/ Life

An Honest Year as a Dropout

Behind the smoke and mirrors of leaving school

It seems like leaving school is becoming more common, so I wanted to share a few honest thoughts for those considering it and for those who may be curious. Besides, there’s something self-indulgent, something intoxicating about sharing your own story.

This is what happens behind the music. This is what actually happens behind the press-approved, success-heralding stories of leaving school.


I left college last May.

“Left college” is what I say, because I cringe when hearing the word “dropout.” I cringe because it could have been the long nights in the library and endless pool of not-yet-friends. It could have been unpredictable dinner dates and study sessions turned late night talks. It could have been walking up that podium, diploma-in-hand, frightened by an uncertain life ahead.

But, we give that up. Let’s imagine living through it yourself.


It’s August, and you just finished your internship. You love SF.

Most don’t drop out intentionally. A project becomes a company, you chance upon a Fellowship here or there, the company you interned at explodes—all of a sudden you’re out of school and living in San Francisco.

You face the world supremely confident in your potential, eager to take on anything. At first, the costs of dropping out are easy to rationalize: you’re in the shower or walking alone and you think “man, good thing I don’t have homework!” or “I have so much freedom to do anything!” You experience some growth, grow more excited, and work harder every day.

You flaunt your proud new “dropout” tagline. You write some blog and garner attention, maybe even get some press. You think about the possibilities you could have with VC money. You dream big and you act like the next Zuck or Gates. Hell, you might even think you’re Jobs.

Of course, you’re not. You find out the real world isn’t as welcoming and insular as college, and people don’t give a shit about your ideas, your dreams of changing the world. You learn about “sales” and how MBAs are valuable, how important business strategy is. The company doesn’t hit the hockey stick growth and crashes, or you find that running a startup is a hell of a lot harder than you thought. Or you get lucky. Most don’t.

But you keep on going. You’re hellbent for success and returning to school is the last thing on your mind.


It’s now November and you’re growing tired of the balmy weather.

You begin to find living alone really, well, lonely. All the interns have left. Housing is expensive in the Valley, and the fear of failure is always looming over your head. You learn about bill payments, credit card fees and interest, and grasp why being a grownup is not easy. Jesus, imagine caring for kids.

When your fellow dropout friends start to do well, you begin to grow jealous instead of happy. It becomes a competition with no winners, each vying for the best story to tell. There’s a lot of jealousy, and you’re left confused wondering why you’re not doing as well when you work just as hard.

The costs of dropping out manifest over time. Calling a friend and hearing stories through the grapevine; a Snapchat here; a Facebook photo there. Your resolve in staying out of school lowers each time you spew bullshit like “We’re killing it man! Growth is crazy!” while they’re home during break. Yeah, Thanksgiving is tough. Really tough.

As you stop working out, your health declines and you put on a dropout 15. You begin to lose sleep. You stop seeing your friends, and you lose your “cool factor.” In the midst of all of this, you realize there’s a reason why depression is prevalent in the Valley as you sink in a spiral of I-don’t-knows.

You find out that age and experience matter a lot. What you used to expect to be easy, like hacking together projects or not worrying about competitors, doesn’t apply in the real world. Turns out, what you thought you were knowledgable in… you know nothing at all.

You develop a severe case of imposter syndrome.


It’s January, and your friends are on winter break. You despise this city.

You’ve hit rock bottom.

You’re 19 and you’re broke.

You work your ass off but nothing’s turning around.

You think you know nothing.

You drink and have put on some heft.

Your family thinks you’ve gone insane and disappeared.

Your old friends don’t even call anymore.

You start to believe it when people tell you that it won’t work.

You’re almost certain you made the wrong choice.

Worst of all, you’re a fucking loser.

But this is what you left college for, you left for the risk we shoulder as proof of being more daring than the rest. We left for the adventure, the stories, the guts and glory.

Did you think it would be easy?


March and spring come. You realize that the birds don’t sing here.

Desperate and out of money, you realize you need to get your life back in shape. You come up with crazy ideas, anything that doesn’t lead to you failing and going back to school. Maybe you should try what Zenefits did and buy a billboard. Or copy Airbnb and hack Craigslist. Maybe you should go try and raise some money with no metrics.

You’re still broke.

Through all the noise, you realize you just have to suck it up. You put your head down and do the hard work.

You realize that your poor health is causing your work to decline so you begin to work out again. You learned about “nootropics,” Paleo, and Soylent. You consider hopping on the bandwagon.

You begin regulating your sleep schedule, and find yourself to be two times more productive with two times less coffee.

You relax a bit more, after accepting that the fate of the company was not tied to your own health. You start taking more time for yourself over weekends to explore Dolores Park, Sutro Baths, and other namesake places you didn’t get a chance to go to yet despite living a mile away.

You stop going to conferences to “network” after realizing you have never met anyone you care about or learned anything useful while listening to some famous guy speak.

You become more selective with how you spend your time.

You stop responding to requests for coffee and spend more time with your real friends.

You call Mom and Dad more often, instead of dismissing them to the standard “I’m busy” response. You miss your sister more every day, and you break a tear when she tells you about Homecoming and things you can’t be there for.

You begin to be more open and honest with them.

You start doing real work. You stop complaining, start closing sales, acquiring users, and do anything you can that contributes to your business surviving and not its vanity metrics. You stop saying stupid things like “everything’s going great!” and be honest with other founders and friends.

You realize you can’t use the excuse “We just started 3 months ago” anymore and that nobody cares about your age.

You’re not the naive kid you once were.


April arrives and it rains everyday. You conclude you hate the rain.

This time, it’s real. You don’t have much time. College is coming to an end for your peers. Being competitive, you want to show them what you were capable of after all these months in dormancy.

Things finally start turning around. Sales and user metrics are starting to climb, increasingly so. Your social life has taken a hit the past few months, but you start to feel happier and free being solitary. Your heart and head don’t hurt as much, and your body fat is shooting down fast. You still feel like you’re financially screwed, but at least you know to pay bills on time.

Customers start raving about your product and its near-instant support because you do everything you can to make them happy and paying. You freak out over small bugs, and hope for the best as requests go up.

Acquaintances are starting to take notice, asking about job positions. You begin getting emails from VC’s claiming interest (alongside your bank accounts asking for their money). More coffee meetings come up and you keep pushing them back. You know your time is better spent working.

Things that you used to think were impossible are now within grasp. Programs you read about, like the elusive “Thiel Fellowship” and mythical “Y Combinator” are now not statistical outliers. Those 1% acceptance rates don’t phase you anymore and you apply anyway, knowing that whether you get it or not has no indication on how you do.

You get both…

But you are surprised by how worried you still feel. A year ago, you wanted these things so, so much. So much, that you dreamed about it. You were inspired by the incredible things these founders and fellows did.

And now, you’re one of them. But rather than grant yourself any satisfaction or downtime, you are more scared of going back to the hell you were in a few months ago than ever before. You move even faster. You are wary of sidetracking your focus and aren’t sure of what to be excited about anymore.

Some would say you have matured. You know you’re just really paranoid.

Your team finally begins to take VC meetings and realizes the careful dance of raising money while young. You’ve heard all these horror stories and try your best to do it the right way. You screw some things up, but you wind up closing some money from a genuine, supportive group of people you trust. You remain insecure and worried.

You start to own your sales calls and you’re no longer afraid to play with seasoned vets on the same playing field now. This is business. You become less afraid to lose it all. Because, ironically you begin to think that school isn’t so bad an option anymore. By now, college seems like a faraway dream that you might one day return to. Might.

You see hints that your work is paying off.


It’s August. Most don’t make it this far. You kind of like the fog again.

And so, now you’re here.

You’ve been in the Valley for a year.

You’ve learned a lot. You’re a YC Founder, a Thiel Fellow, and you’re VC-backed. You’re really sharp, really fit, really diligent, and you aren’t broke anymore. You parry with the old guys during meetings, and you don’t take no for an answer. You’re ruthless. Your family and friends are rooting for you. You’ve been through shit, and now people think you’re the shit.

But you know that things will crash again. You’re weathered and tired and beaten and sore, but at least life isn’t so bad. This time, you’re ready.

You feel old and out of place at college parties. You’re no longer jealous or worried about your friends at school, because you just value different things now. Not better things, not worse, just different. Your friends and family are more understanding and supportive after seeing you go through a tumultuous year.


Most people think dropouts are crazy.

Most people think we’re crazy brave or crazy smart, all-in-all super crazy. Maybe you think we have lots of money and lead insane lives. Maybe you think we’re idiots for working away our young years. Myths are a soup of misconceptions with a pinch of truth and a sprinkle of exaggeration.

It’s true, you may have nothing to do with startups or alternative education. And I will never go near your homework and would fail your classes.

But we are far more similar than we are different. You and I are both young and human. We’re both on Tinder looking for each other to Netflix and chill. We work out (to eat more food). Maybe you take photos too. Do you also like beach days? We both have a love-hate relationship with Buzzfeed.

But in recent times, it seems like Silicon Valley and top schools have become affixed to the romantic conception of dropping out, hearkening to a mythical Silver Age of Golden Gates and Zeus Zuck.

If it wasn’t clear: there is no glory in leaving school. There are only guts.

Let me repeat that. There is nothing glamorous about our lives, nothing remotely close to “sexy” about leaving school. So don’t drop out if you’re pursuing that lifestyle. If you’re crazy and want your ego crushed for good, maybe you should consider it. Most people belong in school. But either way, we can still get along just fine. Your life is difficult, and so is mine.

You should go back to preparing for school, right? Don’t slouch too much or you might end up like me. I wonder what your parents would think of that.

Welcome back to school.

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