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

Ryan Holiday

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  • 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.
  • It’s in [[The 48 Laws of Power|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.
  • 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.
  • 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?
  • When you’re lacking motivation, remind yourself: discipline now, freedom later. The labor will pass, and the rewards will last.
  • 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.
  • All success is a lagging indicator… all the good stuff (and bad stuff) is downstream from choices made long before.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • Talking about what you’re going to do makes you a lot less likely to actually do it. Keep your plans to yourself.
  • 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.
  • you can afford to, delegate it. If you can’t yet afford to, automate it. Time is the most precious resource.
  • 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.
  • 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
  • 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.”