No Matter What You Want To Change, It Won’t Be As Terrifying As The First Step You Take Toward Making It

I almost immediately regretted dropping out of college. My boss in Hollywood, who’d urged me to make the leap, gave me a week to get my stuff together, get an apartment and report for my new job. The day I showed up, I got some alarming news: He’d suffered a medical emergency and checked into a clinic for 30 days. The girl who I was replacing hadn’t been informed. Oh, and the agency’s other partner decided he didn’t like me and called me into my office to renegotiate my job. I walked out making 25% less than I’d just left school for–and there was no one I could call.

It was like Arrested Development: I’ve made a huge mistake.

You’d think this would have soured me on dropping out and taking risks. But it’s basically had the opposite effect. It doesn’t matter what I do, it’s not going to be as terrifying as that. I walked out of that room getting screwed out of some salary but I was also a little bit less of a kid too. It’s a trade off.

When I stepped away from American Apparel full time in 2011, I was making another big bet. I wanted to write a book. But I was worried that if I sold it via the traditional channels (most non-fiction authors sell a book proposal and then get written), it would get the edges shaved off or get turned into something I didn’t want. So I funded the project myself. To afford it, we moved to New Orleans…where I stupidly selected a 300 square foot studio in this 200-year-old dilapidated mansion where my girlfriend, dog and I could live while I wrote. I swear to god, this–and the heat–almost killed me, and us.

But hey, it wasn’t as bad as the first time. And it paid off too. It’s always going to be painful to eliminate old versions of yourself and the comforts you’ve gotten used to.

When I talk about dropping out, about taking these big risks, I don’t do so slightly. I know what they really entail. I’m not some rags to riches story–I’ve had plenty of privileges–but I know what it feels like to go all in. I know how scary that is. It’s why I like the imagery in those quotes about killing off parts of yourself, because it’s gruesome, it isn’t clean and most people flinch.

It’s still a good idea though. The math still works. For three reasons, in my opinion.

Education costs have plummeted.

I like to say that my education began the day I left school. Not just because it’s cute, but because it’s true. I’ve lived that Recession Proof Graduate story. It was easy for me to become a different kind of student, to shed the skin of a college kid and become an apprentice because of the convergence of a whole bunch of factors. Not only was I training directly under a Hollywood producer and working as a research assistant for Robert Greene, but every day I was reading blogs and articles from some of the smartest, most forward thinking people alive. I would read Mark Cuban and Tyler Cowen. Think about that: a billionaire kicking off thoughts in his spare time and an economist at a school whose classes I never could have gotten in, were both available to me, a random kid. I remember one day, I was having trouble with some bullshit at work and I emailed a question to Chris Anderson, who was then the editor in chief of Wired. He responded like ten minutes later. Oh and when I wasn’t working, I was taking Yale classes for free online.

All of the things that I learned in this period, this crash course I was on, it wouldn’t have been possible in any other era. Not as quickly or as cheaply anyway. I went directly to the seat of knowledge, and I learned enough to create a real career out of it. And this was roughly seven years ago–if anything it’s more possible now to learn what you need to learn to become something different.

Marketing/startup costs have fallen too.

Do you know what the combined marketing budgets on my three books have been? The answer is I don’t know…because they didn’t really have one. My total investment in my blog and my email list has been basically nothing as well. What I mean to say is that once you have an idea–once you have the thing you intend to do–the way to make your name and build your audience is with hard work and time. That’s all it takes.

I talk about this a lot in Growth Hacker Marketing. What we’re looking at today is a host of startups who have launched with essentially zero traditional marketing. They didn’t hire publicists, they didn’t spend a bunch of money on advertising. They start with a “Minimum Viable Product,” test it on the market and pursue only the versions that work. The marketing is built into the idea, it spreads itself, it acquires customers because it is good.

Startup costs–making an idea into a reality–have plummeted too. Airbnb launched with a $20,000 seed round from Y Combinator. Before that, they funded themselves by selling boxes of Obama-O’s cereal during the 2008 Democratic Convention. But that was enough–enough to build the site, validate the idea and hold them over until the real investors finally came on board. Today that company is worth $10 billion, probably more.

My point is going from employed to self-employed, which was my next transition, is easier than it ever has been. If you want to murder the guy in you who has to wear a suit to work, that’s possible. That’s the easy part.

We’re all just making it up as we go along.

One of my clients, James Altucher, wrote a book last year called Choose Yourself. He’s a guy who has made and lost a couple fortunes on Wall Street and in the Silicon Valley. He’s on the board of a staffing company for Fortune 500 companies and what he saw there is this: the old system is falling apart and it is not coming back. These companies are shedding jobs they don’t plan to replace. We’re going to have to make our own way going forward. You have to choose yourself.

I agree with that. Do you know who John Lee Dumas is? Most people probably don’t. But this guy, an officer in the US Army for eight years, started a podcast about two years ago. This is podcasts–that old tired medium that I remember having a flash of popularity in the mid 2000s and then dying off. Well, his show made $2M dollars last year and has been downloaded nearly 10M times. He learned how to create a popular show and then created a course to teach people how to do the same thing. Now he makes a lot more money than I do. The dude works out of his house and does a show with an interesting person every single day.

How’d he get so lucky? It’s not luck, he made up a ridiculous gig for himself. Who would have thought you could make money teaching people this stuff? It’s the same story with all these experts–they got really good at something and then thought, yeah, I’m going to make a go at this.

When I left school I had no idea it would lead to where I am right now. I never thought I would have a marketing company. Or that people would pay me to consult. Or that I’d have written three books this quick. No clue on any of that. I was just making it up as I went along, taking advantage of individual opportunities. That’s how it goes–for all of us.

_____

“One has to kill a few of one’s natural selves to let the rest grow — a very painful slaughter of innocents.” – Henry Sidgwick

I’m not sure I remember who I thought I would be when I was first starting out but it was something very different. Like all people, I had the potential to be many things. My skills, my desires, they could have been combined anyway.

But it is by this process of elimination, of taking risks, of dropping out, that you forge who you are. It’s always been this way.

It isn’t for everyone, I understand. Some people are afraid. Some people want a cleaner, clearer path. By all means, take it.

But for some of us, that doesn’t work. We have to undergo this gauntlet to find out who we are. We’re willing to endure the uncertainty–and the terror–to get there.

The good news is that certain trends have made this easier than ever before, and they are like a wind at your back. The other part is never going to change: as kids, we can be many things, but to become who we are, takes something more.

Where I am going next I don’t know, but it’s going to involve that same process. And I’m excited for it.

The thoughts in this piece were originally prepared for a talk I gave for US Military Veterans at Fort Bragg as part of American Dream U.