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An Open Letter to My 15-Year-Old Self Just Before the Start of High School

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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,



Photo by Joe Del Tufo
George August 3, 2015 at 2:58 am

Wow. I like most of your posts, but this one just blew me away! Every paragraph seems to hit the nail on the head. I especially like “We all take turns being humiliated. Be graceful when it’s your turn, and be kind when it’s not.” Time to put these into action :-D

David Cain August 3, 2015 at 8:53 am

Thanks George. Humiliation is deceptive–it always makes us feel like it only happens to ourselves.

thisbliss August 8, 2015 at 10:59 am

And humiliation can be useful too like a remorseless scyhthe to a bloated ego!

Chaitanya August 3, 2015 at 4:28 am

What a great post David.

“…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.”

“We all take turns being humiliated. Be graceful when it’s your turn, and be kind when it’s not.”

Thanks for these great lines.

David Cain August 3, 2015 at 8:52 am

Thanks Chaitanya.

Minikins August 3, 2015 at 5:03 am

Thanks David, I will forward this to my soon to be 15 year old son and see what he thinks! It is a difficult age and I think young people are missing the feeling of safety that allowed my generation to get out there and do a lot more stuff. I certainly do not wrap up my boys in cotton wool but prefer being honest and this is an honest letter indeed.

David Cain August 3, 2015 at 8:55 am

I hope it is helpful to him!

trillie August 3, 2015 at 5:06 am

Wow! This is pure gold!
I could quote every line of this, but I’m gonna go with this one: “Like all important choices teenagers must make, you need to be at least thirty to get it right.”
And it’s not cynical at all. It’s beautiful.

David Cain August 3, 2015 at 8:56 am

Heh… right now I’m trying to see what decisions I have to make now that are better suited for my sixty-year-old self.

Dahlia August 3, 2015 at 11:57 am

I could give you a few pointers on what to include… I just had my 69th birthday… I am sending this letter to my 15 year old grandson as we have had many such conversations.
Hint: On decisions one makes for their sixty-year old self… Ask a LOT of questions, if you are not happy with the answer, ask a different question. Ask all the time: What’s the worse that can happen? And, for heaven’s sake, don’t take yourself very seriously! It’s gonna be just fine!

David Cain August 3, 2015 at 2:03 pm

I appreciate it Dahlia, thanks!

mike August 3, 2015 at 6:05 am

I smiled all the way through this post. superb.

David Cain August 3, 2015 at 8:57 am

Thanks Mike.

miss agnes August 3, 2015 at 7:42 am

So incredibly true. I remember these years and these feelings of inadequacy and humiliation: I was always too small, too nerdy, too unsexy…Years later, at a reunion, I just realized how all these people I thought were cool had turned out to become incredibly boring. I keep telling my 13 year old daughter another truth: in ten years time, you will not even remember their names. Add another ten and you will have even forgotten their faces.
Love your paragraph ” Get over any desire to be normal.” I have copied to share with my kids every time they will feel different.

David Cain August 3, 2015 at 8:58 am

I really wonder if there’s a reverse-coolness effect, where people who felt on top of things in high school are more prone to feel out-of-sorts in adulthood, and the kids who had a hard time in high school learned the things that they needed to learn to get along okay later on.

Donna August 3, 2015 at 9:42 pm

Been a reader for a couple of years and this particular article resonated so much, even though I was never a teenage boy. I felt a lot of the angst you described from my teenage years, right through my 20’s. I turned 40 last year and I’m the most comfortable with myself now than I’ve ever been. I do believe the best is still yet to come.

Here’s an interesting article on the topic of popular kids at school:http://www.dailymail.co.uk/sciencetech/article-2656133/Revenge-geeks-Cool-kids-school-popular-competent-successful-adults-peers.html

Cindy August 3, 2015 at 9:00 am

Forget high school, I wish I had gotten a letter like this before I went off to college. My favorite line: “Like all important choices teenagers must make, you need to be at least thirty to get it right.” This one is oh so true.

David Cain August 3, 2015 at 9:31 am

A time machine would solve all of our problems.

Nan August 3, 2015 at 9:09 am

Good article for the most part. You lost me a bit referring to grocery store work as a “shitty job” . It is a good job with opportunities and challenges. Yes, we even have to use our brain power on occasion. The pay is good and so are the benefits. We are all not uneducated losers . I for one, am offended and saddened that you consider any work that a person takes pride in and enjoys ,” shitty”. I believe it goes against some of your earlier articles. After all ,we can’t all have “cool” jobs !

David Cain August 3, 2015 at 9:29 am

I think you are reading too much into it–remember, this is a letter to myself. The line of work is not important; I didn’t mean to attack any particular industry. What makes a job shitty is not the type of business but how it relates to what is important to you. Any job done for years is an enormous amount of labor, and if you find it meaningless then it will drain you until you move away from it. I found grocery work deadening, but I can only speak about my experience. If you take pride in it and don’t find it draining then you already have everything I didn’t.

Trish August 3, 2015 at 9:55 am

Thanks for this. As a 34 year old just embarking on an education I wish I had started 15 years ago, it really hit home. I suppose I can be a little more kind to myself in this process.
This post and the one you wrote about “friendship” are my two favourites.
Thanks! Trish

David Cain August 3, 2015 at 2:08 pm

I am 34 too, also just beginning my studies in what I should have done all along. I think part of the absurdity is that we think we should get everything right the first time.

Martin August 4, 2015 at 11:31 am

Great point, I’m in the same boat as both of you.

I very much enjoyed reading this letter. It certainly makes me feel less bad about some of my ‘regrets’ of youth, but, as you said, it’s hard (impossible?) to make the right choices when you don’t know what you don’t know.

Paige August 3, 2015 at 10:34 am

You lost me at the “empty eyes of your manager”. We are a family that survives on my husbands retail managent position. We teach our kids that there are jobs for everyone, not everyone is meant to be a doctor or lawyer, we need grocery store workers and burger flippers. The important thing is to do your job-whatever that may be- to the best of your ability. Take pride in what you do and do it well.

David Cain August 3, 2015 at 2:12 pm

I’m sorry if it came across as maligning all managers everywhere, that really wasn’t my point. I think most of us can identify with working jobs we hated, working for a manager that does not respect you or share any values with you. Again, this is a letter to myself and I was thinking of a particular person.

Randy Hendrix August 6, 2015 at 1:45 pm

Hi David…you didn’t come across that way to me. As someone who started out in grocery stores right out of high school then ended up in college at 35, I know exactly what you’re saying.

Free to Pursue August 3, 2015 at 10:58 am

Isn’t the greatest gift is the realization we’ll never have it all figured out? As I learn more about what it is to live my one wild and wonderful life, I find I’m always left with more questions than answers and that disparity, it seems, only grows. Maybe true wisdom comes in the ability to surrender to the fact that we’ll never have it all figured out.

Tracy August 3, 2015 at 1:24 pm

Free to Pursue, I was about to make a similar comment when I realized that you had beat me to it. Somewhere around my mid-thirties, I thought I had things figured out (which was very comforting, I admit!) but in my forties I began to realize how much I really did not know. I think this quote sums it up:

“The beginning of wisdom is found in doubting; by doubting we come to the question, and by seeking we may come upon the truth.”

― Pierre Abélard

David Cain August 3, 2015 at 2:15 pm

Yes! What a relief. The goal of mastering adulthood has always been impossible. Always more questions than answers, nothing is ever black and white.

Laura B. August 3, 2015 at 12:11 pm

Thank you for this David. My son is only 7 but I am saving this for him.

Sally August 3, 2015 at 4:41 pm

Wow, you hit the nail on the head, David! Absolutely accurate. I have to pass this on to my son before he reaches high school. Thank you!

Julia August 3, 2015 at 5:03 pm

Wow – this article blew me away! Each paragraph is full of wisdom, great insight, and honesty. Not only are you a brilliant writer, but you are wise beyond your years. Thank you for sharing your gifts with us. You are a true inspiration!

chris August 3, 2015 at 5:03 pm

love this one!
on a very different note: i really appreciate the way you put quality over quantity within your blog. it makes every text worth reading!

Eugenio Perea August 3, 2015 at 6:44 pm

This is fantastic. I have the feeling that this would make a brilliant video: narrated over a few static images, much like ‘Wear Sunscreen’. I have no doubt it would go viral. I would change the Canadian Tire reference to something more universal.

Barbara August 3, 2015 at 6:47 pm

Hi David. You do indeed write about what school never taught. If more educators read and reflect on your writing, and change up their game, then perhaps that may become a byline you will have to change. I have a grandson moving into these realms of experience. I know we will enjoy discussing the content you’ve addressed here. Thank you.

Luciana August 3, 2015 at 9:19 pm

What a great post. Reminded me of Cat Stevens – Father and Son. Trying to give the child some sense of freedom to be and to pose questions, hoping to be laughing with happiness at the lack of sense of it all instead of laughing in despair.

Hilary August 4, 2015 at 7:54 am

Great post.
One of the best things that happened to me at age 16 was that our widely revered English teacher threw my dog-eared thesaurus out the window (literally) one day and said I got to use it again only when I knew and could use well all the regular words, first. Even at the time I had an inkling that he was right. He was so right.

Justin August 4, 2015 at 9:01 am

This is probably your best post yet. I feel like we went through a lot of the same things in high school. Probably everybody did, but for some reason it didn’t feel that way that the time. I’m saving this to give to my kids when they’re teenagers.

Joyful2bee August 4, 2015 at 10:18 am

This is just plain brilliant!! I saw a lot of this while watching my sons grow up. Thank you for a delightful insight into male maturation. Loved this!!

Chris August 4, 2015 at 10:21 am

This is really nice and thoughtful. I just sent it along to my brother (sophomore in college). I wish I had read this at that age but I’m sure it wouldn’t have done any good. I’d probably just say “I know all that already” and then went on continuing to be a jerk and spending all of my money on video games and bad food.

David Cain August 4, 2015 at 4:25 pm

Haha… I would have done the same thing. Youth wasted on the young again!!

thisbliss August 8, 2015 at 10:57 am

Great article. This is the irony that this letter would undoubtedly get lost in all the noise bombarding a teenagers mind. It probably takes constant repetition and reassurance of these ideas from an earlier age by family members and even then!

Jim Haungs August 4, 2015 at 2:29 pm

David, from all the erstwhile 15-year olds, you are, hands-down, the brightest light on the planet. Thank you.

Bubba Jr August 4, 2015 at 3:45 pm

Fantastic post! I appreciate the effort you always put in.

I hope I can be 20% as eloquent and thorough when my son starts high school.

Manpreet Singh August 4, 2015 at 4:02 pm

“Find those grooves of meaning that you can follow into adulthood.”
Beautifully written! And a great article, not just for 15-year olds ;)

Joseph August 4, 2015 at 9:33 pm

One of the best things I’ve ever read. Thanks!

Edward August 5, 2015 at 2:23 pm

Nice! Love the “customs and norms” bit. Mine would have been pretty short, I think…

“Dear self-absorbed dickhead,
I’d tell you what to do differently but that would probably screw us both up. You’re generally on the right track (especially with music) and things turn out okay-ish. There’ll be a time when you get drunk with your friends and decide it’s a good idea to climb a statue. …Don’t do that last bit.”

David Cain August 7, 2015 at 9:10 am

Don’t forget to be gentle!

StephInIndy August 6, 2015 at 6:05 pm

i was a little disappointed to hear of your 15-yo self’s view of women, and hoped to hear something a bit more profound about the other gender from the learned self…apart from just don’t compare yourself… :-/

David Cain August 7, 2015 at 9:10 am

I’m not sure what you’re referring to exactly… can you elaborate?

LennStar August 7, 2015 at 2:35 pm

We can only understand life backwards, but we must live it forwards.

Trevor August 9, 2015 at 1:20 pm

Even at 27, I really needed to hear this! Thank you.

Luna Darcy August 9, 2015 at 3:41 pm

Hi David,

Absolutely love this!

Made me reflect and I realize most of what you stated here are true, even today.

Loved your pieces of advice, especially the bit about not trying to be cool. I made that mistake and it landed me to parts I didn’t want to be in the first place, but of course I didn’t know it then.

Thank you for such a pensive post.


Becky August 12, 2015 at 7:24 am

Wow, this was amazing! So insightful, so true! Thank you so much :)

Laura Beth August 15, 2015 at 4:08 pm

Well David, what can I say?

You have a knack for conveying your viewpoint in a way few other bloggers do, and that’s why I continue reading you.

From a financial standpoint, I liked your comment about doing the least long-term damage to your finances as you’re trying to figure our what to do with your life in your 20’s.

Great post!
Laura Beth

Len August 16, 2015 at 2:14 am

“You will also experience a weird and creepy pressure to be manly, including how you position your legs when you sit ”

Did you feel some sort of pressure involving how to position your legs in an effort to manly? As in spreading them wide or something similar?

It’s funny you mention it, as I have an issue with my legs which means I find it incredibly painful to cross them, or to drape one leg over the other. As a result, when I sit down my legs don’t come together – they’re always open.

I have often been accused of intentionally spreading them when I sit, and some have taken it as far as erroneously thinking that I’m trying to “assert my dominance” or “protect my territory.”

Go figure…

Brad August 17, 2015 at 1:16 am

This is a mind bogglingly awesome post and feels like it was directed straight at my 15 year old self. Your point about girls resonated strongly, that wasn’t a lesson I learned until college. Having gone to a single sex school I spent most of my time too scared to talk to any girls I came across anywhere else.

ثبت شرکت August 19, 2015 at 1:35 am

good letter

Stephan September 2, 2015 at 8:03 am

This is again one perfect post. I don’t know how you do it David but what you say seems so true and real for my own 32yo life… I only can learn from this retrospective. A big thank you for that!

Anca September 5, 2015 at 12:45 pm

I just sent this article to a 15-year-old girl who tried to kill herself the other night, for the same reasons your 15-year-old self felt tormented. It gave me the chills – I hope it gives her good ideas. Keep writing David!

Peter November 11, 2015 at 5:05 am

Hi David,

what a cracking article! I hope you don’t mind but I’ll be using this with the young people with whom I work. Might tweak the grocery store section a bit but the comment on Customs and Norms tickled. Currently trying to work out the personality changes that have come about from listening to Blu Cantrell.

Joseph November 13, 2015 at 10:56 am

Perhaps, if people had Jesus in their life, they would not be asking so many questions and worried about so many things. All the answers are right there, but people with these concerns don’t seem to go to church, read the bible and live it everyday.

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