A Hard Right Turn

June 16, 2011

At 20, I moved to Los Angeles to live with Tucker Max for the summer. I didn’t know it then, but I was dropping out of school and I would never come back. At 24, I’m dropping out again. Last week I packed up what little I still own and moved to New Orleans.

When I did it the first time, I was scared. Scared all the time. It’s funny because this time, I was worried every day I had my job for the last year. Is this who I am going to become? What am I supposed to do with all this? But when I left, actually the second I made the announcement I was leaving, all the fear left. As soon as I was given control of my life back, I felt calm and comfortable. At peace. It was a nice bookend to realize this, to realize that fear I felt both times was rooted in a single theme: taking control of my life. Leaving school, that was taking it. Leaving a career, that was acknowledging that I’d given too much of it back.

But this was always my plan. When I made it, I thought it’d take two years; it took closer to three. In the middle of those two events, I’ve racked up more than I ever would have expected. I was the Director of Marketing at American Apparel. I researched for a bestselling book by Robert Greene and 50 Cent. I’ve advised on the release of five of them now. I’ve bought millions of dollars in advertising. I’ve seen my work written about in every major publication I can think of. I’ve been offered two book opportunities and turned them down. I ran one of the biggest and earlier Groupon deals. I’ve traveled. Met with important people. Been humiliated and learned from mistakes. Had power, used power, observed powered. And at the end of it, all I could think was: so…

The middle had its ups, no question. I’m beyond grateful to the people who allowed me to take a shot at them. But it was grueling. Shakespeare once wrote that “between the acting of a dreadful thing and the first motion, all the interim is like a phantasma or a hideous dream.” It was something I struggled to appreciate for a long time, trying not to lose control of the wheel and veer off in a direction I didn’t want to go. To trust in the plan, to accept the commitment. Some people are meant for a certain kind of life. Some are not. It’s important to know where you fall in that.

I’ve not talked about these things on this site for a few reasons. Mostly because I was busy actually doing them. The other reason was I didn’t want to be like the rest of the charlatans out there. I wanted to build up something solid before I talked about myself and my opinions. I just couldn’t see what I’d get out of doing it before that, except feeling like a douche. But now you have it, there I am and ‘what I do.

What’s next for me is a book. I’ve already begun working on it. Some of the ideas of already been floating around on here in posts (see: this and this) but it is mostly new material and not what you’d expect of me. This is not the book I’ve dreamed of writing but is the book I HAVE to write now. If I do it right, it will open the door for the former as well.

Anyway, here I am at 24. Not close to the millionaire I naively promised myself years ago I’d be by the time I was 25. But I do have more than I know what to do with. And thanks to Philosophy I can’t see myself realistically chasing that goal very hard anymore. Because when you figure out what is important to you in life, you can throw out all the rest. You can stop chasing ghost and shadows and illusions. You can lean on what is real and what is necessary. And you can laugh and pity those can’t. You can realize, as Seneca wrote, that too often they ‘win’ at the cost of life.

And so you focus on yourself and what you need to do. And block out all the rest.

Ryan Holiday

I'm a strategist for bestselling authors and billion dollar brands like American Apparel, Tucker Max and Robert Greene. My work has been used as case studies by Twitter, YouTube and Google and has been written about in AdAge, the New York Times, Gawker and Fast Company.

46 responses to A Hard Right Turn

  1. Word.

    (Voice in my head says, “You need to say more than ‘Word,’ jackass,” but I was going for a digital/text-based equivalent to one of those face-to-face nods where both parties have no doubts about what they’re doing.)

  2. Congrats on the move and all you’ve accomplished over the years. Looking forward to the book.

  3. Glad you started on the book. Looking forward to it. Why New Orleans?

  4. Nice. It takes a lot to pack up everything and move to another place, but it is always worth it. Glad to see you’re doing it all again.

    I’m looking forward to hearing more about the book and on life in New Orleans.

  5. I, too, have been in this situation. It is a waking from a dream.

    This post reminds me of an earlier one you had written, that impacted me: “the price of a suit.”

    Currently, corporations are in desperate need of people who are creative and intelligent and — let’s face it — daring. They even admit to it. But the challenge is, people with those qualities don’t always “fit” inside that peculiar construct that is The Corporation. It is a narrow space that one must wedge into — emotionally, creatively, even physically (if anyone has ever spent years working inside a building where the windows did not open and all air was piped-in, then they probably understand was I am saying both metaphorically and literally)….

    { twitter = @danenow }

  6. Hey Ryan, that’s really cool that you lived with Tucker Max. I don’t know much about him, but I know my sister has his book “I Hope They Serve Beer in Hell.” It sounds as thought he is a kind of “pick-up artist,” or no?

    You’re other experiences sound really impressive too, doing marketing for that book with Robert Greene and 50 Cent (I assume – the “50th Law of Power?”)

    Don’t be hesitant to talk more about these associations. I’m sure many of your readers would love to learn more about your experiences.

  7. Oh and – duh! – good luck on your book.

  8. I’m really excited for the book. The abandoned shells post is one of your better ones, and the W.S. Trow/Boorstein recommendations are my favorite things you’ve shared here outside of Seneca/Aurelius. Best of luck to you.

  9. Ryan’s writing is a treasure because he doesn’t need to search for novel, cute, fragmented subjects to cover. He discusses central, timeless issues without being cliche. Also, given his background in marketing, he has the confidence to deliver authentic analysis, because he knows he can sell without pandering to a wider demographic. Whatever form the book takes, I hope it is heavy on self-help, because Ryan is one of the few individuals whose prescriptions are worth filling.

    • Word.
      One reason this blog makes me feel alive: even those who comment often express a similar intelligence and elegance. I envy the quality of the community.

  10. Awesome post, Ryan. So glad to see you’re doing what you want to do. I’ll let you know when I’m next in New Orleans!

  11. Congrats and good luck. Fwiw I’d pre-order your book in a second.

  12. You seem to have no sense of the absurd. It’s just success is great and anything standing in its way isn’t worth bothering with. Kind of boring.

  13. Congratulations. Can’t wait for the book.

  14. Its been such a journey following this blog. Thank you so for contributing and I look forward to your book!

  15. Aw, N’awlins.

    Nice selection. Water, blood, and dirt mix there. Everything mixes there. It is one of few places in the United States that maintain its own culture. Pure that place is and fitting as many people often speak about it being so dirty.

    Stories in that city. Stay there long enough not to become one. That line, I found, is hard to walk.

    Rumor has it that I am to be there for a while myself. Maybe we will cross streets.

    –Enjoying the reading list, btw.

    • I’m trying to stay holed up in libraries and dark rooms so I can get this thing finished but you can always email me if you are down here. I’m in the Garden District.

  16. Heavy! Blokes bagging you about being humourless! Your stuff’s fucking awesome. Profound content on the web’s pretty hard to find, can’t wait to read more of your philosophies and get your book.

  17. Ryan, thanks for a very insightful post. You are the most refreshing blogger I have come across in my quest to connect with some unique, unconventional thinkers online. I am intrigued by your love of philosophy and your very obvious determination to regain control of life by “dropping out”, trimming down and focusing on the very core of what is meaningful to you. Do you think that this core that you can “lean on” , the “real” and the “necessary” is found within you or in something else… a transcendent element of some kind. I don’t necessarily have a fixed answer and I resist the pat replies to this kind of questioning.
    Again, I’m impressed with your focus..

    • Say that again? Is what I lean on in me or in other things? If that’s the question, I think it’s both. It’s reducing things to their essence–that which is real. And within yourself, focusing on what you can control (say, your attitude about events rather than the events themselves) and worrying only about that.

      • Thanks, that was the question.

        How successful do you feel you have been at “reducing things to their essence”… I have definitely struggled with that – first because “essence” seems to be a matter of perspective (the “essence” of something is always subject to having more layers pealed off and my confidence RE the truth has humbled me because I have been wrong more than I have been right) and second because even the limited view of the “essence” of things that I think I do see clearly is a tough reality on which to act courageously.

  18. If you ever want to find out about the rest of Louisiana (i.e. the not as cool but still cool northern part), let me know! I can definitely show you around the greatest areas of the north Louisiana.

  19. I come back to this post every time I struggle with where I am, where I’m going and get wrapped up looking at others who are more successful.


  20. Ryan, this is insanely encouraging. I love how your writing really tells people to follow their heart without explicitly shoving it down own throats 🙂 Your journey (as much of it as I’ve read so far) sounds way more interesting than the conservative corporate drudgery that most people concede to. Thanks for keeping it real at the end too.

    As successful as you’ve been, you don’t try to sell this story like a rags to riches fairytale and I think that keeps your writing a lot more grounded an applicable for people to learn from. Looking forward to getting to know your writing a bit more.

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