Letters that arrive on time
Clearing out my father's desk I found a letter he had written to himself at twenty-two, in a sealed envelope marked open at 40. He had opened it. There was a second note folded inside, written in the same hand but eighteen years older, and it said only: you worried about the wrong things.
I have thought about that more than almost anything else he told me directly. Partly because of what it says, and partly because of what it proves: that he had been twenty-two once, and frightened, and had had the presence of mind to send a message forward.
Why writing to your future self works
There is a straightforward psychological reason, and it is not mystical. Most of us experience our future self as a stranger — someone we are happy to lend money to and pile obligations onto, because they are not quite real. That is why we book things for next month that we would never agree to do tomorrow.
Writing a letter to that person does something small and specific: it makes them a person. You have to picture them. You have to decide what they will care about. And once your fifty-year-old self is someone you have addressed by name, it becomes noticeably harder to hand them a mess you could have dealt with yourself.
It works in the other direction too. Writing to who you were at twenty is a strange and useful exercise, because it forces you to be specific about what you actually know now that you did not know then. Most people find they know about four things. They are usually not the things they would have guessed, and they are almost never about money.
What to put in it
The common failure is to write a motivational speech. Your future self does not need a speech. They have had years of speeches and are, if anything, slightly sick of them.
What they cannot get anywhere else is the texture of right now. What the flat looks like. What you are worried about this month, in detail, including the parts that are embarrassing. Who you are in love with and whether you have said so. What your mother sounds like on the phone. How much things cost. What you do on a Wednesday evening.
This is the thing that will hit you in ten years, and it will hit you sideways, because you will have forgotten the whole texture of the period and the letter will hand it back. The advice ages badly. The details age like wine.
One more thing worth including: what you are currently putting off, and why. That sentence has a way of reading as an accusation ten years later, which is exactly the point of sending it.
Letters to other people that you do not send
The other kind of letter is the one written to someone who cannot read it. Someone who died. Someone you fell out with and are not going to call. Someone you loved at nineteen who is now a person with a mortgage and no interest in hearing from you.
Grief counsellors have used this for a long time, and it is not really about the other person. It is about finishing a sentence you never got to finish. The relief people describe afterwards is not the relief of being heard. It is the relief of having said it out loud in any form at all.
If you write one of these, my only suggestion is: do not send it. The urge to send it is strong and almost always serves you rather than them. Write it, keep it, read it in a year.
Pick a real date
A letter with no delivery date is a diary entry. The date is what makes it a letter.
Five years is a good first distance. It is far enough that you will be measurably different and close enough that you will certainly be around to read it. Ten years is the classic. Anything past twenty starts to feel like writing to a descendant.
Put the date in your calendar as an event. Not a reminder — an event, with a title you will understand when it surfaces. Then put the letter somewhere you will not encounter it accidentally, because a letter you reread every few months stops being from anyone.
The version for parents
If you have children, there is a variation worth knowing about. Write to them at eighteen, and write it now, while they are small — not the advice, the reporting. What they are like at four. The word they say wrong. The way they fall asleep in the car.
You will forget all of it. Everyone does; the brain is not built to keep that volume of ordinary detail. And the person who most wants that detail, when they are twenty-five and trying to work out who they are, is them.
My father's letter did not tell me anything about what to do with my life. It told me that he had been young, and scared, and had kept going, and that eighteen years later he judged his own fear to have been aimed at the wrong target. That is not advice. It is company, sent forward through time, which is rarer and worth more.
Write yours this week. Pick the date. Put it in the calendar. It takes twenty minutes, and it is the only message you will ever send that is guaranteed to reach someone who is interested.