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Letters to Your Future Self

Each year on my birthday, I write an email to my future self.

I've been doing this for two years.

This involves composing a new email with myself as the sender and recipient, then scheduling it to arrive in my inbox on my next birthday.

I was inspired to try this after listening to Sendhil Mullainathan sharing a similar idea on a podcast.

What is the content of the email?

This is completely up to you.

Mine looks like this:

  • What's on my mind—name the big things renting space in my head, and share the opinions or positions I have on them.

  • What did I finish reading lately—list the titles of books, and write down any key insights from them.

  • What's happening at work—be as specific as possible to share things that have happened recently, and things that are coming up that I'm excited about.

  • What's happening at home—same idea as work, the more specific the better.

How has practice been useful?

At first, I had no idea what to expect from a practice like this.

After two rounds, I've realized that the most important question, is the first one—what's on my mind.

When I read my most recent birthday email, I realized that something that I assumed had only been on my mind for the past 6-8 months, had actually been on my mind for the past two years.

When I probed a bit deeper as to why I had this disconnect, I realized that it was only in the past 6-8 months that I had actually made space to think about the thing that had been on my mind for a long time.

6-8 months prior to my most recent birthday is when our family went on our first vacation since the start of the pandemic. Apparently, that's where I found the space.

What I've learned from this practice so far, is that I need to find a way to cultivate the proper space—without going on vacation halfway around the world—to actually listen to the things that are on my mind.

What I find strange about this, is that I assumed I was actually doing this quite well.

Apparently not.

To me, that's an exciting realization.

Why should you consider this practice?

I'll leave you with two reasons:

  1. No one knows you better than you know yourself, which means that you might also be a great teacher to yourself. This practice allows you to travel through time and teach your future self a few things.

  2. One of my favourite psychological illusions is The End of History Illusion. It simply suggests that we are not good at predicting how much we will change in the future. This practice will allow you to notice the things that have changed, while also allowing you to question the things that haven't changed.

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