Worth Another Shot?
On my first day of high school, our guidance counselor had our class write letters to our 12th grade graduating future selves.
Most 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 metamorphosed 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 had nothing much 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.
My predictions were even more hilariously misguided than I recalled, and I could hardly believe I’d written some of the things I read.
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.
Ever since, I’ve tried to apply that lesson by working to give my future self a healthy body and mind, ample savings, fond memories, and close friends and family.
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 my letter because I want my future self to be extra thankful for it.
Here’s my 6-step plan.
Step 1: Come up with a good reason to do it.
Here’s another lesson I learned more recently:
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.
So what’s the purpose of writing a letter to your future self?
Or, maybe the better way to put it is this:
How will you 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 Future Me wants to pass on the favor by writing another one the following year.
That would mean the exercise will have:
- Made me happy (or feeling some other emotion) when I read it.
- Reinforced my patience, long-term thinking, and intentionality.
- Taught me lessons about myself or my psychology that I can learn from and share on this blog.
Step 2: Don’t forget the present.
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 tested how accurately they could remember what they had said.
They failed miserably.
Though confident in their answers, the adult’s accuracy in recalling what their 14-year-old selves once thought was 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.
What does this have to do with writing a letter to your future self?
It goes to show that “memories” are often lies our brains tell us to keep us happy.
That’s why it’s a good idea to start your letter to your future self with what’s going on in your current self’s life.
- Where are you as you write the letter?
- What are your worries, frustrations, and insecurities?
- 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 3:Look back before you look forward.
Try to set realistic expectations for what you might accomplish between the time you write your letter and when you read it.
- 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.
- 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 almost certainly fail to live up to them.
How do you be more realistic than optimistic in your letter to your future self?
If you, like me, are writing a letter to yourself to read a year from now, ask, How much have I changed in the previous year? That’s a good baseline for how much you can realistically hope to change in the coming year.
Since I plan, review, and recap each month as part of my lifelogging practice, I have a very good idea of how my life’s changed. For my letter to my future self, I’m summarizing those changes 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.
To give you an example, let’s look at my job—my “job”—this blog:
At the beginning of this year, I thought that by now I’d have 250,000 monthly visitors and 10,000 subscribers. Nope. I’m closer to 150,000 and 3,000.
Maybe I’m self-justifying, 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 audience growth I hoped for over the past year, I’ve gotten a lot from it—just in a different way than I expected.
Knowing this both tempers my hopes and widens my horizons for the coming year.
Step 4: Make predictions.
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 realistic goals for all aspects of your life—social, personal, and work.
Then disguise your goals as predictions.
This 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, adjust course, and make the best of your new situation.
To stimulate your creativity, here are some prediction ideas:
- 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: Brainstorm.
Ask your future self the questions you’re struggling with to take advantage of their additional wisdom, life experience, and perspective.
For example, I will ask my future self:
- 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?
If Future You remains uncertain, they can always bring in a third perspective asking their future self the following year.
Step 6: Send your letter.
Maybe the easiest and most private approach is to write yourself an email then snooze it so it returns to your inbox a year from now. (Here’s how to do so with Gmail.)
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 in your calendar to ask them to send it back.
But probably the best way to send your future self a letter?
An old-fashioned, handwritten letter.
This is the approach I’m taking. I feel that seeing my handwriting will make it more personal, especially if I continue the practice for many years.
If you too go this old-school route, consider the following:
- 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.
As far as I could figure out, there is no way to physically mail yourself the letter to have it return to you at a predetermined date in the future, so I’ve hidden it away in my suitcase so it will be with me wherever I end up.
Recap for future reference:
How to Write a Letter to Your Future Self
What Are You (and Future 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 good excuse do you have for not writing a letter to your future self?
Be a selfless friend to Future You. Set some direction and purpose for the year to come. And have fun with it.
Then go give your future self something to proudly look back upon.
Update: It’s been a year since I wrote my letter to my future self and the results are in! Read how the experiment worked (and didn’t work) for me:
↳ The Benefits and Lessons of Writing a Letter to Your Future Self.
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About the author
I'm Chris. Grinding for conventional super success was exhausting, so I zagged. Now, my life's getting better and better—and part of that involves pushing you to work toward the same.
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