What would you say to your 17-year-old self?
That is the question with which stacy-marie ishmael closed out the most recent edition of her newsletter, the very excellent The Main Event. For the context driving the question, you will need to read the newsletter. Which you should do anyways; it’s really quite good.
I read this edition of The Main Event as I typically do, early on Monday morning, while slurping coffee and desperately trying to activate for the day. It apparently caught me in a reflective mood, because I did something I almost never do: I wrote back. stacy-marie sent me a very kind note in return, which I’m not going to share, but I will share what I sent to her, in an expanded version.
This missive to my past self started off pretty sincere, but it didn’t feel right. Then I thought about what I honestly knew about 17-year-old Josh, and took a slightly different tack. It went a little off the rails, but eventually made it back to sincere-ish. This time, though, it felt authentic. Here you go.
Look, kid, I don’t know how long I have, so we need to make this quick. Yeah, I’m future you. Hola. I know you believe me because this is the sort of shit you spend a distressing amount of time thinking about. But in case you have any lingering doubts: remember that time [a highly embarrassing memory we will take to our grave and is thus redacted]. Right, yes, this is a real Back to the Future moment. No, you don’t need to recite your favorite BACK TO THE FUTURE 2 quotes to — no, I just said — look motherfucker, we don’t have much time, so I’m begging you: please, shut the fuck up.
First things first: here are the winning Powerball numbers for the next five years. High-dollar prize winners only. After you win, you tear this list up and you never, ever play again. You hear me? You don’t want to risk drawing the attention of the wrong people by winning big twice. What do I mean by…? Well, if I’m able to do this — talking to my younger self — then presumably other people can and have also. Since you don’t regularly read about some asshole from Iowa winning ten Powerballs in a row, it follows then that there is a secret watchdog organization whose sole reason for existing is to watch for these types of anomalous patterns and snuff them out. Better to play it safe. Which means: Don’t. Get. Greedy. Now, once you have your winnings, you’re going to start making some modest, relatively speaking, investments. Here’s a roadmap to follow. Again, the goal is to fly under the radar. You play this smart and do it right, before long you’ll be living someplace warm by the ocean, with all the time in the world to write, and maybe the means to do a little good in the world. You don’t care about that last one right now, but down the line, you will.
Now, that mercenary but necessary bit of business out of the way, if there was time, I’d also tell my 17-year-old self
If you fuck this up — and let’s be real, you have a wobbly moral compass, so-so impulse control, and an unfortunate predilection for thinking you’re the smartest person in the room — so there’s every likelihood you will fuck it up — it’ll be okay. You — we — have a good life. You’ll find your people, even if it takes til you’re almost 30 for it to happen. You’re going to become comfortable in your skin in a way you never believed possible, like your skin is a perfectly tailored suit. You’ll paint your toenails lavender and ocean blue and people will compliment you on it. You’ll call out strangers for not washing their hands after using the bathroom (yeah, we still get icked by lack of basic hygiene and sanitation). Your hair will start going gray in your thirties, but at 41 it will still be thick and luxurious. You’re also going to bleach it soon and go platinum blonde. (You haven’t started watching Buffy yet, but go to Lycos or Altavista or whatever and search for “Spike on Buffy.”) You won’t have kids (right? no clue how we managed to pull that one off) but you’ll become a dog person at the age of 38 (who knew?) and they will become one of the best parts of your life. You’ll blunder your way into a career that isn’t writing; one that not only pays well but that you also enjoy. (Spoiler alert: You’re gonna spend a lot of time in the Excel mines, moving numbers around on spreadsheets.) Speaking of writing: you’ll publish your first short story — in a reputable publication, no less! — and get paid quite a bit of money for it, and strangers will send you nice messages about it. This one’s a bummer, but the scourge of depression will discover you like it’s Christopher Columbus, and for a while, things won’t be easy. Most of the time, though, it will be manageable and better days will be ahead. I won’t tell you to be patient, because that is not a quality either of us possesses in much quantity, but fuck it: try to be patient. Enjoy being young. Take risks. Make mistakes, and try to learn but, ideally, not die from them. Take no shit. Stay curious. Keep writing. Please don’t fuck up this lotto thing.
Now it’s my turn to ask: What would you say to your 17-year-old self?

‡
Since this one is already running long, we’re going to end here today. The normal reading/watching/Kirbying stuff will come out in its own shiny post later this week.