The (Un-)Expected Benefits of Writing Letters to Your Future Self

This New Year, I got both a generous gift and a face-slap reality-check from one of my favorite people in the world:

Myself!

The gift came in the form of a letter I wrote on Dec 30, 2020 for my future self to read a year later.

Back when I wrote it, I also came up with five potential benefits of writing letters to your future self. And, to justify the super self-involved exercise, I proposed those benefits to my newsletter subscribers:

1. A gift I would look forward to opening.
2. A pleasant dose of nostalgia.
3. A better appreciation for how time flies.
4. A lesson on how much I suck at predicting the future.
5. A general sense of direction.

Now, 376 days later, it’s time to assess whether or not those benefits panned out.

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The Expected Benefits of Writing a Letter to My Future Self

1. Did I appreciate the gift of this letter from my past self?

I haven’t looked forward to opening a gift this much since I was a kid.

Verdict: ✅ Easy win.

2. Was it a pleasant dose of nostalgia?

The first part of my letter to my future self was about what was going on in my life and what I was feeling at the time I wrote it.

It felt like a mini time trip back to where I wrote it, the Orange River between Namibia and South Africa, and into the mind of my younger, more optimistic, less-wise, and child-less self.

What made it extra impactful was that I had forgotten about many of the details in my letter. This taught me the bonus lesson on how unreliable my memory is and on the value of preserving little anecdotes that rekindle fading memories.

Verdict: ✅ A hard-to-forget success!

↳ Note: The fact that I hand wrote the letter made it feel extra intimate.

3. Did it give me a better appreciation for how time flies?

Reading my letter to my future (now current) self and reflecting on the year that had come and gone felt like looking at the bottom of a Dairy Queen blizzard cup:

• I wished there was more.
• I wished it hadn’t disappeared so quickly.
• I wished I could go back and do it again.
• And I vowed to take it slower next time (which won’t happen).

Verdict: ✅ Bittersweet victory.

4. Did I learn a lesson on how much I suck at predicting the future?

This was part of why I called my letter to my future self a face-slap wake-up call in the intro.

My missed predictions on topics I had no influence over—NBA champions, stock performance, global issues—were funny. Maybe I’ll read Superforecasting next year. [Update: Done! But I doubt it’ll help me.]

My missed predictions on things more under my control stung. For example, I failed to reach even half of the income, subscriber, and reader numbers I predicted for this blog. Maybe I need to temper my optimism? Or do better…

Verdict: ✅ Humbling-ly accurate.

5. Did it give me a general sense of direction?

Since I accomplished less than I had hoped in 2021, it seems the exercise of writing a letter to my future self either set the wrong direction or didn’t motivate me enough.

On the bright side, it has motivated me to learn from my mistakes to do better in 2022.

Verdict: ❌ Failure this year, but maybe I can turn it into a success for the year to come?

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The Unexpected Benefits

✅ A Swift Kick in the Pants

Before I read my letter, I thought I had some new ideas in mind for what to pursue next year, such as:

• Focus on 1st-person storytelling.
• Finding mentorship/coaching/masterminds for the blog.
• Organizing a camping trip with family/friends in Canada.

But it turns out I wrote those exact same ideas last year!

Somehow, I’d completely forgotten about them. So the fact that I’m again thinking about doing them tells me not to put them off any longer.

✅ Perspective on How Much I’d Grown

In my letter, I recapped my favorite personal developments from 2020. That was heartening to be reminded of. It also got me thinking back on how I’d developed 2021.

This perspective encouraged me!

While I didn’t reach all the metrics I’d hoped for in the past year, I’d still managed to make praiseworthy progress up my life’s “y-axis”: Growth.

✅ A Desire for More

The letter I wrote last year was an experiment. I wasn’t sure how it’d work out, but:

1. The investment was minimal, and
2. It gave me something to blog about.

Now that the results are in, I can say this:

My experiment was a success!

So last week, I transformed the experiment into a tradition by writing a letter to my 2022 self.

And I learned my lessons (I hope). This time, I plan to do a better job making the plans, goals, and predictions I write in my letter a reality.

That way, when I read the letter a year from now, hopefully it’ll feel less like a slap-in-the-face wake-up call and more like a rewarding fist bump.

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Would You Consider Writing a Letter to Your Future Self?

If so, you may be interested to check out an example of the letter to my future self I wrote this year based on these lessons I learned, a 6-step how-to guide, and some additional tips.

If you’re not convinced about writing your future self a letter, what’s holding you back?

And if you’ve done so before, what was your experience? Did you experience similar benefits, or something different? Write a brief letter (AKA comment) to my current self below.