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‘Dear future self’: Read our high school essay contest winners

We asked teens to imagine it’s 2030 and write letters to their future selves

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December 23, 2019 at 3:19 p.m. EST

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Illustrations by Vero Cerri.

The first few weeks were bleak.

In October, we contacted writing programs and high schools across the country about an essay contest: The Lily wanted high school students — girls and young women — to write about their lives for us. The prompt?

We didn’t get a single entry for a few weeks, and we started shaking in our boots. But then one trickled in, and then another, and then another. As it usually goes in high school, many were submitted right before the deadline.

Let us tell you: Reading through these essays was a joy, a privilege. Students wrote about pet lizards and college applications and climate change. They wrote about childhood trauma and Christine Blasey Ford; they wrote about their hopes, fears, grievances. The letters were a perfect encapsulation of what it means to enter a new decade: a snapshot of their lives now, and all they could be in the future.

We dreaded having to pick just one to feature as our winner. The essay below, though, particularly stuck with us. We couldn’t stop reading the last line. We kept turning the scenes over in our minds, drawing parallels to our own 16-year-old selves.

We’ve also included two other excellent essays that we consider runners-up.

To all the girls and young women who submitted: We want to thank you for letting us into your lives. In every essay, we found a kernel of self-awareness, of wonder, of wisdom. We can’t predict the future, but we suspect the next decade will be bright for all of you.

Dear imagined future self,

On Halloween, my best friend’s older brother sold us each one Poland Spring water bottle filled with watered-down vodka. There are now 15 dollars less to my name. We drank this vodka with a great deal of teenage bravado — trying not wince at the clear liquid’s resemblance to rubbing alcohol. My friend’s father made a crudité platter for us. The night ended with me throwing up baby carrots and mini peppers in my dad’s Honda, at the first hard left out of my friend’s driveway. Never have I felt more like a 16-year-old.

Future self, I hope you are more sophisticated now. Not a “blousy” adult who wears long necklaces — but the kind of adult who seems like they drink salads, wear camel coats and know the definition to words like “palaver.”

My dad didn’t say anything. I knew he understood what had happened, and why. Maybe the same thing had happened to him when he was 16. Silence hung between us like fog; I felt embarrassed to be alive.

He turned on NPR. Nina Feldman was reporting on memories. She said that our natural tendency is to misremember our experiences; we don’t understand what makes us happy, so we’re likelier to put ourselves into situations that actually make us unhappy. Her voice rolled on: For example, she said, there was a study in which people on vacation would write down how happy they were, on the hour. When they returned, they were asked to recall the happiest moments of their vacation. Almost no one’s memory of their happiest times lined up with what they actually experienced. It gets worse, she said. When people go to plan their next vacation, they unknowingly dedicate their time to things they thought they enjoyed, but actually hated.

This is not the kind of person I want to be. Future self: I hope you are not lying on a beach right now, surrounded by sand, shielding your lunch from a seagull. Beaches make you famously agitated. You hate them. Don’t forget it.

We pulled into the driveway. A thread of physical dread that had begun in my abdomen snaked up my back and was now strangling the space in my brain like an octopus capturing its prey. My shoulders buckled beneath the weight of life. I went inside without saying a word. I walked up the stairs slowly and carefully, like a pageant queen — as if I was fooling anyone. I changed, brushed my teeth and swished mouthwash around until the ethanol burned my gums. I had school the next day.

I used to go to a big, suburban public high school. The type you see in movies. My friends were mostly girls whom my mom couldn’t tell apart. We were like a wedding party with nothing but bridesmaids.

I moved to a new school this year. A Quaker school. The entire school feels as big as this room. But the ceilings are high — that’s what counts. The girls at the new school don’t like me very much. The boys do, but not in the way I want them to. I am changing and I am noticing, and the effect is that of waking up during surgery. For the first time in my life, I feel lonely. Loneliness is a funny thing in a world where the word “friend” means a click of a button that allows a stranger to see a set of images that are supposed to represent your life, and where a swipe right can land you dinner, a date and small talk.

On Wednesday afternoons, the entire school gathers for Meeting. We sit in silence on long wooden benches in concentric circles. Anyone can stand up and speak, if they feel moved to do so (by God, presumably). I measure how busy I am in a given week if I’m reviewing biology terms and planning out essays in my head instead of counting my breaths.

Students and teachers get up to say all kinds of things. Today, the girl next to me stood up. She told us about her friend from back home. He died at his own hands, with a handful of pills in his bedroom. “I’ll be okay,” she said. We held him in the light. Moments like these, I think you live through certain things before you understand them. You can’t always take the analytical position. The world is not an oyster that belongs to you, nor is it a ball of newspaper to be kicked around. I’m not sure what it is.

The girl sat back down and I offered her a mint I had in my backpack. She nodded. We each ate one. It felt refreshing; like prayer that dissolves under your tongue.

Dear Willow,

I had a brilliant idea for the opening of this letter — I was going to wax poetic about the tragedies of teenage life, the stresses of youth and all the things I’d enjoy writing but you’d hardly appreciate reading. But instead, after actually writing the address, I’m only wondering this: Do you still go by “Willow Taylor Chiang Yang”?

I don’t know if you remember, but our name was a core part of this identity that you’ve lived with for 27 years now. It was always a unique facet that was undeniable and immediate; if a stranger heard nothing else of us, at least they heard the strange name. And we all know how much we love being unique, being well-known.

If you’re reading this, that means you’ve lived to 27 years old; that’s an incredible feat in and of itself, if I’m any judge of our self-destructive tendencies. As someone still grappling with the ancient age of 17, I’m proud of you for lasting this far, for surviving past the 20s I’m anticipating will be stressful and terrifying beyond belief — was it as bad as I feared? Where did you end up going to college? Was it difficult? Was it as fun, as stressful, as liberating as so many say? And after that — what even comes after?

What of my current dreams of “after”? If you can remember, my biggest wish is to run for office and make even the smallest bit of idealistic difference in the bureaucratic government and corrupt world. Even writing this down now, I can imagine your self-effacing laugh, embarrassed derision curling at your lip as you recall the naïve ways of teenagehood. I can imagine your scoff, your weary and work-worn eyes even darker and more bagged than they are now, shaking a bitter head at this aged paper. What kind of deluded teen could believe in such a miracle?

Running for office, succeeding, being well-known — your eyes maybe close for a moment in some kind of nostalgic pain for long-gone, impossible enthusiasm. I’m sorry, if this is true; where did all the wishing and wondering and dreaming go? Can they be recaptured, or did they leave a hole of the unfillable sort?

But there’s another possibility, if we’re already drowning in hypotheticals, where it’s the opposite. I’m holding out for that reality, the one where a confident hand grips this paper with determination, where the eyes are vibrant and lively and alive, where each breath holds promise of fulfillment and excitement. One where, if not running for office, I’m doing something that stokes the excitement.

For the next 10 years, my every decision shapes every grain and pixel of your reality. Whether you’re successful, fulfilled, happy, good, weary, alive — whether your too-long name is known — all depends on the choices I make in the next, foggy expanse of a decade. I’m hoping for our sake that I make the right decisions; I suppose only you and the future know.

And if the former future — the one that seems a bit like death — is the one you’re living now, just know that you have another 10 years, too, if you choose to take it, and that I’m rooting for us.

Excitedly, nervously, naïvely you,

Willow Taylor Chiang Yang

Dear 2030 me,

I hope you know that I am proud of you. Wherever you are, whatever you are doing, or however you feel, you are still here. You are still standing, whether your legs feel strong and sturdy, or your knees are wobbling and your muscles are shaking and you are seconds away from collapsing. No matter how many times you hit the floor when you simply could not find the strength to stand, you rose each time, finding the worth in our heart even when our mind could not.

In the moments of life that allow you to embrace happiness, give yourself permission to relinquish yourself to that feeling. Welcome the warmth into your chest without trying to quarrel it with the coldness of the worry under your skin. I hope you are able to smile without questioning how genuine it is, and laugh without the weight of guilt pressing on your shoulders.

I want you to know that I do not know you. I only know the fragments of you that reside within me. I know that you have changed, and I am okay with the pieces you put back together. Acknowledge the growth that you have made, even if it meant leaving some parts behind.

I hope you remember the pain, but I also hope you have learned to love yourself without it. I hope you are allowing yourself to live the life you have been given. I understand that you are only 25, but do not use that as an excuse to undermine the life that you have lived simply because it is not the life you envision in your dreams. Trust that you are capable of creating that life.

I can only hope that you are allowing our heart to shine through over our head sometimes, it always did cower when our thoughts encompassed everything. Each thought became a needle that etched doubt and fear into our heart until they seeped into our blood and swam throughout the entirety of our body. Our body did not shake, it trembled. Our eyes did not cry, they poured. Our heart did not just bleed, it shattered.

Once I was done staring at the pieces in awe of my pain, I picked them up and got to work. I am putting myself back together.

I blamed our mind for so much, I blamed it for all the pain, all the anxiety, and I blamed it for breaking our heart. I want you to know that our mind is still beautiful, even if it hurts us sometimes; it is still learning to be okay with some things. Forgive it for what it has done.

I can imagine that there is still fear, that the anxiety still gets the better of you. Doubt does not have to hold you by the throat. Uncertainty means that you are in this world. Uncertainty allows for vulnerability to heal you.

Remember to return home when you need to, it is always there. Remember to feel the calmness of the ground beneath your feet when possible.

I hope that you have filled thousands of pages with the words that pump through your heart to your veins. Run your fingers over the words sometimes, you are a writer, make sure you feel that. Each word is a fragment of your soul. Each sentence is a piece of you that you bravely put into the world. Every phrase is vulnerable. Remember to read me from time to time. I am always in the pages, in the words. I am in it all.

Remember the girl before me, too. I know you long to get her back. Remember that she is still in our hearts, in our eyes. She will never leave us. She is a healthy reminder that we are allowed to smile, laugh, and be happy. She can remind us of the life that grows within us.

Life sprouts from the roots of your feet to the branches of your fingers. From the songs on your lips to the stars in your eyes and the flower of a heart that beats in your chest. The petals reaching and reaching into the sky, grasping everything they can reach. During the sunsets and sunrises they touch the horizon. At night, the galaxy of thoughts that expands in your mind is everlasting.

When you look out on the horizons of the earth and admire the immense beauty it radiates, you are getting a glimpse of the fabric of your being. The same beauty that writes the stars into the sky and the trees into the ground is within you. You are life, you embody it. Begin to love yourself the way you love the world.

I love you.

—You