Why WAs this guy not rolling in sex?

Everyone Reading This Hated High School

Wil Shipley
3 min readFeb 4, 2013

I’ve learned not to talk about my school experience with other nerds because it inevitably turns out we’ve had slightly different variants on the same basic crappy time, and—nerds being natural one-uppers—the conversation becomes a competition for who had the worst time. “The jocks were cruel to me.” “Well, all the kids were mean to me.” “The teachers hated me, too!” It’s a peculiar kind of fight we’ll call a “sad-off,” the winner of which is the one who enjoyed the most misery. Hooray.

One of the social graces I did not learn in school—in between busily not learning any other social graces either—was that pretty much nobody wants to hear you whine, ever. A sad-off, then, is the quickest way for two or more nerds to burn through all their accumulated whine credits with each other and everyone within earshot, as well. It’s a pyrrhic victory even for the one who has proven himself to be the most pathetic—which is a known aphrodisiac in no culture, anywhere.

To prevent a virtual sad-off, I’ll here recognize that you had a bad time, too, because you’re reading this and everyone here is pretty damn accomplished. Nobody who sailed happily through high school has ever gone on to change the world.

Often when strangers find out I work for myself, they imagine it to be very glamorous. “You set your own hours and pay yourself what you want?” Well, yes, except those hours are “always” and my pay is fundamentally capped at how much my company earns, which is completely my responsibility (but, hey, no pressure).

I don’t fault anyone for misapprehending my life—heck, I’ll admit that I cultivate it a bit. If you want to believe I’m a playboy, more power to me, I figure.

But almost always, these innocent strangers will add, “Geez, I should have gone into computers.” As if that’s the key. If they’d only majored in “computers,” instead of English or poly-sci or whatever, they’d be millionaires now! Everyone who speaks “computer” is rich, right?

I used to bridle at this. Now look here, I’d say:

I’m good at programming because I started doing it when I was 12 and never stopped. I missed out on everything cool in high school not because I was super straight-edge, but because I was an incredibly socially awkward loser and had no actual friends.

Being a loser in school was a blessing not only because it allowed me to practice what I love, but also because being an outsider forced me to be an individual when others are conforming to group expectations. High school is explicitly un-individual; to the extent that you don’t follow their preset program, you’re making more work for teachers and administrators.

So while going into “computers” was a very safe decision when I was a the University of Washington,I chose to work with NeXT, Inc., instead of Microsoft, which at the time was lunacy. All my friends who went “across the water” were millionaires within a year. It took NeXTstep another fifteen years to finally become ubiquitous, but I always believed it should, and would.

How do you sum up that it’s your individuality that matters, not what particular field you choose? I now tell people this:

You don’t really want to be in computers, you just want to succeed. I’ve met tons of successful and happy people: billionaire tech dudes, chocolate makers, joke writers, chefs, producers, painters. The only thing they have in common is they’re doing what they love, not what they’re expected to do, and they do it all the damn time.

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Wil Shipley

I’m the owner and lead developer at Delicious Monster Software.