Writer's Toolbox

The Incomparable Power of Writing Yourself a Letter

This is the first post in a series, The Writer’s Toolbox.

The successful warrior is the average person with laser-like focus
— Bruce Lee

Today. It’s all we have. I understand the appeal of focusing on the ‘now’ to get things done, but personally, prefer a little occasional time travel.

I’ve found a quick, simple activity that helps jolt me awake. A different way of paying attention. It disrupts the continuous and into the fresh space comes a brief sliver of noticing.

I simply write myself a letter … from the future.

‘Future You’ Has Things to Say

Here’s how it works.

Choose a moment: the end of today, the week, or the month. Or a year from now. Whatever timeframe you need.

  • Take out pen and paper—Yes, I do sometimes use a typewriter—You can use a laptop or phone notes app. Whatever works for you but analog makes it feel like correspondence.

  • Maybe set a timer to keep it short.

  • Date your letter on the future date you’ve chosen (year from now, month, week, day, whatever.)

  • Without pausing, start writing, as though to you, now.

For example, if you’re stuck with your day, write a quick note to yourself from this evening about how the day went. How thankful you are for getting … done. That you, say, took a walk, made that tricky phone call, drank enough water, got to bed on time. Whatever it is that feels impossible or improbable. You might find out what the day needs to hold for you to make it through.

Or ‘you at the end of a trip’ writes to ‘you, now,’ who is overwhelmed trying to pack for that trip. The big picture breaks into the daily round and says, “Remember why you’re here. Remember why you’re going on the trip.”

Or perhaps you’ll write about what the summer was like, dated from when the school year starts, only you're really writing in May.

It’s like planning but the other way round: from the future.

You don’t need to mail your letter. Just set down your thoughts and put them where you can find them again. Prepare to be astonished when you read them on that date.

Though, hey, you can put the letter in the mail. I did this month. It was a bit astonishing to get a note in my own handwriting saying how well the month went—all the impossible bits did get done, after all—only I remember writing it in utter disbelief.

You will be amazed at what comes out when you try this. Some of it will be rubbish, of course, but some ideas will be profound and disarming. It might be ‘what you actually want.’

An Annual Planning Tool

Six years or so ago, I joined Michael Nobbs for a getting-things-done type of online course. Many of us on the course formed an ongoing group. We met weekly and worked live online together, putting one creative foot in front of the other. We still work together several times a week.

(This was long before the pandemic. We were ahead of the game!)

Michael can no longer join us, for health reasons. But each summer we still set aside several Saturdays to plan the year ahead. We celebrate victories and think through unfinished projects—decide whether to abandon them or press on. We dream a little and reset our intentions for the year.

In that last session, we set a timer and each write ourselves a letter dated a year ahead to the day, saying how the year went. This was how I came across this odd time-travel notion of writing to yourself from the future.

The first time I did it something exciting happened.

It Couldn’t Be More Effective!

That first time, I wrote my annual letter in late summer. The following spring I would turn a milestone age. Life was very busy. Six kids: two beyond college, two in college, and two teens still being homeschooled, with speech and debate tournaments, and me teaching a high school class at a homeschool co-op an hour away. This was, of course, pre-pandemic.

To my surprise, as I wrote the letter, out came exactly what I would like to do to celebrate my birthday, still months away. Something like, “I’m so thankful we were able to take time as a family, right after college exams and just before everyone’s summer jobs started, and spent a week in a rented house on Cape Cod to celebrate my birthday.”

What?! Wow. That was specific, and nothing like anything I’d ever asked for. It seemed to come out of nowhere. But on reflection, made sense. Swirling plans and outside demands had gathered into a jammed calendar and scattered family.

As a result, my husband was out walking with a coworker one lunchtime in early spring. The co-worker asked what we were doing for my big birthday. My husband mentioned my desire to rent a house at the Cape for a week.

“This family in our church has just the place!” the co-worker said. “The house belonged to their parents. Now they rent it out by the week. It’s a great family space. We’ve stayed there and it would be perfect for you all. And it’s half-price before the season.”

We went.

And I was a complete convert to writing letters to myself from the future.

The impossible trip happened, partly thanks to a ‘Letter to Myself’ the year before. Enjoyed in a sketchbook.

A Smith-Corona Silent-Super typewriter came on the trip and a glue stick. But I forgot scissors! Never mind; ripping is fun. The map folds out. This was the first time I tried to use a typewriter in a sketchbook. It took some fiddling to figure out how many lines would fit on the page, and how long lines could be. I set the margins and left them for the week, and noted them in the back of the book.

Wing’s Island, Cape Cod, MA - colored pencil sketch done on the hot, hazy beach. Hand-sewn sketchbook, about 6 x 4-inches, closed - a gift from one of my kids. I like to fill up an entire tiny book on a trip and be done with it, the story of that one season. If there are blank pages, glued ephemera and a final reflection can often do the trick. Or leave them blank!

Not Simply Magical Thinking

This is not some kind of magical thinking. It is just another tool to help uncover what you really think. Obviously, at some point, you have to do the work.

But if you tend, like me, to be scattered, or wildly enthusiastic and prone to wander to the shiny and the new, or prone to getting immensely discouraged and stuck, why not give it a try? I have learned to be laser-focused, about a few things at least.

Much fear can come from obsessively picturing the future. Putting things off increases that fear, says Steve Chandler in Time Warrior. This defined, brief letter idea seems a healthier way of acknowledging the reality of looming deadlines or stuck desires, and seeing a way through to ‘done.’

Of course, using a fabulous little typewriter for the task only makes it more enjoyable. Or a great pen. But that is all irrelevant compared to just putting down some words and finding out what your future self has to say.

It’s how I managed to get this post written at the close of a crazy month.

Try it.

And let me know how it goes. I’d love to hear from you in the comments below!

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