To write a letter to your future self, choose the date you'll open it, describe your life right now in ordinary detail, say what you're hoping for and worried about, and ask your future self a few honest questions. Then seal it somewhere you'll actually find it, and put the opening date in your calendar.
The ordinary details are worth more than you might expect. In a 2014 Harvard Business School study published in Psychological Science, students who filled time capsules with recent experiences underestimated how curious and interested they would be to reread them three months later. In a related experiment, people underestimated how much they would enjoy rereading about an ordinary day, while predicting their reaction to a special occasion fairly well. Today's small moments are easy to undervalue while you're living them.
Pick the date first, because it shapes what you write. A short gap suits specific plans; a long gap suits the bigger picture.
Six months: good for a goal or a change you're in the middle of.
One year: a natural checkpoint. Writing on a birthday or at New Year and opening it on the next one makes the date easy to remember.
Five years or more: for life-sized questions about work, home and relationships.
A moment, not a date: the end of your first year in a new job, moving day, or the day a course finishes.
Whatever you choose, write "Do not open until..." on the envelope and add a calendar reminder, so the letter doesn't disappear into a drawer.
Today's date, where you're sitting and what you can hear.
What a normal day looks like right now: work, meals, who you text most, the song on repeat.
What's taking up most of your thinking, including decisions you haven't made yet.
The people who matter to you at the moment, and why.
Something you're proud of, however small.
What you're hoping for, written as hopes rather than tests you might fail.
Something kind, in case things haven't gone to plan.
If the blank page stalls you, finish a few of these sentences and keep going.
"Right now, an ordinary Tuesday looks like..."
"The thing I keep thinking about is..."
"By the time you read this, I hope..."
"I'm nervous about..., and here's what I want you to remember about it."
"Are you still...?"
"What turned out to matter that I'm ignoring right now?"
"If things went differently than I planned, I'd like you to know..."
"The people I'd thank today are..."
"One small thing that made me happy this week was..."
Write to a friend. Address it to "Dear me" or your name, and use the voice you'd use in a long message to someone you trust.
Be honest, not impressive. Nobody else needs to read it. The messy, uncertain parts are often the most interesting later.
Keep it to a page or two. Long enough to capture your life, short enough to finish in one sitting.
Don't over-edit. A crossed-out line tells your future self something too.
Add a small extra if you like: a ticket stub, a photo or a list of what's on your phone's home screen.
Read it slowly, and notice what changed and what didn't. Be generous with your past self: plans that shifted aren't failures, they're information.
Then consider writing a reply. Psychologists Yuta Chishima and Anne Wilson asked students to write a letter to their future selves and then write back as their imagined future self, and the students who wrote back felt more connected to who they would become. You can turn this into a habit: answer the old letter, then seal a new one for a later date.
Dear You: Daily Letters is an iPhone app where you can seal a letter to your future self for anywhere from a week to five years; it opens in the app on its scheduled date, and you can reply and seal that reply for a later self. Your letters stay on your iPhone, with no account and no ads, plus an optional Face ID, Touch ID or passcode lock.
Get Dear You free on the App Store