You Can Stop Checking Off The Boxes Now

Jacqueline Dooley
5 min readJun 20, 2022
My daughter at her senior prom — Photo by author

It seems to me, looking in from the outside, that high school has been all about big achievements. It was four years of pushing you relentlessly forward, even in the midst of a global pandemic. There was barely time to celebrate any single success before the next school year, then the next, and on and on until graduation.

And now…what? College for you (close by) and work (maybe) and, good lord, a little time off from all these damn expectations — time to reflect on the direction you want to go without all of us breathing down your neck.

You get to decide what comes next. You don’t have to fit into anyone’s idea of what you should be or do or achieve. We’re pretty much making all of this crap up anyway.

I hope you don’t feel like a failure if you don’t check the boxes you think you should check or become the person you think everyone wants you to be.

So yeah, high school has been all about meeting expectations — mostly other people’s. I’ve watched you do the work and not do the work. I’ve helped you arrive on time, prepare for tests, weather the stress of unrealistic deadlines, and retreat to your bedroom, defeated.

I’ve seen you disappear into the crowd as an overwhelmed freshman and reemerge as a (somewhat) fully formed senior. But, let’s be honest, no one is fully formed at 18 and that’s fucking fine. You’re so damn young. Was I ever that young? It seems impossible and exhausting and unrealistic that there’s now an entirely new set of boxes for you to check.

Fuck that shit.

The world is a vast and hostile place. I’m not sure what advice I can give as you prepare to graduate from a school that has given you very little guidance and almost no preparation for how to manage what comes next. But, I can tell you what I’ve learned after half a century of life and that’s to throw the damn boxes away. I know that’s easy for me to say.

It must seem like a mixed message. You’ve spent your life checking those boxes, meeting the expectations of the adults and sometimes paying a very high price for that. We’ve burdened you with our own ideas of what your life should or could look like and the result was a childhood of looking ahead to the next milestone or achievement or school year. The American dream and all that nonsense.

I’m sorry that we put so much pressure on you to achieve the things we thought you should achieve. Was it for your own good, or ours? Was it to secure a happy future? Some people might say yes but you’re old enough to know that no one can promise you happiness.

I think, probably, the last 12 years of your life were more about what we, the adults, wanted for ourselves than any goals for your future. Even so, you came this far. You’re graduating.

I’m proud of you for getting this far, especially after going through so much: the death of your sister, the transformation of your face, the shattering of your mental health, a pandemic that kept you locked in your room for most of tenth grade and all of eleventh. You’ve emerged from some of the darkest days more determined than ever. But I know you’re tired. I know you’re sad.

I promise you, sweetie, you don’t have to pretend to be happy for my benefit. I hereby release you from carrying the burden of my own happiness.

You also don’t have to have a clear picture of what comes next. I’ll tell you a secret: no one knows what comes next, not even the people who think they do.

I hope for so much when it comes to your life, but mostly that you live it your way without apology or guilt or shame. I hope you change the world, but only if you want to. I hope you take naps and make art and surround yourself with people who love you fiercely (and who you love just as fiercely).

I hope you remember to call me once in a while.

You haven’t failed me — or anyone else — if you don’t manifest into the person we think you should be. You don’t even have to manifest into your own dream of yourself because, and I can’t stress this enough, you’re 18 years old. This is only one of many versions of yourself.

We can plan all the things and check all the boxes and we can still get struck by lightning. The rug, as they say, can (and probably will) get pulled out from under you and then you’ll have to start all over again. Sometimes you or someone you love gets sick. Sometimes the brakes fail. Sometimes a hurricane flattens your house. Sometimes the world shuts down because of a global pandemic.

You can’t really plan for any of this stuff, but the one thing I can say with absolute certainty is that shit will go wrong.

I don’t mean to sound cynical. My advice isn’t meant to be fatalistic or bleak. I’m not saying you shouldn’t have goals or dreams. What I’m trying to do is let you off the hook (just teensy tiny bit) because life is chaos.

I’ve seen you handle disasters with grace, determination, and flexibility. That’s what gets you through to the other side of hardship. Well, that and the people who love you.

Resilience. This is the skill you’ll need to take with you into the next chapter of your life. It’s the skill that not only helps you survive the cataclysm of unexpected change, but it can ultimately help you land safely — and happily — on the other side of whatever tsunamis turn your life upside down.

I have nothing tangible to offer, no words of grandiosity, no clear guidelines to see you through to some kind of perfect ending. But I have endless faith in you. I have endless love. I am astounded by your intellect and curiosity and remarkable creativity.

You’re a fledgling. It’s a scary role to play because the world is full of danger. It’s incredibly easy to fall or get lost. I have faith in you. I hope you’ll astonish yourself with how capable you are. The truth is, you astonish me each and every day. It’s my job to remind you (often and without judgment) that you’ve got this (and, maybe, sometimes you don’t — but that’s okay too).

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Jacqueline Dooley

Essayist, content writer, bereaved parent. Bylines: Human Parts, GEN, Marker, OneZero, Washington Post, Al Jazeera, Pulse, HuffPost, Longreads, Modern Loss