Letter to Future self Collage

Why you should write a letter to your future self and how to start

Want to time travel? Try this.
March 18, 2024

I received something in the mail on the first day of the new year. And it frightened me. In fact, when I opened the small standard-size letter, and read the first line, “Hey there, future self”, I initially felt intense confusion. I read the dateline on the letterhead:

12/4/18

17 years old, senior year of high school

Realizing what the letter was, I shoved it back into the envelope. I felt uncomfortably emotional, and I couldn’t bring myself to open the envelope back up and read the letter that I had written to myself five years ago. I had forgotten all about it.

*Note: I deduced that the return address was that of my dual enrollment English teacher. Big thanks to her!

Handwriting
By Micah Boswell on Unsplash

The text fills up the whole page in single-spaced 11-point font. 17-year-old me had a lot to say to me today, and, frankly, I wasn’t sure if I wanted to know what it was. Mostly, I think I was afraid that I had not lived up to the 22-year-old version of myself that I anticipated I would be. I have always been a dreamer. The doing part? Not so much. My curiosity, normally so intense, did not immediately outweigh my fear of lack of accomplishment. I didn’t want to read about all the ways I had failed. Not yet.

The letter sat at the bottom of my book-bag for about two weeks before I read it in its entirety. I cringed; I laughed; I teared up (but mostly I cringed).

I had access to a strange perspective: a window in the shape of a letter allowing me to observe the intersection of two timelines and the evidence of a past life.

You should absolutely do this.

Here are some lessons that I learned

Progress doesn’t happen naturally. If you don’t actively try to change, you will end up in the same place.

Reading the letter, I realized that the last five years of my life had gone full circle, and I was back more or less where I started with the same goals and aspirations, but not much closer to achieving them.

There’s a quote I read from Elon Musk in his biography by Walter Isaacson that parallels this concept:

“People are mistaken when they think that technology just automatically improves. It does not improve. It only improves if a lot of people work very hard to make it better, and actually it will, I think, by itself degrade, actually.”
Elon Musk book cover by Walter IsaacsonElon Musk, Elon Musk
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Replace and refine some words and you’ve got an equally true quote:

People are mistaken when they think that they will automatically improve. You do not improve. You only improve if you work very hard to make yourself better, and actually you will, I think, without effort degrade.

Ouch.

A reminder of where you started can refocus your vision for the future.

So often we look into the past. As a visualization tactic, writing a letter to your future self can help you look into the future.

Visualization has been proven effective again and again. How powerful to have access to reverse visualization! It is like viewing the fork in the road: the you you are now versus that you you once imagined you could be. Reminding yourself of who you want to be, perhaps who you’ve always wanted to be, can be a great way to refocus that vision. It certainly was for me.

How to Write a Letter to Your Future Self

Having “writer’s block” might not be something you consider when starting a letter to your future self. However, the task can be daunting. Regardless, remember that you are the only person that needs to read this letter, and your future self will be grateful for the experience. Follow the steps below to get started.

1. Pick your medium.

There are sites like futureme that will send you a letter via email when the time comes, but I found the physical letter to be very impactful. If you’d prefer an experience like mine and don’t have a committed English teacher on speed dial, try Letter to Yourself. They will mail you a copy of the physical letter for a small fee up to 10 years later.

Otherwise, keep the letter somewhere where it will continue to be within the allotted timeframe (your home, the home of a friend or family member, etc) and set a reminder to retrieve the artifact.

2. Take a moment to reflect.

Use some of the prompts below to get you thinking.

The typewriter scene from "The Shining"

3. Try using a conversational tone.

Especially if you’re struggling to know what to write, just start by having a conversation. This makes the letter very impactful and intimate.

4. Find a safe place to keep your letter if applicable.

What to Write in a Letter to Your Future Self

1. Who are you now?

Describe yourself as you are. Mention things you want to keep doing, things you want to stop doing, and things you want to start doing.

2. What is going on in your life? What journey/project are you about to embark upon?

It is interesting to reflect on how you felt about an event in life before and after it occurs.

3. What are some life lessons you have learned?

This ensures you don’t unlearn them.

4. What are your predictions for the future?

Answer this. It is probably the most convicting and scary part. Especially if you don’t live up to your expectations when you reopen the letter, it can serve as a much-needed wake-up call.

5. What questions and hopes do you have for your future self?

Did you do that thing you’ve been wanting to do? I hope you did.

6. What is your current favorite song, Bible verse, movie or quote?

Art speaks to you differently at various points of life.

7. Bonus idea: Make this a partner exercise and write it with a loved one. You each write a letter to yourselves, and then you write a letter to each other’s future selves. I tried this below.

*Note: Something my letter included that I didn’t like was coded and ambiguous phrases. I wrote, “Whatever happened to June and July (you’ll get the reference … if it’s really you…)?” I guess it’s not really me because I have no idea what I’m talking about.

My Second Attempt

I wrote another one recently sent five more years in the future. While watching “I Origins,” my cousin and I distractedly hand-wrote notes–likely dramatized due to the content we were viewing–on crisp 3 1/2 by 5″ letters. Then, we proceeded to write a letter to each other’s future selves.

*Note: I do not recommend watching a thought-provoking movie while trying to write this.

**Note: Or maybe I do recommend it because everything thereafter felt like a scene from a movie.

I decided that we should bury our letters in the backyard of my childhood home.

I scoured my house for a suitable container. Then, while casting glances out the window at the streaking snow, we determined the standard box wouldn’t be enough to brave the rest of the Midwest winter–we needed something hardier. Something that could withstand five years buried under the ground in the continental climate of South Dakota.

I searched a couple of drawers in the laundry room before remembering the jar in the fridge filled with only an inch or two of pickle juice. Perfect.

A pickle jar
Photo by Kier in Sight Archives on Unsplash

I washed out the jar best I could, thinking that maybe the potent stench of vinegar and salt could be another part of the experience five years down the line. Maybe it would hit our noses when we cracked open the jar, freshly unearthed from the dirt, and bring back memories of what it was like to be 22 again (22 again and stupid as you will see).

We barely spoke to each other. We just looked at each other and laughed breathlessly like we were living on of those moments that would be imprinted in our minds forever as we stuffed the four letters, tucked into their envelopes, into the smelly pickle jar and readied ourselves for the cold.

Down jackets, woolen mittens, winter hats with tufty wool balls sitting on top (that serve no practical purpose?), phone torches, rusty shovels caked in summer dirt. We wore faces that said, “see you on the other side of this experience.”

That’s when the facade fell and reality took hold.

Cold air hit our exposed skin in a fury of wind and snow.

The thought hit me, like I hadn’t allowed it to before, that it might be too cold to dig. Then I remembered the show I had just finished watching with my mother, “Black Bird“, about the serial killer Larry Hall who grew up digging graves for his father in all sorts of weather. He had been depicted as a flabby and stubby youngster (I recently discovered that the word for this is fubsy). I had more muscle than that kid.

*Note: if you’re into adapted true crime shows, this is a good one. Taron Egerton is stellar and highly charming as Jimmy Keene.

So never mind that it was below freezing, snowing, and starless dark outside. This was going to work. It had to–we were main characters, gosh darn it!

We found as good a spot as any covered in about a half-inch of powdery snow. I positioned the blade of the shovel on the ground, brought my foot to the step, and heaved. Nothing. I corrected my stance and tried again. Nothing. My cousin tried, leveraging her angle better, and the shovel submerged in the earth … about a centimeter. A minuscule dent. We tried for five minutes fruitlessly attacking the ground (or I did while my cousin laughed at me from the sidelines), but it had been clear from the get-go that this wouldn’t work. In the end, our work yielded only some misplaced snow and a flake of dead-grass-tufted dirt.

I read a few days later in Kristin Hannah’s The Winter Garden about a burial that couldn’t happen in Leningrad, Russia due to the frozen ground. The characters in the book were smart enough to not even try to dig and they were half-starved and out of their minds. This made me feel a little silly. Of course you can’t dig a hole from frozen ground. Even the the miniseries depiction of fubsy and juvenile Larry Hall only dug in, at worst, the rain.

With the magical quality of the scene gone, we decided to put a pin on the burial process of the letters until the Spring. The summer at the latest. For now, the jar rests in a bin in the mudroom of my parent’s house.

Key Takeaway

Write a letter to your future self. This is as close as anyone can get to time travel. Yes, we have pictures and videos, but neither of these equates to reading the mind of a you that no longer exists.

Thea

Currently has 44 tabs opened on four different windows, 808 unread text messages and 77,734 unread emails (on a spam account if that makes it better). That is what she means when she says she likes to “disconnect” from the internet--she ignores the world!! She has moved five times in the last five years.
Chaotic energy aside, she has positive traits, however, they are not listed here.

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  • Thea

    Currently has 44 tabs opened on four different windows, 808 unread text messages and 77,734 unread emails (on a spam account if that makes it better). That is what she means when she says she likes to “disconnect” from the internet--she ignores the world!! She has moved five times in the last five years. Chaotic energy aside, she has positive traits, however, they are not listed here.

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