DK has tagged me to do this meme; I turned sixteen in 1997 and was, frankly, a bit of a jackass. Receiving this letter probably wouldn’t have changed that, but hey, you never know.
Having been invited by others to advise you about the twelve years to come, please find below a few tips and reassurances. I won’t say too much – time paradox and all that – but I hope you’ll find the general thrust of my advice useful.
My first tip: broaden your ambitions. I know you harbour vague thoughts about going to a small liberal arts university and becoming an English teacher. Abandon those. You’ll realise soon the virtues of anonymity amongst the hordes and warm weather – not to mention that, just in the nick of time, you’re going to realise that it’s not the ‘literature’ part of English literature you enjoy. Go with that instinct – it’ll make you happy.
You also see ahead of yourself, whenever you bother to think about it, a pretty unremarkable lifestyle, living the American dream. Well, you’re living it at the moment; think about how much you enjoy it now, and imagine what it’ll be like when you try it on your own in a couple of years’ time.
My second tip: avoid becoming materialistic. I hate to break it to you, but you’re destined for the life of a nomad. I won’t horrify you with the details of how many times you have to pack up your shit and move it. Just take my word for it that acquiring more stuff than you need is going to cause you more trouble than it’s worth.
My third tip: when, in a few years, you decide to pursue your further academic career, ignore the cost and do it. It’s not going to turn out the way you think, but it’s going to lead you to interesting places. There will be ups and downs, but persevere through the downs: the ups are more than sufficient reward.
My fourth tip, which follows on from the third: when you encounter other obstacles to your wishes, don’t give up. This isn’t an inspirational platitude; I’ve seen time and again that when you bust your ass, you succeed. In time, you will come to regard this quality of yourself as a kind of mystical power. Just remember the converse is also true: when you don’t bust your ass, you fail. And you will fail. More than once. The greatest of those failures will come in November 2000. Ride it out: it’s your threshold to adulthood, and between you and me, you dodged a bullet there.
Finally, a word about men. You go out with anybody who asks, and you aren’t afraid to be the pursuer. People will frown on this, but keep it up. Every loser you date because you like the look of his cheekbones, or because he made an intellectual remark about philosophy, is going to provide you with valuable learning experience. And one day, via a series of random and unlikely-in-retrospect events, you’re going to come across a man who combines the best in cheekbones, intellect, and various other qualities you’ll come to value. When circumstances bring you to his attention, remember my fourth tip.
Oh – and in 2002, keep your eyes open for a conjunction of Latin and libertarianism. You’ll know it’s coming up when a total stranger insults you gratuitously in public. That incident will change your life.