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Where will you be in 5 Years?


“Dear Future Me”

When I was in high school, I had a teacher who asked us to bring in a self-addressed, stamped envelope. She told us to write a letter to ourselves by hand. She was going to hang on to it and mail it in exactly five years, just as most of us would be graduating from college.

I did my homework, wrote the letter, and promptly forgot all about it.

But I will never forget how I felt when I received that letter five years later. When I saw the envelope, I knew instantly what it was, but I put off reading it for nearly a week because I was so anxious. It sat on my shelf, taunting me. Threatening to embarrass me with my 18-year-old ambitions and half-baked opinions.

Do you ever scroll back through your old Facebook posts from 4-5 years ago? Hurts, doesn’t it?

In his book “Sum”, writer David Eagleman imagines that we die two deaths: the first is physical. The second death comes later, as the surprise we feel when we see ourselves the way others see us. When we see ourselves as we really are.

My letter hurt like that. It was a punch in the gut because it showed me how I used to be– that awkward and naive teenager who I’d worked so hard to help grow into a better man.

But it was also immensely empowering for the same reason. It showed me how far I’d come and how much I’d changed. It was a time capsule, a window into my own successes and evolution as a human.

It reminded me of my values and helped me identify ones that I’d outgrown. It made me think of old friends and girlfriends. It rekindled my love for art and music and books that I had loved.

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And in some ways, my letter showed me how little I’d changed. How I had failed to grow and learn from my mistakes. How I was still wrestling with so many of the same problems.

At that moment, this letter changed my life and affected how I behaved going forward.

Why to Do It

I think everyone should try this. Writing a letter to yourself can be a profound experience. You’re literally communicating with a future version of yourself.

It’s hardly a new idea. Think of Marcus Aurelius’ Meditations, or Montaigne’s Essays — both designed to help them think through their problems and remind themselves what is important.

Writing to yourself is a form of positive self-dialogue where you give yourself permission to imagine your own successes in vivid detail. And it’s an opportunity to confront the tough questions:

Where do you want to be in five years?

What advice do you have for yourself?

What are your greatest fears?

What do you hope to never forget?

Writing a letter to yourself is better than a journal, because you will be forced to check in in five years.

Use this tool to guide yourself and define how you want your future to unfold. And when the time is up, you can’t avoid it– you have to open it up and basically answer to yourself. Was it a great five years? Or did you let yourself down and fail to meet expectations?

Do it by hand. Trust me on this. There’s something magical about the written word that doesn’t happen when you type. When you actually put pen to paper, you tend to go slower and you spend more energy. For this project, that is a good thing. You have to be more deliberate because you can’t hit backspace.

How to Do It

You have two options:

  1. Do it yourself. Just write a letter, pick a date. and don’t forget about it. Set a reminder in your calendar app. Stick it in your basement check back with yourself later.
  1. Five Year Letter (fiveyearletter.com). Sign up online and they send you a template with a return envelope. Once you finish you letter, just mail it to back and it will be returned unopened when the time is up.

The older you get, the faster time seems to move. Are you seize the day and take stock of where you are? Will you commit to being better?

Or are you going to let it keep passing by?

Title photo credit: flickr

in your inbox everyday at 10am CST.

No fluff or "pie in the sky inspiration." Just real stories.

Written by Scott Hughes

Scott is from Philadelphia, PA