Extensive Tips for Writing Impactful Letters to Your Future Self

Based on my experience, writing a letter to your future self is a high leverage activity.

With only a little effort, it can be quite moving. So it’s tempting to be lazy:

• Write a quick stream of consciousness letter.
• Hide it away.
• Fast forward to the future.
• Pull out your letter.
• Read it and be like, “Haha. Cool.”
• Move on to the next easy self-help exercise.

But, like with any lever, if you put extended thought and effort into a letter to your future self, it’s exponentially more powerful.

That’s why I filtered the internet for the best tips, ideas, and prompts I could find and compiled them into these future self letter tips.

There’s a lot in this guide. Maybe too much. But hopefully it’ll help myself and anyone willing to go beyond half-assed effort and top-of-mind clichés leverage our letters to our future selves to their maximum potential.

Why write a letter to your future self?

• A gift to future you. Imagine sifting through an old box of your crap and finding a letter you forgot you wrote yourself. Wouldn’t you be super excited to read it? Well, do your future self that favor. (But don’t forget about it.)
• Improved strategy. If you want to perform well in the game of life, it makes sense to take periodic time-outs to figure out your next plays.
• Better memory. You won’t believe how unreliable your memory is, and how much you change over time, until you see it in your own words.
• More appreciation for time. We all know time is precious, but a letter from your past self makes you feel it.
• Crystal ball reading practice. It’s fun, humbling, and informative to see how inaccurate you are at predicting the future.
• A reality check. Comparing what you thought you’d accomplish to what you actually get done gives you a more accurate idea of what you’re capable of in a given period.
• Kick in the pants. The difference between what you had hoped to accomplish and what you really got done can motivate you to pick it up.

For more, see The Benefits and Lessons of Writing a Letter to Your Future Self.

What should you write about?

Try to include all five of these components

1. The Present
   • Where are you writing the letter?
   • What have you been watching/reading/doing recently?
   • What are you worried or excited about?
   • What are your current short- and long-term priorities?
   • What relationships are you enjoying or struggling with?
   • What have you recently accomplished/failed at?
   • What’s going on in the world at large?
2. The Past
   • What are your proudest personal developments from the past period?
   • How have you been doing financially?
   • What progress have you made in your career?
   • Who have you gotten to know or lost touch with?
3. The Future
   • Where do you expect to be when you read the letter?
   • In what ways will you be different from today?
   • Where do you hope to travel?
   • What bucket list items do you expect to tick off?
   • What habits do you wish to have developed/broken?
4. Questions (See the next Q&A.)
5. Advice
   • What final message do you hope your future self keeps in mind?
   • More on this below under how to finish your letter.

What questions should you ask your future self?

Ask questions that your current self is grappling with and you could use Future You’s help to tag-team. For example:

• Where should I live?
• Who do I want to spend my time with—romantic partners, kids, friends, family?
• What should I be doing less/more of?

And ask “GPS” questions—i.e., those that help guide your future self down the right path.

• How do you measure success in life?
• What do you want your great-great-grandchildren to remember you for?
• What problem do you solve?
• How do you define “winning at life”?
• If you had $100 million, what would you do differently with your life?
• What’s your purpose and how are you working toward it in your job and personal life?

Can you suggest some prompts for my letter to my future self?

To get the ball(-point pen) rolling, consider these questions:

• What do you hope to get out of writing and reading this letter?
• What do you never want to forget?
• Where are you worried you may go astray?
• What are you doing today that you
• What are some things you hope to try one day?
• What pep talk would you give your future self if they’re feeling down?
• What advice would you give your younger self?
• What’s your philosophy toward life?

How do you start a letter to your future self?

Write the date you’re writing your letter on the top, Dear Future [Your Name] below that, then begin with detail on what’s going on in your life today.

It may seem boringly obvious to you now to be writing about where you are, what you’ve been up to, what you’re working on, and what you’re worrying about. But believe me when I say your future self will appreciate hearing all the details about your life—just like your grandma does.

Vivid detail provides a healthy dose of nostalgia. It also allows Future You to time travel back, re-sharpen fuzzy memories, and repair distorted ones.

How do you finish a letter to your future self?

Use the peak-end rule to your advantage.

We tend to remember events (or letters) and judge experiences based on their biggest highlights and how they end.

Therefore, end with:

• The most important message you can think of transmitting to Future You.
• Positive vibes.

How far in the future should you write to?

In many ways, the longer into the future you write, the more meaningful it will be for your future self to read. For instance, I’m 36 now and would prefer to read a letter from 18-year-old me than my 35-year-old self.

But, sorry to sound like Captain Obvious, the further into the future you write, the longer you have to wait. And that means it’ll be longer until you can reap the benefits and lessons of this future self letter exercise and decide whether to do it again.

So if this will be your first letter to your future self, shorten your time horizon. Or, if you’re gung-ho, write two letters: one to your future self six months or a year from now, and another for five, ten, or more years into the future.

How long should my letter to my future self be?

The more comprehensive your letter, the more you’ll get out of the exercise.

To give you an idea, my letters end up being around 3,000 to 4,000 words long.

But if that seems overwhelming to you, start small. Target just a few hundred words—about one page. Better to have something than nothing. Anyway, once you get momentum writing your letter, you may find it hard to stop.

How do you send an email to your future self?

If you typed your letter:

Easy. Use FutureMe.org or send yourself the file via Gmail and snooze it until the date you want it to return to your inbox.

If you handwrote the letter:

As far as I know, there is no mailing service that will deliberately take months or years to send. You’re probably best off putting it in an envelope with the date you want to open it written on the front, hiding the letter away somewhere safe, then setting a reminder in your calendar for the date you want to read it.

To be extra safe, photograph or scan the letter, then upload this backup on the cloud or to your email.

Is it better to handwrite the letter?

Yes.

First, it gets you away from your computer so you’re less distracted and freer to unspool your thoughts.

Second, it’s more personal. Just like a distant grandparent, your future self will appreciate the touch. (On this note, as per one of the studies I refer to in my guide to befriending your future self, framing the actions you take as your social responsibility for caring for your older future self will motivate you to make better decisions.)

Third, it creates an artifact from the past. Minimalists may disagree, but you may value a collection of physical, handwritten letters from your past selves more than a virtual folder of emails.

Can I see an example of a letter to your future self?

Here you go: Example Letter to Your Future Self (With Outline Suggestions)

And for more detailed tips on structuring your letter, check out How to Write a Letter to Your Future Self.