Dear 15-year-old self,

The first thing to know is that high school, and everything that comes after it, is impossible to get right. When you’re a kid you don’t have to be anything except what you are, a kid. But when you’re an adult, or training to be one, all aspects of life seem to become concerned with trying to be a certain way: sufficiently cool, successful, independent, respectable, charitable, productive, original, normal, healthy, sexy, or whatever else you currently are not. This impossible goal is the great joke of human life that I will try to explain in this letter.

In high school, this mostly means one thing: don’t try to be cool. You will not be cool until your late twenties. It isn’t actually possible to be cool in high school—all high school students are hopelessly uncool, especially the cool ones. This will be obvious the moment you graduate, but in the meantime you might have to make a point of remembering it.

None of the respect you earn in high school will buy you anything after you leave high school. It’s like working at Canadian Tire for a summer and getting paid only in Canadian Tire money. Waste no energy earning respect in high school. Spend it instead wandering every sidestreet of geekdom and subculture you pass by. Instead of finding scraps of approval from uncool people, you will end up finding something real and lasting in Brian Eno or Nietzsche or Margaret Atwood or Public Radio. Find those grooves of meaning that you can follow into adulthood. When people give you a hard time for liking what you like, that’s a sign you’re on the right track. You are uncovering veins of precious metals; they are scrounging for nearly-expired coupons.

Get a shitty job. Work in a grocery store, steering shrink-wrapped pallets of cola through cramped warehouses. Spend hours daintily arranging shelves that you will later see customers destroy in minutes. This will pay for your food court lunches and headphones, and also impress on you the nihilistic reality of most of the work out there. Get a good, long, nasty look at how impersonal and irrelevant your role on this earth can be if you’re not careful. Get your face right into it, right into the filthy shelves and bins of expired yogurt and the empty eyes of your manager and make a vow that whatever you do with your life you will always be moving away from all of that. 

Go to class and learn the material, not for the material’s sake, but so that you can learn how to learn things, and how to admit it when you don’t understand something. You may never need to understand chemistry but you will eventually need to know how to ask for help, how to remember things with analogies and pictures in your head, how to write readable sentences, and how to care a little bit more about what you produce than the people around you.

Your choice of a post-secondary path—you won’t get this right either. Like all important choices teenagers must make, you need to be at least thirty to get it right. No seventeen-year-old has any real idea who they are or what they’re doing. The only strategy is to do new and interesting things as frequently as possible, trying to find those veins of meaning, doing as little permanent damage in the meantime to your health and your finances. There is enormous pressure to get this choice right, and you won’t.

The most cost-effective and useful post-secondary program is probably a solo backpacking trip. People mature at double speed when they are fending for themselves in foreign countries. You can get wiser and younger at the same time. This is a loophole in human development, take advantage.

You will probably avoid talking to girls because you’re afraid they won’t like you. What will happen is perfectly ironic and I hope you will find it funny one day—they won’t like you because you won’t talk to them. Love and affection operate by a very simple rule: people like the people who they feel good around. Shy people are scary to be around because they are a big bundle of question marks. Nobody knows what they can say around shy people, so they avoid them. It’s anything but personal–when it comes to other people’s impressions it’s never about who you are, it’s about how they feel.

People get with others for their superficial attributes, but stay with them for the deeper ones. So don’t think your hidden deeper qualities are enough. Smiling matters. Small talk matters. How you dress matters. Don’t neglect those superficial qualities—they are the access port to your deeper ones. If you think that’s unfair, you’re wrong, because you do the same thing! Try to laugh at this.

You will also experience a weird and creepy pressure to be manly, including how you position your legs when you sit and how often you use swear words. In reality, there are no men in high school, but it is hilarious to watch them pretend. Be the one who gets the joke. Part of the typical boy’s act is to convey a certain dismissiveness whenever they talk about women, as if we all know that a woman is just a kind of failed man—too sensitive, too needy, kind of dumb. You’ll know it when you see it, I hope. Years later when you are managing a business you will recognize this act as lazy attempt at what marketers call “positioning”—I must be a man because I’m not a woman. Instead, practice manliness without any comparison to women: go lift some weights, build things, invent things, wear oversized clothes that don’t match, and ignore your detractors.

At some point you will be humiliated. You will fart at the wrong time, maybe only figuratively. Someone will call you out on something and the room will go quiet and you’ll say something to make it worse. The weird thing about humiliation is that we fear it because it makes us feel like an outsider, as if it proves we’re uniquely incompetent or ignorant. But humiliation is as universal as it gets. It proves you’re in the big boat with everyone else, not alone in the dinghy. We all take turns being humiliated. Be graceful when it’s your turn, and be kind when it’s not.

Get over any desire to be normal. The desire to be normal is its own perversion. Some people do achieve the appearance of normalness, which means they have successfully hidden or beaten down everything about them that is interesting or memorable in the hopes that they become impervious to criticism. Go the other way. The great joke here is that nobody has ever been normal.

The bottom line, the thing that will protect you from the horrors of adulthood, is to keep remembering that it’s all completely absurd. The customs and norms you’re supposed to follow are really a random pile of mismatched leftovers from centuries of medieval courts, tribal initiations, R&B songs and romantic comedies, with a large dose of reptile brain making it seem really serious. Don’t believe it! The more seriously you take it, the harder you will laugh when you remember.

This all may seem cynical, and I guess it is. But I am saying it to help you be more gentle. It is pretty funny that you can never know what you need to know without your future self writing you a cryptic letter, which can’t actually happen in real life. The great joke is a crude and often offensive one, and at times it will hurt you and people you know. But you’ll remember the punchline, sometimes, take the long view of things, and find the beauty and humor in it in the end. I know this because I know you very well.

With love,

David

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Photo by Joe Del Tufo