You only have to be right once

The hard thing about planning your life is you have no idea where you're going, but you want to get there as soon as possible. 

Being up here in robes and speaking to all of you today wasn't exactly part of my plan seven years ago. In fact, I've never really had a grand plan — and what I realize now is that it's probably impossible to have one after graduation, if ever.

What got you here was basically being smart and working hard. But nobody tells you that after today, the recipe for success changes. So what I want to do is give you a little cheat sheet, the one I would have loved to have had on my graduation day.

If you were to look at my cheat sheet, there wouldn't be a lot on it. There would be a tennis ball, a circle, and the number 30,000. 

Clearly, the most important order of business was to Photoshop a logo and print out some business cards that said "Founder" on them. The next order of business was to hand them out at conferences, and tell girls "why yes, I do have a company." It was awesome.

But the best part was learning all kinds of new things. I lived in my fraternity house every summer, and up on the fifth floor there's a ladder that goes up to the roof. I had this green nylon folding chair that I'd drag up there along with armfuls of business books I bought off Amazon and I'd spend every weekend reading about marketing, sales, management and all these other things I knew nothing about. I wasn't planning to get my MBA on the roof of Phi Delta Theta, but that's what happened.

A couple years later, things started going downhill. I felt like I had to paddle harder and harder to make progress, and at some point I just snapped and couldn't deal with any more math questions about parallel lines or the train leaving Memphis at 3:45. I figured something was wrong with me. I felt guilty for being so unproductive. Starting a company had been my dream, and, well, maybe I didn't have what it takes after all.

So I took a little break. Of course, if you're in course 6, sometimes "taking a break" means writing a poker bot. For those of you who don't know what a poker bot is, what happens when you play poker online is first, you sit for hours and click buttons, and then you lose all your money. A poker bot means you can have your computer lose all your money for you.

But it was a fascinating challenge. I was possessed. I would think about it in the shower. I would think about it in the middle of the night. It was like a switch went on — suddenly I was a machine.

I was going to say work on what you love, but that's not really it. It's so easy to convince yourself that you love what you're doing — who wants to admit that they don't? When I think about it, the happiest and most successful people I know don't just love what they do, they're obsessed with solving an important problem, something that matters to them. They remind me of a dog chasing a tennis ball

The problem is a lot of people don’t find their tennis ball right away.  What scares me is that both the poker bot and Dropbox started out as distractions. That little voice in my head was telling me where to go, and the whole time I was telling it to shut up so I could get back to work. Sometimes that little voice knows best.

It took me a while to get it, but the hardest-working people work hard because working on an exciting problem is fun. So after today, it's not about pushing yourself; it's about finding your tennis ball, the thing that pulls you. It might take a while, but until you find it, keep listening for that little voice.

They say that you're the average of the 5 people you spend the most time with. Think about that for a minute: who would be in your circle of 5? I have some good news: MIT is one of the best places in the world to start building that circle. If I hadn't come here, I wouldn't have met Adam, I wouldn't have met my amazing cofounder, Arash, and there would be no Dropbox.

One thing I've learned is surrounding yourself with inspiring people is now just as important as being talented or working hard. Your circle pushes you to be better, just as Adam pushed me.

And now your circle will grow to include your coworkers and everyone around you. Where you live matters: there’s only one MIT. And there's only one Hollywood and only one Silicon Valley. This isn't a coincidence: for whatever you're doing, there's usually only one place where the top people go. You should go there. Don’t settle for anywhere else. Meeting my heroes and learning from them gave me a huge advantage. Your heroes are part of your circle too — follow them. If the real action is happening somewhere else, move.

The last trap you might fall into after school is "getting ready." Don't get me wrong: learning is your top priority, but now the fastest way to learn is by doing. If you have a dream, you can spend a lifetime studying and planning and getting ready for it. What you should be doing is getting started.

Bill Gates's first company made software for traffic lights. Steve Jobs's first company made plastic whistles that let you make free phone calls. Both failed, but it's hard to imagine they were too upset about it. That's my favorite thing that changes today. You no longer carry around a number indicating the sum of all your mistakes. From now on, failure doesn't matter: you only have to be right once.

I used to worry about all kinds of things, but I can remember the moment when I calmed down. I had just moved to San Francisco, and one night I couldn't sleep so I was on my laptop. I read something online that said "There are 30,000 days in your life." At first I didn't think much of it, but on a whim I tabbed over to the calculator. I type in 24 times 365 and — oh my God, I'm almost 9,000 days down. What the hell have I been doing? (By the way: you guys are 8,000 days down.)

So that’s how 30,000 ended up on the cheat sheet. That night, I realized there are no warmups, no practice rounds, no reset buttons. Every day we're writing a few more words of a story. And when you die, it's not like "here lies Drew, he came in 174th place." So from then on, I stopped trying to make my life perfect, and instead tried to make it interesting. I wanted my story to be an adventure — and that's made all the difference.