A Letter to Myself

november, feels, effectiveness

One of the things I tried in 2013 as part of my getting better at life regiment was writing letters to myself, both forwards in time and backwards. The idea was to force some sense continuity to me across time and space. Or at least time. I would write a letter to myself in the future, detailing all of the things I wanted to achieve by then, and the things I thought were going to be the most important to focus on. Fast forward a month, and I’d read the letter in my temporal mailbox, reflect on it, and reply to me-in-the-past, and start the thing all over again.

I only made it three months because once-a-month habits are hard habits to build, but I fondly look back on this as one of my better ideas. I’ve always meant to get back into the habit, and I’m really scraping for ideas to write about today. So I’m going to try it. Expect heavy amounts of feels. Abort early if you’re uncomfortable with feels.

I’m not sure I can stretch out two letters to myself to the 2000 word mark, but it’s worth a try. To help me in this endeavor, I’m instead going to write out a bunch of advice to myself that I wished I had had when I was 20. And should I fail to hit my word mark, I can always phone it in and write a bullshit programming essay later if I need to. I’ve got infinite amounts of those bad boys in me.


Hey there bud. Congratulations on getting accepted into university! That’s a big move! Honestly mate, I was pretty worried about you for a while there; it felt like you had lost both your ambition and your way. But good news, university is going to be a nice clean break from your old life. You’re free to reinvent yourself as you please, and with no ties back to your old life, that will be who you are. It’s a big responsibility, to be honest. Spend some time thinking about the person you’d like to be. It’ll be worth your while, I promise.

There’s… well, look, there’s no good way to put this, but you’re a man who appreciates stark honesty. You’re a cocky little prick. I know it feels like you’ve made it big, but you’ve still got a long way to go. When you start classes, it’s going to become painfully obvious that you’re ahead of the class, but don’t let it go to your head. Your skills are impressive for a first year, but that doesn’t mean you can afford to stop getting better. Your peers will catch up with you much sooner than you’d expect – they’re all way smarter than you give them credit for – and you’re going to be outpaced very soon. Ego mate, that shit kills. If you feel like you’re the smartest person in the room, find another room. As quickly as you can.

People, man. Jesus. People are important. You’ve been able to get by on your personal skills so far, but I chose those words carefully. You’ve been able to “get by.” Here are a couple tips: not everybody is going to like the same sides of you. Get good at identifying quickly what people are looking for, and find a side of you that aligns with that. But be genuine about it. Remember, this whole “I am who I am” thing is bullshit. You’re multifaceted as hell; we both know it. Read a book on how to get along with people. Hell, read two. Really, you can’t go overboard with this kind of thing.

I know, I know, it sounds like an adult position to hold, but school man, that shit is good. It’s really good. The first two years, well, I guess you can take or leave them, but after that it gets really interesting. Pay attention when you’re there, you know, ’cause you’re paying for it either way. You’re right, marks don’t really matter in the big scheme of things, but there’s something to be said about walking out of a final exam knowing that you aced it. Knowledge is power, as the cliché goes.

Oh, and while we’re on the topic, clichés are things for a reason. There is a hugely compressed amount of knowledge to be found in them. Unfortunately, this kind of thing is only really obvious in retrospect, but maybe keep your eye on it, because paying attention pays its weight in gold. Which isn’t very much, if you think about it, but here’s another piece of advice: nobody likes a smart aleck.

Stop being so afraid to take chances! This is a hard one to learn, but really, it’s the secret to success. If you really want something, ask for it. Or take it, for some definitions of “take”. Pretty girl you want to go out with? Historically, all the women you have wanted to taken out have wanted to be taken out. You were just too shy to be the catalyst to make that happen. Want that job you’ve always been dreaming about? Turns out that the biggest thing stopping you is yourself. You never know what might happen if you apply. Spoilers: you’ll get it1. Fortune favors the bold, playa.

Hearts, mate. Those things are unfortunately way too easy to break. For whatever reason, you seem to attract those especially vulnerable to it (or maybe just everyone is), so be as gentle as you can with that trust you’ve been granted. It’s an unfortunate fact of life that you’re going to run into; hearts break, theirs and yours. Don’t let that scare you off though – when it’s good, it’s worth all the shit you had to put up with to get there. Try to keep in mind that those exes of yours are still people, and if you ever cared about them, you probably should still, even if it’s only a marginal amount. I don’t have a great solution for this one, sorry, but try to keep it in mind. Maybe you’ll figure something out, and if you do, send it my way. Thanks.

Oh hey, about that whole “find your passion” thing; it’s kinda bullshit to be frank with you. It’s all a scam perpetrated by selection bias – those for whom it worked out are incentivezed to tell you about it to validate themselves. Here’s the real secret though: you already know what you like doing. Figure out a way to make money off it. If that doesn’t work out, figure out what you’re willing to do make money, and then do that well enough to get paid.

Closely related to that point is that intentions don’t count for anything; consequences do. Doing evil for the sake of good is no different from doing evil for the sake of evil. Extrapolate from this; if your internal monologue tells you that what you’re doing is just, but it isn’t working out for you, then maybe change what you’re doing. Your internal justifications are just that – lies you tell yourself to maintain the status quo. You can rationalize any stupid position if you try hard enough, and the nefarious part is that you usually won’t notice yourself doing it. Being aware of the outcomes is your only real defense. Pay attention to it.

Be less afraid to look like an idiot. It’s going to happen to you regardless, so the wisest solution is to control the situations in which you look stupid. Be proactive about looking less stupid. If you don’t know how to solve a problem, ask someone who does. Preferably somebody who likes you. Don’t have anyone who likes you who knows how to solve the problem? Solve that problem first. But yeah, face it, looking like a fool is inevitable, so try to make it happen on your terms when the stakes are low. You’ll get burned anyway, occasionally, but ideally less than you would otherwise.

Along those lines, start hunting for wisdom. Ask people what they wished they knew when they were 20. See if you start seeing trends. You will. Listen to the outside view on this one; you are likely to be in the same reference forecasting class. Just because you feel like you’ve got it figured out doesn’t mean that you do.

Stop comparing yourself to your peers. Hopefully you’ll come out ahead in those comparisons, but that sets the bar low. Compare yourself to your superiors, and use that as motivation to get better. Set the bar unbelievably high and then try to meet it. It’s not always going to work, but it’s going to work more often than you’d otherwise think. Aim for things significantly past your grasp, and then find a way to extend your reach. You don’t get better without trying, and you can’t achieve amazing things without getting better first.

Anyway mate, thanks for listening. Sorry about all the unsolicited feedback, but if you’re anything like me, you’ll someday see the wisdom in it. Maybe. Hopefully. Regardless, you’re a smart guy and you’ll figure it out on your own. I know. I’ve been there.

All the best, Sandy


  1. I hope this doesn’t lead to some sort of temporal paradox, where I convince myself to apply earlier-than-a-good-idea, fail to get my dream job, and then never manage to go back in time to tell myself this due to overwhelming depression.