5 Reasons to Write a Letter to Yourself (and How to Do It)

In high school, my English teacher had everyone bring in a self addressed envelope. She gave us some paper and told us to write a letter to our future selves. I didn’t appreciate it at the time, but I realize now that she was doing us all huge favor. She was giving a gift to our future selves.

After we wrote the letters, she took them and said she would mail them in five years, just as most of us would be graduating from college.

I will never forget reading that letter when it came back to me, exactly five years later as she had promised. It was a rare chance to reflect honestly on the passage of time and on my own personal growth over that formative period in my life.

This is an incredible exercise to do no matter how old you are. Writing a letter to yourself gives you insight and teaches you valuable life lessons that will stick with you long afterwards. Think of it as a time capsule.

1) Cultivate gratitude.

One of the best things for your emotional health is to practice gratitude regularly. It reduces stress and helps you realize what you have. If you’re going to write a letter to yourself, an expression of gratitude is one of the wisest things you can include.

This letter is a message in a bottle. When you open it years from now, you likely have forgotten what you wrote. So give yourself a gift relive some of the same thoughts that you feel today..

Fill it will positive affirmations and appreciation for the person you are. When it’s time to open it up, your future self will thank you.

2) Increase self-awareness.

Do you ever go back and scroll through your old Facebook posts? It hurts, doesn’t it? Like listening to a recording of your own voice.

It’s uncomfortable, it’s a healthy discomfort, because you’re confronting your own shortcomings. You’re embarrassed by your own naivety and your lack of self-awareness. This is actually a good thing, because it shows you how much you’ve grown.

When I opened my own letter after five years, I was blown away by two things– how much I had changed, and how little I had changed. It’s incredible how we can grow and shape who we are, but we are still fundamentally and unalterably ourselves.

All of your quirks and thought patterns will show up as plain as day. You take one step closer toward understanding exactly what is is that makes you authentically YOU.

3) Create your future.

Where will you be in five years? Who do you want to become?

Maybe you’re stuck in a dead-end job, or you just graduated and you’re uncertain about your future. It can start to feel like your best days are behind you.

This exercise helps get your thoughts out of the present and keeps you focused on what is yet to come. Sit down and address a letter to yourself in 3, 5, or 10 years and tell me that you don’t feel hopeful and excited for your future.

Let your mind run wild. Think big and give yourself permission to be wildly ambitious. What principles will guide your life? What do you hope to accomplish? How are you going to do it? If you vividly imagine your future in concrete terms, it becomes a self-fulfilling prophecy.

4) Appreciate the passage of time.

One day, your life is going to end. This is hardly a revelation, but it’s human nature to avoid thinking about it. We can be so consumed with our demanding jobs and fast-paced lives that we fail to see the bigger picture.

Rather than think day-to-day, we can gain so much if we challenge ourselves to comprehend years and even decades. Experiencing life this way brings patience and confidence to every action. I challenge you to try to think farther ahead. Sending a message to yourself forces you to do this.

It’s contradictory, but this also brings urgency to every action. When the thought of death and getting older are present, it becomes easier to realize the shortness of life. You have to hurry to get the most out of it.

5) Give yourself a memory.

Are you about to go to college? Getting married? Moving to a new city? If you’re starting out on a brand new journey, there is no better way to commemorate it than by writing a letter to yourself. Like a snapshot of your life at a point in time, it will be nostalgic to look back and see what you were thinking at this pivotal moment in your life. Were you worried about something stressful that turned out to be no big deal? Or maybe you regrettably forgot to stop and smell the roses?

You could even make this an annual tradition– write a letter to yourself every year, but don’t open it for another five years. This way, once the first letter “matures” in 5 years, you have a constant stream to read and to cherish every year for the rest of your life.

How to Do It

One simple resource is FutureMe.org (futureme.org). This site lets you send an email to yourself and have it delivered at a future date.

For a seamless experience that is a little more hands-off, try Five Year Letter (fiveyearletter.com). When you sign up, you will receive a real physical letter in the mail that guides you through the process. Then you mail it back in the prepaid envelope and wait.

Of course, you could do it yourself, as long as you remember to open it– and you have to resist the temptation to open it too soon. Don’t forget to date it!

What To Write About

  • Give advice. Use the second person to make it more personal and direct.
  • What are your professional goals? Your romantic ones? Intellectual? Financial? Spiritual? Personal? The more specific you are, the more likely you are to see improvements.
  • What causes you the most anxiety about your future? What keeps you up at night?
  • What have you done wrong? What is your biggest regret?
  • What are you excited for? What does your ideal life look like?
  • What was your favorite book this year? How did it affect you?
  • Who are the 5 most important people in your life, and why?

This is just a starting point. The important part is to just be sincere and thoughtful. Write your letter, send it off, and then forget all about it so that it can surprise you later. Your future self will thank you.

Until then, go live your life! It is only what you make it.

Scott Hughes is a writer and entrepreneur in Philadelphia. His project, Five Year Letter (fiveyearletter.com), helps people write letters to their future selves so they can get the most out of life. Email him at scotthughes.us@gmail.com.


Erin shows overscheduled, overwhelmed women how to do less so that they can achieve more. Traditional productivity books—written by men—barely touch the tangle of cultural pressures that women feel when facing down a to-do list. How to Get Sh*t Done will teach you how to zero in on the three areas of your life where you want to excel, and then it will show you how to off-load, outsource, or just stop giving a damn about the rest.

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