Apr 1, 2013 · 5 minutes

You just sold your company for hundreds of millions of dollars, and months later, you are still getting congratulatory emails from people you barely remember. You worked your ass off to build that company, and you genuinely deserve credit for what you achieved — sure, there was some luck involved. More than you even want to think about. Still, nobody can doubt the accuracy of your original vision, the outstanding decisions you made along the way, and your innate ability to execute. That’s why investors are flocking to your next deal. That’s why everybody wants to get your opinion on their new pitch. That’s why your college’s Alumni Council won’t stop hounding you.

But you’re not as good as you think you are.

You made a lot of mistakes along the way, and several of them almost capsized the ship before it could reach shore. Your dumbest decisions — and there were plenty — should have killed the company. You also took on too much capital, developed products that you knew were long shots, and you started monetizing a year later than you could have. If you do it all over again, you’ve got a plenty high chance of failure. Even you wonder whether you’ve got the “hustle” left in your fat body after so many years of sacrificing and grinding. There’s less to be scared of this time, and that alone should terrify you.

You just got an MBA from Harvard. This shit always came naturally to you, and you stood out even amongst the "best of the best." Baker Scholar, bitches. If some high school kid with no understanding of “Porter’s Five Forces” can sell his company for $30 million, then why can’t you? Other entrepreneurs scramble to raise a few hundred thousand, but your classmate works in VC and can probably get you that cash without much hesitation. If this fails, then Goldman Sachs or BCG will hire you in a snap. This startup thing will be like a two-year vacation for you, because it only requires 60 hours of your time each week. That’s nothing. You are a machine.

But you’re not as good as you think you are.

You don’t even realize it, but you have spent the last decade training your mind to be wrong about a lot of things. You expect models to work. They are models, after all, why wouldn’t they? Improvising scares the hell out of you — and you cannot confidently follow your gut anywhere. And your network is totally useless in this world. Nobody cares about your banker friends, and your buddy in VC is only an associate, and nobody gives a shit about him. You would trade 50 Goldman Sachs contacts for one half-decent designer right now, but none of them want to talk to you. They think you are a douche before they even meet you. Never before has a tall, handsome, athletic, white man ever been so discriminated against. You moved to San Francisco — it’s one-tenth the size of New York — and yet you are totally lost.

You didn’t go to college, because you didn’t need to go to college. You made $140,000 in salary when you were 19, and when you go to Sightglass for coffee, half the people there know you. You have been mentioned in TechCrunch three different times. None of your startups have been big hits yet, but one of them was acqui-hired, and you used the proceeds to buy a condo in Hayes Valley. You are doing consulting work for $160/hour while you think about your next venture. Debt — as a concept and a reality — has never even occurred to you. Best of all, your pleasures are cheap, and you live a healthy lifestyle.

But you’re not as good as you think you are.

As much as you want to change the world, it’s probably not going to happen. Because there are a lot of mundane things that you consider to be beneath you, and those are the things that have curtailed your success to date. You have let legal paperwork screw you over twice now, and you still don’t review things that you sign. One of your co-founders was able to hijack your second startup from right underneath you, because he had the investor relationships — even though you had the right vision. When your father, who made millions doing something with trucks or shipping or whatever, gave you advice, you ignored it. What did he know about cloud platforms? Oh, and whenever you fail, it seems to have no negative impact on your bank account... in a perverse way, you are overly prepared for it.

To your credit, you became a "somebody" in Silicon Valley, when all of your friends were dreaming about Hollywood. You started a blog before everyone was blogging, and you have Tweeted a dozen times per day since 2009. Your army of social media followers likes what you have to say, and so what if half of them think you are hot... being sexy is lucrative. You are a marketing consultant with no shortage of clients, and you get invited to tech parties constantly. It’s your job after all. You hold equity in ten different startups from when you helped them in their early days, and one of them is going to cash out soon. You wrote a guest post last week that went to the top of Hacker News. In the last year, you’ve gone on dates with two different "paper billionaires," but that doesn’t matter, because you plan on getting rich from your own endeavors.

But you’re not as good as you think you are.

This town is an ecosystem, and you play one of the least critical parts. When times get tough again, nobody will want to pay for social media consultants. You have made your face into one of your key assets, but it’s an asset that will ultimately depreciate with time. And one stupid PR crisis could end your career. Sometimes you wonder how much the people in your network actually value their relationship with you, and on a few instances, you have found out the hard way — once you stop Retweeting them or writing about them, they’ll find somebody new who will. Plus, isn’t it a little bit ironic that you spend 14 hours a day talking about technology, even though you really don’t know that much about it? You may not think it’s superficial. It may not be superficial. But your ever-growing army of critics will always think it is, and you have created a world where perception overpowers reality.

You are not as good as you think you are.

[Illustration by Hallie Bateman]