“One has to kill a few of one’s natural selves to let the rest grow — a very painful slaughter of innocents.” – Henry Sidwick.
You, the ambitious young person, how many of your natural selves have you identified yet? How many of them are suffocating? Are you prepared for the collateral damage that’s going to come along with letting the best version of you out?
Ryan, college student 1 year from graduating with honors
Ryan, the Hollywood executive and wunderkind
Ryan, director of marketing for American Apparel
All dead before 25. May they rest in pieces.
I am a perpetual drop out, quitting, abandoning or changing paths just as many others in my position would be getting comfortable. By Sidwick’s terms, I guess I am a serial killer. This “slaughter” made room for the exponential growth of Ryan Holiday, published author. But he better not get comfortable either. Because he too may have to be killed one day. And that will be a good thing.
Because the future belongs to those who have the guts to pull the trigger. Who can drop out and fend for themselves. If you’re reading this site, you might already be contemplating a decision like that. I want to show you why it might be the right call for you and how to do it.
The Big Myth
“It wasn’t quite a choice, it was a realization. I was 28 and I had a job as a market researcher. One day I told my psychiatrist that what I really wanted to do was quit my job and just write poetry. And the psychiatrist said, ‘Why not?’ And I said, ‘What would the American Psychoanalytic Association say?’ And he said, ‘There’s no party line.’” – Allen Ginsberg
Let’s get the big myth out of the way. There’s not much dropping involved in dropping out of school. When I did it, I remember walking to the registrar’s office — I was so nervous. My parents had disowned me, I needed to move to a new city, the girl whose job I stole hated me. Why was I doing it? I’d just helped sign my first multi-platinum rock act and I wasn’t about to go back to the dorms and tolerate reading in the newspaper about other people doing my work. I was 20 years old.
I’m here to drop out of school, I announced to the registrar (like I was some presidential candidate who thinks he literally has to throw his hat into a ring). In fact, as my advisor informed me, that wasn’t exactly necessary. I could take a leave of absence for up to a year and possibly more, without even jeopardizing my scholarship. I braced for the same condescending, paternalistic lecture I’d gotten from my parents. It didn’t come. These people were happy for me. And if I submitted the right forms, I might even be able to get course credit for the work. How’s that for a party line?
So I took the plunge, and like many big risks, it turned out that dropping out of school was more manageable than I could have ever anticipated.
What I Wish I’d Known
I get a lot of emails from kids who are on the verge of dropping out. They always seem so scared. And I empathize with them. I know I was scared when I quit. Even billionaires, years removed from the decision that has now, in their case, been clearly vindicated, still speak of the hesitation they felt when they left school. Were they doing the right thing? What would happen? Were they throwing everything away?
It’s the scariest and most important decision most young entrepreneurs, writers, artists will ever make. So naturally, they take it very seriously. But doing that — taking it so seriously — almost wrecked me.
I remember pulling into a parking space one day a few months after dropping out, stressed and on the verge of a breakdown. Why am I killing myself over this?, I thought. It’s just life. Suddenly, a wave of calm washed over me. I was doing what young people are supposed to do: take risks. There is no need to stress over anything so seriously, let alone school (as someone told me later, he’d gotten sick when he was in college and missed 18 months of school. He’s 50 now and a year and half seems like two seconds). I’m not going to starve. I’m not going to die. There is nothing that can’t be undone. Just relax. Relax. And I did. And it worked.
If I’d realized it sooner, I could have avoided many needlessly sleepless nights.
I also wish someone had given me some more practical advice:
- Try to have a few months money on hand. It makes you feel less pressure and gives you more power in negotiating situations.
- Keep a strong network of friends — college friends especially. The unusualness of your situation is a warping pressure.
- Keep connected to normal people so you can stay normal.
- Take notes! I wish I’d written down my observations and lessons for myself the first time I dropped because it wasn’t my last time and I could prepared better for round II and III.
Why I Did It Again (and again)
When I dropped out of school, I was betting on myself. It was a good bet (one that surprised me, honestly). In less than 3 years, I’d worked as a Hollywood executive, researched for and promoted multiple NYT bestsellers, and was Director of Marketing for one of the most provocative companies on the planet. I had achieved more than I ever could have dreamed of — the scared, overwhelmed me of 19 could have never conceived of having done all that. (Which is why I killed that younger version of me). Yet, I knew it was time to drop out again. The six-figure job had to go. It was time for the next phase in my life. What I had, just like college had been, was holding me back.
That’s exactly what I did. I left and moved 2,000 miles away to write a book. It was wracking and risky and hard for everyone in my life to understand. But I was prepared this time. I knew what to expect. I’d saved my money, I built up my support system and I refused to take it too seriously. Whatever happened, I probably wouldn’t die.
…and I didn’t. In fact, within six months I’d sold the book to Penguin for several times my previous salary and was securely on my new path.
Welcome to the Future
I, and the many people who email me, seem to have a funny habit: We repeatedly leave and give up the things that most people work so hard to achieve. Good schools. Scholarships. Traditional jobs. Money. We don’t believe in sunk costs. If that sounds like you, then you’re probably a perpetual drop out too. Embrace it. I have.
I know that I will do it again and again in my life. Why? Because every time I do, things get better. The trial by fire works. It’s the future. The institutions we have built to prop us up seem mostly to hold creative and forward thinking people back. College is great, but it is slow and routine. Corporations can do great things, but fulfilling individuals is not one of them. Money is important but it can also be an addiction. Accomplishments like a degree or a job are not an end, they are means to an end. I’m so glad I learned that.
On your own path in life, remember the wise words of Napoleon and “Trade space for time.” (Or if you prefer the lyrics of Spoon “You will never back up an inch ever/that’s why you will not survive.”) Space is recoverable. The status of a college degree, the income from a job — recoverable. Time is not. This time you have now is it. You will not get it back. If you are stuck in a dorm room or wedged into a cubicle and what you are doing outside of those places is actually the greatest possible use of you, then it’s time to drop out.
Acknowledge, as Marcus Aurelius writes, the power inside you and learn to worship it sincerely. It may seem counter-intuitive that dropping out — quitting — is part of that, but it is. It’s faith in yourself. It’s about not needing a piece of paper or other people’s validation to know you have what it takes and are worth betting on. This is your life, I hope you take control and get everything you can out of it.