Write a letter to your future self.

4 years ago I received a letter I wrote to myself 10 years ago. A letter I had completely forgotten writing…

“The following is an e-mail from the past, composed 5 years, 8 months and 27 days ago, on September 18, 2006.

Imagine my surprise when I received an email containing a letter I had written to myself, which I had completely forgotten about. It was a letter my twenty year-old self had written to my twenty six year-old self, who in the midst of pondering where his path laid, decided that it was a good idea to write to his future self.

It was.

Re-reading it, the letter remains as poignant and relevant today as the day I received it. I’m surprised today, as I was when I read it for the first time, at how many of the things I grappled with then — dealing with uncertainty, questioning my purpose, pondering about the people in my life— I continue to do so today, albeit at a different level. Questions I hope I’ll continue to wrestle for the rest of my life.

A man never steps in the same river twice. For he is not the same man and it’s not the same river.” — Heraclitus

Understandably, there was a lot of trepidation back then as a 20 year-old trying to find his place in the world. I’m definitely more certain today; of how life is inherently uncertain, and how much more there is to know and how little I do know. Because of that, there is a lot of trepidation today. Understandably.

Even though we change as we grow, I guess many of us never really change on the innermost level, but we simply develop layers and nuances superposed on that core and become a different version of ourselves.

It’s strange, isn’t it? To look back at our younger selves and to feel that a version of yourself can be so distant and unfamiliar, when that person couldn’t be more you than you, and at one point was the version of you. And that someday in the future, you’ll look back and feel exactly the same way about who you are now.

Back to the letter. I haven’t looked at it in awhile, and since I’ve been wanting to do this for awhile now, I thought it’s a fitting moment to revisit the letter, and while I’m at it, write my future-self a new letter.

Below are selected excerpts of the letter, interspersed with my commentary.

It began with some preamble about what was happening back then when I wrote that letter: I was having a Java (programming language) exam next week and I was about to enlist in the army.

Then I asked about my folks.

How’s your folks? How are they doing now that they are older? Are they still socializing as much as when you were young? Have you been good to them??

Except for a health scare for my mum two years ago, they’re doing great. Although they no longer party as much (Yup, my parents were pretty wild. In a good way) Have I been good to them? Let’s see, I’ve moved abroad and I don’t nearly see them as much as I’d like to. So, no…pretty low on the filial piety scale in the past few years 🙁

I asked about my close friends; if I’ve remained close with them. If they’ve remained in my everyday life. If not, how are they and where are they now?

Thankfully, I’m still in close contact with most of them. Sure, a few have drifted away, but I have also been fortunate enough to have gained a handful of new ones.

You wanted to travel as much as possible, you wanted to live life to its fullest and see as much as possible. Are you still that same guy?

I did, I moved abroad. I’m not sure if I travelled as much as I wanted to ever since I wrote that letter. But I have been on a spectacular journey inwardly.

I asked about my dog, then a 5 months old puppy, and if he’s still around.

Fortunately yes. The love of my life continues to win hearts with those dreamy eyes and his Zen-like demeanour. Bringing him overseas was one of the best decisions I’ve ever made.

I asked about my ambitions and if I have achieved what I wanted to achieve.

Well. I’ve tried but I haven’t succeeded by conventional standards, but in many other non-conventional ways it’s a resounding YES.

I even took the opportunity to bust my own balls.

You speak so much sense, did you put money where your mouth is?

Thanks, wiseass, I think I’ve walked the walk. Although I didn’t know that I would be doing it on a tightrope.

Growing up, sports dominated my life. It was fitting that I asked if I continued to stay active.

Sadly, no longer team sports. Mostly, I’ve only been gymming and running the past 5 years. And since my younger self-hated the gym and running, he’s in for a treat.

Somehow, knowing of my tendency to ruminate and sometimes take things a tad too seriously, my younger self even dished some pretty solid advice that’s applicable even today. I reminded myself that if I were ever in doubt or struggling to “To take it easy, and to re-evaluate my life and ask: what do you want?”

Thank you! No, thank you.
You’re hilarious. No, you are hilarious!
*repeats ad infinitum.

One of the most important things I’ve learned over the last few years is that important questions are meant to be asked over and over again. Because there a million ways to answer a question, and you never know when you’ll stumble upon a new or interesting one, and how it might fundamentally change you.

What would I tell my 20-year-old self?


The older I get the more I enjoy wrestling with myself, and seeings others around me do so. In my experience, I’ve often found that the darkest paths are often the most illuminating. That magic tends to spark at the outer edges; in the realms of uncertainty, discomfort, and failure. In the moments when I’m failing and flailing. Because it’s in our struggles where we find out more of who we are. Where we discover the nuances and feel the undulations.

“The sea gets deeper as you go deeper into it.” — Venetian Proverb

I invite you to write a letter to your future self. Because it’s worth capturing the moment for posterity’s sake. Besides, the year is winding down and it’s the perfect opportunity to take some time for yourself and reflect on this year.

Who knows what tomorrow may bring.

If you’re struggling right now, maybe when you receive this letter in the future, you’ll look back and laugh at yourself. At how silly you were to have worried so much; if only you knew things were about to get better. If so, let it then be a timely reminder for you to appreciate what you have in front of you, and not give your current situation any more weight than it deserves. It too shall pass.

Or perhaps, you’re enjoying a good run at things right now and things may not be as rosy in a year from now as they are right now. You’re in pain and you want it to stop. Then you’ll be able to draw strength from the present moment, having taken the time to deepen your appreciation and connection with it.

We should celebrate both the bad and the good for what they are because they play the role they need to play for us to become who we need to become.

The way I see it, either way, you can only win.

Here’s how you can do it

Since that letter was mostly a series of questions, I thought this time around I’ll introduce some structure to it.

I divide the letter into two parts: Professional and Personal, and I and use the 4 steps below for each of them.

  1. Current mood & state of affairs — How you’re feeling, what’s happening in your life right now? What are your fears and motivations?
  2. Questions for your future self — What are grappling with now? What are you curious to ask your future self?
  3. Aspirations for the next year — What do you hope to achieve?
  4. Stop, Start, Continue (3–5 things you should stop doing, start doing, continue doing)

Don’t fancy yourself as a writer? Don’t worry. You don’t have to write an essay. It doesn’t matter if you choose to elaborate or jot down bullet points. Of course, the more detailed your entry is, the more fun it’ll be to read it in the future. What’s important is that you do it.

I promise you it’s fun. That fifteen minutes I invested back then is still paying dividends today, and will continue to do so. My favourite kind of investment.

Sounds fun? Try it yourself here > write a letter to your future self here.

I’ll leave you with how I ended that letter 10 years ago.

Remember to take the time to tell the people close to you how much you appreciate them.”

Truer words have never been spoken, my young padawan.


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