I Wrote Letters to My Future Self for Nearly Two Years. Then I Asked AI to Analyze Them.

A $0 self-reflection habit that gave me more clarity than most life coaches.

For close to two years now, I’ve been doing something that sounds a little strange when I say it out loud:

every three months, I write a letter to my future self.

The habit started after a retreat I went on in March 2024. One of the exercises was simple: write a letter to the version of you who exists 90 days from now. That’s it.

I tried it once in an airport terminal on my way home, and it stuck.

Since then, every quarter, I’ve sat down for an hour, usually at a coffee shop, and written one of these letters. Where I am in life, what I’m working through, what I hope the next season looks like.

I E-Mail each one to a close friend, schedule it for three months out, and when the day arrives, I read it and write the next.

It sounds small, almost too simple, but it’s become one of the most valuable things I do. When you read these letters back to back, you start to see your life differently. You catch patterns you’d never notice in real time. You actually see your growth instead of assuming it’s happening.

And recently, I added one more step. I saved all the letters into one document, uploaded it into AI, and asked it to objectively analyze the growth of the person inside that file.

More on the process, the prompts, and what I learned in a minute.

But before we get there, I want to share the exact template I use to write these letters: the questions and sections that have helped me get clarity every single time. It’s simple, practical, and you can copy it straight into your own life.

Because the short version?
This entire practice feels like watching a time-lapse of your own identity.
It’s something anyone can do.

And to be honest, I just think it’s really cool…

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What These Letters Actually Are

A 3-month letter is basically a snapshot. Nothing fancy. Just a way to pause your life every quarter and check in with who you are, where you’re going, and what actually matters.

When I first started, the letters were messy. Some long, some short, some chaotic. Over time, they naturally evolved. I paid attention to what helped me reflect clearly and what didn’t. I’m still refining it, but this is the version that keeps me organized and makes the writing process simple instead of overwhelming.

Here’s the template I use today:

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THE 3-MONTH LETTER TEMPLATE (Simple + Effective)

1. Where I Am Right Now
A quick snapshot of your life today.

2. Where I’ll Be in Three Months
What you imagine the next season of life looking like.

3. How I’ll Feel
The mindset or emotional tone you want to carry into that season.

4. What I’m Hoping For
A few things you want to make progress on (work, relationships, health, writing, finances).

5. What I’m Proud Of So Far
The things you accomplished or handled well over the last quarter.

6. How I Want My Relationships to Grow
How you want to show up for the people in your life.

7. Mindset Shifts I’m Working On
What you’re trying to let go of, and who you’re becoming.

8. A Message to My Future Self
Short. Honest. Usually the sentence you most need to hear.

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This is the version I’ve settled into because it keeps me focused and makes each letter easy to compare with the last one. And the moment you stack a few of these together, the patterns start to reveal themselves.

If you want to see the exact letters I’ve written, just message me. I’m not including the full versions here because they contain personal and financial details. Not trying to gatekeep — just trying to be somewhat responsible, haha.

Next, I’ll show you the exact prompt I used to analyze all my past letters and what came out of it.

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The Deep Work: How I Analyzed My Letters (And the Exact Prompt I Used)

Once I had all my letters in one place, I got curious. I wanted to know what someone else, someone unbiased, would see if they read every version of me over the last two years.

So, I did what any reasonable person would do in 2025:
I uploaded the entire document into AI.

And here’s literally the exact prompt I typed (corrected for spelling, because I am clearly not a prompt engineer):

Using the following document, objectively analyze the growth, identity development, patterns, and recurring themes across every letter.

Give me:
1. An executive summary of who this person is becoming
2. The major identity shifts
3. The areas the person improved
4. Gaps or blind spots
5. What the next phase of their life trajectory likely looks like based on the writing alone

Nothing fancy. Just honest curiosity and a Google Docs file.

And then I asked a few follow-up prompts:

1. Create a personality model based on the letters.
2. Give me a future trajectory analysis.
3. Summarize this person’s strengths and mindset based on the writing.

Again… not expert-level prompting. But it got the job done.

And the result was honestly kind of crazy.

Without oversharing everything, here’s the gist of what came back:

• It picked up on identity shifts I never would’ve noticed on my own

• It highlighted how my confidence, discipline, and emotional maturity changed over time

• It revealed patterns in my writing that showed where I’m growing and where I get stuck

• It traced my career path, creative evolution, financial behaviors, and relationship growth

• It projected what my next few years will likely look like if those patterns continue

Reading it felt like someone had built a time-lapse of my personality, my habits, and my underlying beliefs, the stuff that’s hard to see while you’re in it.

And the wildest part?

It felt like having a CEO-level coach sitting across the table, breaking down my life objectively.
Except the coach was free, instantly available, and only useful because I’d done the upfront work of writing honest letters every quarter.

Next, I’ll share a few takeaways from the analysis. Not the personal details, but the bigger ideas that might help you understand yourself better if you try this too.

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What I Took Away From This (And Why I’m Sharing It)

I’m not someone who thinks AI is going to fix your life. I’m not handing over my decisions or letting a model tell me who I am. But in this very specific case — analyzing two years of honest writing, it ended up being incredibly useful.

Not in a “this is your destiny” way.
More like a neutral third party showing me patterns I wouldn’t have seen on my own.

That’s really why I’m sharing this with you.

Because when you combine real self-reflection with a tool that can read everything you’ve written and look for themes, you get a level of clarity that usually only comes from talking to a really good coach, mentor, or counselor. And people spend thousands of dollars trying to get exactly that kind of perspective.

The difference here is that the entire input is you.
Your writing.
Your patterns.
Your life.

I’ll save a few of the outputs in case you ever want to see what the analysis actually looked like.

I’m not posting them here because they include personal and financial details but trust me, it was genuinely impactful to read through.

And here’s the part I want to emphasize:

You don’t let the analysis dictate your next move.
You treat it the same way you’d treat advice from someone you respect: helpful, interesting, worth considering, but not absolute truth.

The real value is the combination:
your reflection + your writing + an objective lens that helps you see what’s already there.

That’s the entire point of this exercise, and honestly why I think it’s worth trying. Granted, you will need to stick with it for a while.

Closing Thoughts

I’m sharing all of this because the combination of these two things — writing a letter every three months and then stepping back to analyze the bigger picture — has been one of the most grounding practices I’ve ever added to my life.

It forces you to pay attention.
It makes your growth visible.
And it turns vague “I think I’m changing” feelings into something you can actually see.

Not because the letters are perfect.
Not because the analysis is perfect.
But because together, they give you a clearer sense of who you are and who you’re becoming.

If you want to try this yourself, steal the template. Modify it however you want. Write your first letter today and schedule it for March. Send it to me if you want! I would love to support your growth.

You don’t need the AI part right away, just get honest on paper.

The true clarity comes from the consistency.

And if you ever want to see how I wrote mine or what the analysis actually produced, just message me. I’m happy to share pieces of it privately.

At the end of the day, this practice has reminded me of something simple:

You don’t need a five-year plan to change your life.
You just need to check in with yourself more often.
Quarter by quarter, season by season, letter by letter.

Please, just get intentional with your life!!!

And if you do it long enough, you’ll eventually look back and realize you’ve built something meaningful, one honest snapshot at a time.

See you next week.