The Letter to Your Future Self
Today at a Glance
- On January 1, 2014, I wrote a letter to my future self just before graduating. Ten years later, I opened it, and it hit me hard. Everyone should do this.
- My core reflection: We have the answers, we just haven't asked the right questions yet.
- To write your own letter to your future self, cover four key areas: (1) Reflections on the present, (2) Vision for the future, (3) Changes to make, and (4) Fun predictions. Use a technology tool (like FutureMe) or store a physical letter somewhere safe. Set a calendar reminder to open it on the set date in the future.
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On January 1, 2014, I wrote a letter to my future self just before graduating from college.
On January 1, 2024, 10 years later, I opened it.
The experience, impact, and learnings hit me hard.
Everyone should do this.
In this piece, I'd like to share my letter, my reflections, and a simple process for you to write your own letter to your future self.
My Letter & Reflections
Here was what my letter said:
January 1, 2014
Hey Old Man –
If you’re reading this, it means you’re alive, so congrats on that, I guess.
I’m about to graduate and enter the real world, whatever that means, so it feels like an appropriate moment to lay out some hopes for my future:
1. I hope you married Elizabeth. Seriously, I hope you didn’t f*ck that up. She’s the best thing that ever happened to you.
2. I hope you’ve got a kid by now. I don’t want kids, but I imagine I might grow up at some point and change my mind on that. If you do have kids, I hope you’re a good dad. If you’re even half as good as your dad was to you, you’ll be great.
3. I really hope you’ve worked on yourself and grown up. You have a lot you hide from the world. You’re insecure. You compare yourself to everyone but yourself. You’re so afraid to fail that you always seem to choose the safe path. You’ve got work to do—don’t run away from it.
4. I hope you tell your parents you love them more often. They don’t know how much they mean to you, and that’s a shame.
5. I hope you live closer to family. You made your mom sad when you took that job. She smiled and said she was happy for you, but it was that sad smile that her parents gave her when she left for America. The smile of losing a child to a new world. Don’t let that be the case.
6. I hope you got closer to Sonali. Sibling love is special, but you’ve allowed your competitiveness to get in the way of that at times. I hope you’ve gotten past that and embraced each other in a new light. You can learn a lot from her.
7. I hope you’re working on something that feels meaningful. I don’t even know what that means, to be honest, but I guess it’s something like enjoying a random Tuesday.
8. I hope the friends you love and care about are all healthy and thriving. I know that’s probably impossible, so I guess I hope the friends you love and care about know you love and care about them. That’s all that matters in the end.
9. And finally, I hope you’ve had a little bit of fun along the way.
That’s all for now. I don’t know how you sign off a letter like this.
Goodbye for now, I guess.
My immediate reaction upon reading the letter was to be overwhelmed with emotion. The raw, real voice of my younger self coming through the words felt jarring after ten years.
As I re-read the words, one major realization jumped out:
The answers are within you—you just haven't asked the right questions yet.
I was as dumb, arrogant, and insecure as they come when I wrote those words, but the letter reveals a wisdom and clarity that I had yet to action upon.
I knew there was a brighter path ahead. I just had to start asking the right questions to start walking it.
How to Write Your Future Self
The exercise was so impactful—both the writing and the reflecting—that I believe everyone should sit down and do this.
You can establish your own time horizon. Common choices are one year, five years, and ten years.
I'm old fashioned, so I typed and printed the letter, preferring to store it in my personal safe than to use technology. That said, you can use online services (like FutureMe) or simply email the letter to yourself and set a calendar reminder.
The structure of the letter is entirely up to you, but the few areas that I would recommend addressing:
- Reflections on the Present
- Vision for the Future
- Changes to Make
- Fun Predictions
A few specific prompts that may help spark your writing within each:
Reflections on the Present
Think of this as a deep journaling session that requires significant introspection.
Deconstruct the present version of you:
- What's working?
- What isn't working?
- What's giving me energy?
- What's draining my energy?
- What relationships give me genuine pleasure?
- What relationships are holding me back?
- What's surprising me about the present?
If done well, writing this portion of the letter should feel highly therapeutic.
Vision for the Future
Think of this as a vision board of your hopes and aspirations.
Consider your compass heading:
- What is my ideal life on the day when I open this letter?
- What are my big picture, ambitious long-term goals?
- What are my Checkpoint Goals that will set the appropriate trajectory?
- Why am I trying to achieve them? What are my true motivations?
- If I opened this letter and everything was in flow, what happened along the way to spark that?
- What are my Anti-Goals? What perils do I want to avoid along the way?
Create a crystal clear image of that ideal future. Zoom out and zoom in.
Note: If you're interested in goal-setting for 2024, you can download my free Annual Planning Guide template here.
Changes to Make
This is a natural outflow of the reflections on the present and the vision for the future.
Review the responses to those prompts:
- What changes do I need to make in my life today to create that future?
- What daily actions will make that future a reality?
Remember the 1-in-60 Rule: For every 1 degree error in heading, a plane will miss its destination by 1 mile for every 60 miles flown. Tiny deviations from the optimal course are amplified by time—off by a little now means off by a lot in a few years.
Make changes to set the optimal course.
To add some lightness, finish the letter with some fun:
- What are my fun or crazy predictions for the future?
- What AI robots are taking over the world?
- What terrible TV show is still, inexplicably, on the air?
- Which crazy family member is still giving you terrible birthday gifts?
You're writing to your future self, so this is the chance to have some fun.
Hello, Future Self!
Today is January 10, 2024.
Over the next few weeks, sit down and write a letter to your future self.
10 years from now, 5 years from now, 3 years from now, whatever.
Reflect on where you are, where you hope to be, and the changes you need to make. Take action to make that envisioned future a reality.
Remember: The future is yours to create. You have the answers, you just need to start asking the right questions.
P.S. I opened and read the letter on an emotional live recording. You can find the raw, uncut footage of that experience here.
P.P.S For those who were wondering, yes, I married Elizabeth. And yes, we had that kid.