Writing a letter to your future self may seem like a dorky thing to do, but if you do it right it the results can be super cool.
Pretty Cool Stuff
On my first day of high school, our guidance counselor had our class write letters to our 12th grade graduating future selves.
Some of my classmates were too cool to put any effort into it. I was dorky enough to write a four-page letter. I filled it with YA-novel-worthy predictions/goals/dreams about how many girls I’d kiss and date, who I’d be friends with, and what university I’d be heading to.
Five years later, my classmates and I morphed into the future selves we’d written to. We reassembled in the same room as Day 1. And the counselor returned our letters.
The cool kids who hadn’t bothered had nothing to look forward to. I was giddy with nostalgia, anticipation, and appreciation to my pre-teen self for making the effort.
What a gift!
And what a surprise.
The letter’s contents were way different from what I remembered. My predictions were even more hilariously misguided than I recalled. And I could hardly believe I’d written some of the things in it.
I learned a lot from reading my letter to my future self:
- How much life turns out different from expectations.
- How much you turn out differently from expectations.
- How unreliable memories are.
- How fast time flies in retrospect.
Most importantly, I learned the value of doing favors for my future self. It’s a lesson I’ve applied ever since. My younger selves have generously given me a healthy body and mind, ample savings, fond memories, a great wife, close friends and family, and the best job ever. Pretty cool.
But I stopped writing letters.
Today, I’m writing a second letter to my future self.
I don’t care if other people think it’s uncool. I’m still a dork. And I’m putting a ton of thought into the letter because I want my future self to be extra thankful for it.
Here’s my plan.
How to Write a Life-Improving Letter to Your Future Self
Step 1: Come Up With a Good Purpose
Why are you writing a letter to your future self?
Another lesson I learned more recently is that the more mental effort you put into clarifying the purpose of any activity you take on, the higher the returns you get out of it.
Dinner parties with friends are more memorable. Meetings are less of a waste of time. Workouts are more motivated. Time is more wisely spent. I’ve even attempted to clarify the purpose of my life with my personal mission statement.
So what’s the purpose of writing a letter to my future self?
Or, maybe the better way to put it: How will I know if the exercise has been a success?
Here’s my answer:
My letter to my future self will be a success if, when I read it a year from now, I am grateful I did it and want to pass on the favor by writing another one the next year.
That would mean the exercise will have:
- Reinforced my patience, long-term thinking, and intentionality.
- Made me happy (or feeling some other emotion) when I read it.
- Taught me lessons about myself or my psychology that I can learn from and share on this blog.
Pick whatever purpose you want for your letter to your future self. Don’t be lazy and skip this step. It’s worth the effort.
Step 2: Set Realistic Expectations
Look back before you look forward
Don’t expect to magically “cure” your fatness and get back to your ideal weight this year if you’ve been putting on five pounds a year for the past decade.
And don’t expect to be married to the love of your life by the end of the coming one if you haven’t convinced anyone to go on a second date with you for years.
Such over-ambitious expectations do nothing but discourage you when you inevitably fail to live up to them.
So be more realistic than optimistic with your letter to your future self.
The best reality check?
Think back on how much you changed in the previous year. That’s a good baseline for how much you can likely change in the next.
For me, that’s easy. I plan, review, and recap each month as part of my lifelogging practice. So for my letter to my future self, I’ll go through and summarize those into three big buckets:
- Social (friends, family, love life)
- Personal (personal development, physical health, mental health, finances)
- Work (jobs, side-hustles, contribution to society)
Then, based on how much progress I’ve made in each over the past year, I’ll plan and predict what I can accomplish in the year to come.
Let’s look at my job for an example.
My “job” is this blog. At the beginning of this year, I thought I’d have 250,000 monthly visitors and 10,000 subscribers to the blog by now. Nope. I’m closer to 150,000 and 3,000.
But it wasn’t a disappointing year by any stretch. I had no idea how much I’d shift from travel-related content to personal development. And I didn’t imagine how much this would help my own personal development. So even though the blog hasn’t had the success in audience growth I expected, I’ve gotten more from it than I had hoped.
Knowing this both tempers my hopes and widens my horizons for the coming year.
Step 3: Start With Today
Don’t make your letter to your future self all about the future
In 1962, psychiatrist Daniel Offer asked 73 14-year-olds questions about their parents, home, friends, and school. Thirty-four years later, he found 67 of them and asked them to remember what they had said.
The adult’s confident answers were no better than wild guesses. They’d forgotten what their favorite pastimes were, how much they disliked homework, and what they thought of their parents.1Read one of the books that changed my thinking, Mistakes Were Made But Not By Me, for more on our astonishingly unreliable brains.
What does this have to do with writing a letter to your future self?
It goes to show that your “memories” are often lies your brain tells you to keep you happy. That’s why it’s a good idea to start your letter to your future self with what’s going on in your life today.
- Where are you as you write the letter?
- What has you worried?
- What are you excited about?
- What’s going on in your life and the world at large?
Add details like the color of the coffee cup you’re drinking from or the dinner party you went to yesterday. They will rekindle more accurate memories.
Be honest. The more honest, the better. Not only will it feel cathartic to do today, but your future self will also appreciate it. It will help them remember just how much you’ve changed over the past year.
And be grateful. Write about what you have today that you may not have a year from now.
Step 4: Make Predictions (Not Goals)
Set your direction, not your destination
Now the fun part of writing a letter to your future self: guessing what will happen between now and the time you read it.
Start by thinking of your goals. Tie them to your purpose, be realistic, and touch on all aspects of your life—social, personal, and work.
Then disguise your goals as predictions.
That way, you set a direction without being dead-set on a destination. If circumstances change, you won’t feel obliged to fight the current to not fail at achieving your goals. You can accept that your predictions sucked and adjust course to make the best of your situation.
Here are some prediction ideas to stimulate your creativity:
- Where do you think your future self will be reading the letter? How will you be feeling as you open it?
- What will have been your proudest accomplishments?
- What will be the fondest memories you’ll have created?
- How will you be different from who you are today?
- Social: How many times will you see your family and close friends this year? How many people will you date?
- Personal: What will be your weight, maximum bench press, or investment portfolio value? How many books will you have read?
- Work: What will your salary be? How many people will be subscribed to your newsletter or following your social media accounts? How many direct reports or employees will you have?
Wild Card Predictions
Make predictions you have no control over but are just for fun and to test your crystal ball reading ability:
- Who will have won the NBA championship?
- Which stocks will have gone boom or bust?
- What will be the hot topics in the news?
- What or who is going to be more/less popular?
Step 5: Begin a Conversation
Ask your future self for their wisdom on important questions
Brainstorm with your future self to take advantage of their additional wisdom, extra life experience, and different perspective.
For example, I can share my answers to my 10 “GPS” questions and ask my future self what he thinks. One of those questions is, What is your definition of “winning at life”? Is his definition still the same as mine, or has it changed? If so, why?
I can also ask my future self’s opinion on doubts I have:
- Is Kim and my choice to live between Vancouver and Cape Town sustainable and healthy for us and any kids we have?
- Should I keep plugging away at YouTube or reallocate that time to my blog? Or should I try something new like courses or a podcast?
- What skills should I focus on developing to make the most of my potential? Should I hire someone to help me develop them?
Two minds are better than one. You can even make it three by having your future self ask their future self the following year.
Future Self Relationship Therapy
The science behind why most of us have poor relationships with our future selves and what to do to improve them.
Step 6: Send Your Letter
If you don’t trust yourself not to sneak a peek during the year, try using FutureMe.org. It’s free. Or you could email it to a friend, delete it from your Sent Emails folder, and set a reminder to ask them to send it back next year.
But the best way to send your future self a letter is probably an old-fashioned, handwritten letter. Seeing your handwriting makes it more personal, especially if you continue the practice for many years. Insure against the risk of losing the letter by snapping a picture of it and using one of the email techniques as a backup. Write the date you wrote the letter and the date to read it on the front of an envelope, put the letter in, and seal it. Maybe put a nice bottle of wine with it as a gift for your future self, too.
What Are You Waiting For?
If you’re on the fence about writing a letter to your future self, ask yourself this:
How would you feel if you got a letter from your past self today?
You’d be excited to read it and grateful to your past self for putting in the effort, right? If so, what’s your excuse for not writing a letter to your future self?
Don’t be selfish. Set some direction and purpose for the year to come. Then make it happen. Give your future self something to look forward to.
Keep Doing Favors for Your Future Self
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