Why I write letters to my future self
How sending letters to myself in the future helps me reflect on my past
The start of a letter
I was burnt out when I moved to New York in 2019. I had just graduated from university, and decided to start work without taking a proper break (#toomuchhustle). That summer, I finished a daily journal with “fill-in-the-blanks” reflection and gratitude prompts. I wasn’t very diligent with the journal by the end because it started to feel like I was trying to over-optimise life (“science has shown that a daily routine of gratitude improves your baseline dopamine levels by 25%”—you know the vibe).
Right before tossing the journal in the (recycling) bin, I flipped through the pages once more. It was one of those burnout moments of doing something random to distract myself. Surprisingly, I found an interesting suggestion hidden at the back: send a letter to the future self reflecting on the last months. Without overthinking about it, it seemed like a cool thing to try. So, I found a website called FutureMe, and wrote about nothing and everything. And then, I sent my letter to the future…
Six months later in December 2019, I got an email ➡️ 📥
I had completely forgotten about it, and reading it was genuinely illuminating.
I wasn’t fully aware of it then, but it was clear from reading the letter that I was really lost. I was being really hard on myself by pointing out all the things I needed to improve. It’s good to want to be a better person, but not when it comes from a place of shame. And in contrast to my self-criticism, I was impossibly ambitious about what I should accomplish in six months.
The letter gave me a third-person perspective that I had never seen before. It was revealing to read about my past self—so, a few days later, I was already writing the next letter.
What I write about when I write to the future
I write and receive a new letter every six months. In each letter, I like to mention aspects that reflect the bigger picture of my life at the time:
What happened in the last six months
My reflections on how I feel about my life
Goals, ideas, aspirations, priorities…
However, I still keep the structure loose enough to avoid overthinking about what to write. Some examples of streams of consciousness from the past:
I have been getting stronger and gaining good ground, but I think the thing that remains is the fact that 1) I am still working on […] being more consistently happy, 2) improving some things that I've noticed around my self ([…] like being bothered about not being unique), and 3) [having] a more stable and fulfilled attitude toward my work and the C word (career).
From a letter written on July 19th, 2019
“I need to move into myself. I need to lean into my own delusion a bit more. Be a little crazier and trust my inner gut and instinct. The one that says "I can do that, I can learn that!". I need to move away from "hmm maybe that makes more sense, I need to plan for the future..." As long as I have some money, it will all be ok.
From a letter written on January 5th, 2020
It's been a pretty rocky and crazy 2020. It started off with a bang […] we got married in February right before everything shut down and we moved to Delaware. I lost my job at the end of March, […] then I built a shed from scratch [in the summer] to reconnect with my building side. [Then] we moved to France amidst the pandemic [...] let's not forget the crazy, crazy pandemic that has been scaring and scarring humanity emotionally. I'm hoping that by the time you get this, things are a lot better?
From a letter written on December 31st, 2020
Still writing, still learning about myself
Although I shared extracts from my letters, they are not meant to be shared. I try to express myself as openly as possible in letters because I know they’re just for me. And I’ve been able to learn a couple things from my honest reflections…
Looking back, I often didn’t spend my time on the “right” things (and I still struggle with this). Sometimes, this frustration would translate into unrealistic expectations. In my first letter, I expressed what I wanted to accomplish in six months: become conversational in Korean, become skilled at sketching and drawing, be able to sight-read and compose music, start learning acrobatics, perform stand-up at a few open-mics, publish multiple blog posts… I wanted to do all the worthwhile things at same time, but I was obviously setting myself up for failure.
Nowadays, I’ve grown tired of pursuing empty definitions of success that take energy away from what matters. I try to spend my time more intentionally and focus on what makes me feel energised. And as a result, I have more realistic goals because I don’t feel so desperate to find time to do meaningful things.
I’ve also learned from my letters that my values and aspirations have stayed relatively consistent. I want to let go of empty expectations. I have a fierce drive to continue learning new skills and challenge myself. I don’t want to experience life passively and stay inside my comfort zone. I want to be a better person, for myself and to those around me. I want to be less afraid of judgement. And I want share my thoughts more openly and more often, just as with this blog post.
Where I write from here
I think there are a few new directions I’d like to go with the letters. For one, I want to see if writing them every three months is more worthwhile. And although I appreciate the loose structure, I want to ask consistent questions in each letter to snapshot specific things over time; questions like, “what is your biggest worry right now?“
I also want to experiment with the format beyond reflecting; it would be interesting to capture more things, like a time capsule. Such as listing significant purchases I made in the last six months. Or add and tag a couple photos of my most notable recent memories. Or things I want to remember later like articles I read or podcasts I listened to in the last months. A brief sprinkle of history.
If it wasn’t for my burnout that summer, I never would have started writing these letters. But it wasn’t a burnout that got me to write a letter, it just helped me find a little suggestion at the back of a journal.
Looking forward to reading the next one.
Thank you for reading, I appreciate it! 😊
Community question
I’m going to add a little question or prompt at the end of each post to create more of an interactive experience rather than just one-way communication. I’ll try to feature answers in the next post!
What is something that someone has done for you in the past that you will never forget?
Nice read, I want to write to my future self as well. I think I've written something a few years back that is supposed to arrive 10 years later, but would be more interesting to do quarterly or annual, to keep accountable to myself. Keep up the good writing, this was really worth it and inspirational :)
To answer the question of what someone did for me that I will never forget.. When I was in university, my father decided to cut me off financially and end all communication for reasons that are beyond me, and which I will probably never understand. It was a really challenging time in my life working through exams, complete finacial uncertainty, periods of extremely low confidence, social anxiety and being in a school environment that was so fundamentally different from my own values that I felt I was constantly wearing a mask.
During this time, I was fortunate enough to have met one of the most amazing human being on this planet. She invited me to move into her apartment, took care of my emotional health and with the help of her family, financed my living and food costs for the rest of my education. I've now married this person, taken her last name, and I will never forget what she did, and how she has always been there for me.
Inspiring! I will write my future self a letter. I like the idea of adding reminders in the letters, too. Thanks so much for sharing. To answer the question—I will never forget Nancy Hoffman, a dear ninety-year-old friend, reassuring me that the twenties are the scrambled egg years. Totally jumbled. Her words have gotten me through a lot of chaos!