The Curiosity Chronicle
The Curiosity Chronicle
Letter to Your Future Self

Letter to Your Future Self

An annual tradition with a 10x unlock for your life

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Today at a Glance:

  • The letter to your future self is a 10x unlock for life. The process of writing a letter forces deep reflection on the present and thoughtful rumination on the future.

  • Use a baseline time horizon of 5 years in the future, but adjust as you see fit. A basic letter structure to follow: (1) Reflections on the Present, (2) Changes to Make, (3) Goals for the Future, and (4) Fun & Crazy Predictions.

  • I handwrite the letters and store them in a cabinet, but if you’re looking for a more technology-enabled solution, there are tools like FutureMe that should do the trick.

Letter to Your Future Self

I’m always on the lookout for the “10x” opportunities in life.

What does that “10x” mean?

These are the step-function improvement or growth opportunities.

My generalized mental model for life is that truly meaningful change is only felt in 10x increments. This is a *very rough* approximation based on my own experiences. I think too many people jump at every 2x opportunity they encounter in life and thus find themselves too busy or without the mental bandwidth to capitalize on the 10x opportunities when they arise.

To be sure, you can achieve these 10x improvements through slow, steady, daily compounding of small gains—through consistent small wins. But now and then, you can achieve them through a single practice or tool, applied with deliberate focus and intention.

I’ve shared a few of the 10x practices I’ve uncovered in the past:

In today’s piece, I’d like to share another: the letter to your future self.

Let’s dive right in…


Every year on my birthday, I write a letter to my future self.

The idea of writing a letter to your future self certainly isn't new. In fact, the first time I did it was in middle school. A few days before my 8th grade graduation in June 2005, our entire class was required to write a letter to ourselves that would be delivered upon graduation from high school four years later.

In June 2009, I received the letter in the mail. It was a fun surprise considering I had completely forgotten about it!

I opened the letter and recall being blown away.

Apparently it was hard to take it seriously at age 14—the letter was filled with a bunch of silly, immature inside jokes—but it did have a few gems:

  • Reflections on the Present—most notably a desire to carve my own way rather than be defined by the impressive path that my older sister had established in high school.

  • Goals for the Future—a lofty ambition to play baseball at Stanford, which I somehow did accomplish!

But like most 18 year olds, I put the letter away in a filing cabinet and never thought about it again…

As fate would have it, on January 5, 2016—my 25th birthday—I was cleaning out some old files and found the letter.

I immediately decided to re-ignite the practice...

How to Structure the Letter

In writing the first letter on my 25th birthday, the time horizon I decided upon was 5 years.

Why 5 years?

Anecdotally, I have found that 5 years is the amount of time in which meaningful life change happens. When I thought about my own life, there were significant differences in my situation, mental state, and ambitions from age 15 to 20 to 25, so it struck me as an appropriate interval for the letters.

Note: 5 years was the number I chose, but you can adjust to your preferences. Some people may start with a 1-year time horizon to pull forward the opening process—that works too!

The letter format is mostly unstructured, but I try to have some degree of content consistency across them.

The four areas I am sure to address in each letter:

  1. Reflections on the Present

  2. Changes to Make

  3. Goals for the Future

  4. Fun & Crazy Predictions

A few specific topics within each:

Reflections on the Present

This is all about deconstructing the present. It functions as a deep journaling session that requires significant introspection.

Some prompts that may help:

  • What is working?

  • What isn't working?

  • What is giving me energy?

  • What is draining my energy?

  • What relationships give me genuine pleasure?

  • What relationships are toxic?

  • What is surprising me about the present?

  • Are my current habits aligned with my goals?

This portion of the letter is a bit of a brain dump—highly therapeutic.

Changes to Make

This is a natural outflow of the reflections on the present.

Review the responses to what is draining your energy, what relationships are toxic, and what habits are leading you away from your goals.

What changes do these responses suggest I need to make in my life today?

For every 1 degree a plane veers off course, it misses its target destination by 1 mile for every 60 miles flown. The lesson: Tiny deviations from the optimal course are amplified by time—off by a little now means off by a lot in 5 years.

The ability to adjust in real time is critical.

Goals for the Future

The key topics to cover related to goals:

  • What are my big picture, ambitious long-term goals?

  • What are my short and medium-term goals that will set the appropriate trajectory?

  • Why am I trying to achieve them?

  • What would winning the next 5 years look like?

  • What new habits or systems would be necessary to achieve these goals?

  • What are my anti-goals? This is a new addition and *very* important.

The goals section of the letter is my favorite part of the process. It requires you to zoom in and out in a way that is very clarifying.

Fun & Crazy Predictions

I finish each letter with some fun…

What are my crazy predictions for what the future will look like in 5 years?

You're writing to your future self, so this is the chance to have some fun. These predictions tend to be pretty funny—and wrong!—when you read them in 5 years.

Go crazy!

Early Reactions & Learnings

Since I wrote the first one on my 25th birthday, I started opening the letters on my 30th birthday in 2021.

A few early reactions and learnings from the opening process:

5 year plans are basically useless

I was way off on predicting where I'd be in 5 years.

Life simply changes too much in a 5 year span—especially in your 20s and 30s. Having a 5 year plan is fine if it provides value via structure and focus, but recognize that it's probably going to have to adjust.

Reject the dogmatic pursuit of 5 year plans—be nimble and agile as you grow.

Focus on systems and habits

My reflection on the alignment of my systems and habits with my goals was the best predictor of my achievement of said goals.

Making adjustments and course correcting habits in real time was the most impactful part of the reflection.

The physical writing process forced a level of honesty and introspection that led to real changes.

Learn to dance sober

In my first letter, I expressed some disappointment:

"The only way I'm comfortable dancing in public is when I'm drunk. I want to change that."

If you can dance in public while sober, you're truly comfortable with yourself.

Let's all learn to dance—poorly but proudly!


The process of writing a letter to your future self forces deep reflection on the present and thoughtful rumination on the future.

I've written 7 letters to date. All 7 have led to meaningful newfound clarity and real-time adjustments that have contributed to new growth and progress.

I cannot recommend a practice more highly.

I handwrite the letters and store them in a cabinet, but if you’re looking for a more technology-enabled solution, there are tools like FutureMe that should do the trick.

To summarize, the letter to your future self:

  1. Reflections on the Present: Deconstruct the present. What’s working? What isn’t?

  2. Changes to Make: Review your reflections. What changes are required to improve your life today?

  3. Goals for the Future: Establish your short, medium, and long-term goals for the future. Establish anti-goals to avoid winning the battle but losing the war.

  4. Fun & Crazy Predictions: Have some fun and make some wild predictions for the future. Close with some flare!

So today or on your next birthday, give this practice a shot. You won’t regret it!

I’d love to hear what you think. Share this article and tag me @SahilBloom with your experience with the letter to your future self. I’ll be retweeting the best responses in the days ahead.

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