Hey, tough guy: a letter to myself.

[Which We Want flannel from Need/Supply + All Saints Assembly leather jacket + Rag & Bone hat + PAIGE Hoxton jeans + Sigerson Morrison booties + Vanessa Mooney spike necklace + Warby Parker Nash glasses.]

Dear Carey, ages 6-16:

Yo.

I say ‘Yo,’ because I know this to be your salutation of choice. You wrote it in the margin of a 1987 Ladies’ Home Journal three-page chicken recipe guide that was mom’s, which she photocopied for you before you boldly moved to Chicago, and still use. I also know that you like to say ‘Yo’ because you’re a tough guy. You watch Beavis and Butthead and The Hunt for Red October and listen to Dr. Dre and smoke stolen Benson & Hedges and taste Bombay Sapphire out of the bottle cap while your friends watch 90210 and get highlights and listen to Spin Doctors tapes.

Don’t take this as criticism; who doesn’t want to be tough? More so, who wants to be the opposite of tough? No one. No one at all. Especially not you. But I’m here to tell you tough isn’t going to come along with foul language, Umbro shorts, that weird, practiced swagger on your cherished hand-me-down dirt bike from your brother, or by being mean. The opposite. But we’ll get to that.

By now, you’ve absorbed tough through a few different avenues: meanies, Dads and scary Moms; jock chicks; movie characters; that one boy (FYI you still know him at 33) who, at the church lock-in said he was going to take [name withheld] into the closet and squeeze on her prematurely monstrous 7th grade boobs; boys in general, really; the neighborhood boy who threw your bike in a mud puddle for no reason (FYI you no longer know him, but Facebook shows he has grown hugely fat and bald, yay); and your brother, when you’re not kneeing him in the nuts by accident while jumping on the bed.

Some of these are viable role models. Most of them are not. Dads and brothers are viable. Scary Moms are you in 30 years with 4 times the insecurity. Jock chicks are indiscernible weirdos; they’ll only have that narrow advantage for so long, so let them languish in it. Movie characters were written to scare you. Only pay attention to the unassuming boys (they turn out best; the other ones are peaking right now, trust me). And meanies… well, I’ll let you figure them out on your own. Don’t worry; you’ll triumph. And though you’ll run with a few, you won’t ever be one.

You’ll try to be tough almost endlessly. Mostly, it will backfire. Sometimes, it won’t: Calling a spade a spade takes toughness, but it will pay dividends. Meeting challenges head-on (like the time you miss all of the final exam prep to go to Vancouver with Mom and Dad, but you take the tests and kill them anyway) will require you to sack up and it won’t be fun. Basically, folding your tough inside is part of growing up. Putting it on other people is not.

You’ll waver at times between which is better: tough or funny. Don’t make a choice yet.

If I could give you advice, it’d be: shoot for calm, quiet stoicism; cry at home. Pick one swear word, own it, and make it a good one. (Spoiler alert: you’ll pick “Goddamnit.”) Listen to music you like. It won’t be what everyone else likes. Often, it will be your parents’ vinyl. Wear clothes you’re comfortable in. Drive like you’ll never get pulled over. (You will. 9 times. Only 3 tickets.) Stop showing off your rebellious proclivities in class and pay attention, especially when your mom is substituting. Look scary bitches in the eye. Keep a good quip or two in your back pocket.

The good news? For every time you try to be tough, you’ll be humbled 4 times over. You’ll learn quickly.

You’ll want to be tough almost more than you’ll want to be sexy or alluring or clever. (Spoiler alert 2: you’re still clinging to this question at 33, but clever has proven to be much more fun.) Tough has to have a purpose. Look at it like a problem/solution matter—this is your future professional self talking. Address the problem with a solution, and if tough works, work it. But blanket tough is tiring. I’ll let the guys you hurt along the way prove that, since I know you don’t believe me.

Can we also just prevent a few of the most cringe-worthy events of all time? The afternoon on the swing set in the backyard when you taught your best friend every single bad word you knew, then mom washes your mouth out with soap? Dude, whisper. Don’t count the number of times your classmate says “Um” during her presentation in 6th grade art on your fingers for everyone in class to see. It felt so good—comedically brilliant, really—but you’ll hate yourself for it. That time you’re kicking the soccer ball around with your soccer star brother in the backyard and want to try the word “f*^king” on for size? Don’t. It was totally humiliating. The time you snuck the “What’s Happening to my Body” book into the prepubescent boy’s backpack in the library so he’d set the alarm off when he walked out? Please, please don’t. Deafening your carpool every morning with Tupac so you didn’t have to talk to them? C’mon.

Listen. I know why this all happens. Because you’re just a big softy. Almost every time you were soft, from 6-16, it burned you. Somewhere down the line, though—and don’t rush it—you’re going to be so glad you are.

Anyway, you’ll eventually have this totally badass, buttery soft, cut-to-perfection, mean as hell leather motorcycle jacket you that can throw on whenever you feel like pretending otherwise.

Now, go hug your mom.

-C.