings and then by getting to know him over the years. There are professional habits and amateur ones. Which are you practicing? Is this a pro or an amateur move? Ask yourself that. Constantly.
25. Peter Thiel: “Competition is for losers.” I loved this the second I heard it. When people compete, somebody loses. So go where you’re the only one. Do what only you can do. Run a race with yourself.
26. The idea of “Fuck 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. Right now I’m about to do something big that I am both excited and terrified about. The point is: The certainty comes later. The truly life-changing decisions are never simple. If I had only ever done things I was absolutely certain about, I’d have missed out on experiences I love. Conversely, I regret a good chunk of my “Fuck yes’s” because I was caught up in a fit of passion or bias. The whole point of risk is that you don’t know.
27. There is a story about the manager of Iron Maiden, one of the greatest metal bands of all time. At a dinner honoring the band, a young agent comes up to him and says how much he admires his skillful work in the music business. The manager looks at him and says, “HA! You think I am in the music business? No. I’m in the Iron fucking Maiden business.” The idea being that you want to be in the business of YOU. Not of your respective industry. Not of the critics. Not of the fads and trends and what everyone else is doing.
28. If you can afford to, delegate it. If you can’t yet afford to, automate it. Time is the most precious resource.
29. The best coaches and CEOs aren’t the ones who succeed just on the field or in the boardroom. The true greats are measured by their coaching tree—what the people who worked for them, who they mentored, who they inspired go on to do.
30. The thing I’ve learned about leveling up in your career, or breaking through different ceilings, is that you really only realize that it happened in retrospect. Just like you don’t notice your hair growing or your face aging, you can’t really feel it as it’s happening. Be patient—evaluate later. Don’t kick yourself now because you think you’re stuck. You might be the opposite of stuck and just not know it.
31. 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.
32. 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—I have come to believe that elite performance is elite performance is elite performance. While these folks all do very different jobs at very different levels of fame or fortune, they’re all basically thinking about the same handful of things, accessing the same core mental skills: Resilience. Creativity. Focus. Collaboration.
33. The best decision I ever made was taking a pay cut to write The Obstacle is The Way (less than half what I got for my first book). I knew it was what I wanted to write. I thought it could sell. I had my day job. It still seemed like a TON of money to me. Sometimes you have to take a step back to go forward.
34. But if I am content with what I have, won’t I stop getting better? No. We play better with house money. Feel better too.
35. If you never hear no from clients, if the other side in a negotiation has never balked to something you’ve asked for, then you are not pricing yourself high enough, you are not being aggressive enough.
36. 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.
37. 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.”