Here are 30 prompts for a letter to your future self, sorted into six small sets: Today, People, Proof, Questions, Promises and Wildcards. You do not need all of them. Pick three, answer each in two or three sentences, and you have a letter.
Short is fine. Three honest paragraphs will read better in five years than a long letter that tried to cover your whole life.
How to use this list
Pick one prompt from three different sets. Set a timer for ten minutes. Answer each prompt in two or three sentences, in the order you like, and do not stop to polish.
Then put “Dear future me,” at the top, sign your name, and choose a delivery date. If a prompt makes you freeze, skip it. Another one is waiting.
Two or three sentences is less than it sounds. Take “Which bill or chore annoys you most right now?” One answer: “The recycling. There are four bins now, and I still mix up which week is glass. If you have solved this by the time you read it, I am impressed.” A plain fact, how you feel about it, and a line to the person who will read it. That is all a prompt needs.
Which three to pick
The mix decides what kind of letter you get. A letter meant to cheer you up later works well with one prompt each from Proof, People and Wildcards. A time capsule needs Today, People and one Wildcard, because it is mostly about texture.
A letter that checks in on you wants Promises, Questions and Proof. You promise something small, you ask what happened to it, and you leave yourself a few facts to answer with. Whatever mix you choose, keep one prompt that makes you smile. If you cannot choose at all, take one from Today, one from People and one from Proof: texture, a person and something you were quietly proud of.
Today, in plain detail
These prompts catch the texture of an ordinary week. You will not remember it in a few years, and it is often the part you enjoy rereading most.
- What does a normal morning smell like this week, at home or on the way out?
- Which bill or chore annoys you most right now?
- What song, show or podcast keeps coming back?
- What did you eat yesterday that you would happily eat again?
- What are you carrying in your bag or pockets today?
People
Put people in the letter. Use their names, and say what they did, not only what you think of them.
- Who made you laugh hardest this month?
- Who do you wish you called more often?
- Who would you text first with good news?
- What did someone say lately that you keep turning over?
- Who is new in your life, and who has drifted away?
Proof
Your future self may need evidence that you were doing fine, or at least doing something. Give it to them in specifics.
- What can you do now that you could not do a year ago?
- Which hard thing did you get through this year?
- What did you stop doing that you do not miss?
- What are you quietly proud of?
- What did you learn the slow way?
Questions for the one who reads this
A letter can ask things the writer cannot answer yet. These are written to copy straight into the letter, so here “you” is the person reading it later and “I” is you today. Leave them open. You will find yourself answering them as you read.
- What will you have forgotten by the time you read this?
- Did the thing I am worried about turn out to matter?
- What time do you get up now, and what is the first thing you do?
- Who from this letter is still around?
- What do you know now that I am still guessing about?
Promises
Keep these small. A promise you can keep on a Wednesday is worth more than a vow about your whole life.
- What one small thing will you keep doing, starting this week?
- Which habit will you drop without guilt?
- What do you want to say yes to this year?
- What do you want to say no to?
- What would you try if you did not mind looking foolish?
Wildcards
When the other sets feel too serious, reach for one of these.
- What would your twelve-year-old self refuse to believe about your life now?
- What is the strangest thing you believe at the moment?
- If this week were a weather report, what would it say?
- What do you hope stays exactly as it is?
- Write one sentence you would like to read again on a rough day.
Build a longer letter
For a longer letter, take one prompt from each set and write a short paragraph for each. Six paragraphs of three sentences make a page that holds together and still takes less than half an hour.
The writing form takes up to 30,000 characters, so room is never the issue. If six paragraphs start to feel like homework, stop at four and send those.
The writing form takes much more than a page, up to 30,000 characters, but length is not the point. A letter you finish is better than a grand one you abandon.
A year is a good first distance
A first letter often works well at one year. The quick choices run from one day to three years, and you can pick any date up to 20 years ahead. We email the letter on that day, between 8:00 and noon in your time zone.
The sets age differently, which can help you choose. Promises and Proof read best within a year, while the promise is still yours to keep. Today and Wildcards get better with distance: this week's morning smell is a small curiosity next year and a real find in ten.
Copy your text somewhere before you save it. Nothing is emailed when you write, a saved letter cannot be edited or cancelled, and letters are stored as plain text, so leave out passwords and anything you would not want anyone else to read.
A sample letter built from three prompts
This one uses three prompts: “What does a normal morning smell like this week?” from Today, “Who made you laugh hardest this month?” from People, and “What one small thing will you keep doing, starting this week?” from Promises.
Dear future me,
The bakery aisle smells like warm bread at six in the morning, and I have started arriving early just for that. My daughter laughed at my terrible pun last week, a real laugh, the new one with a snort in it. I promise to keep Sundays empty: no errands, no email, just the long walk and a slow breakfast. I hope the walk is still happening. If it is not, start again this Sunday.
[your name]
A different mix gives a different letter. This one takes Proof, Promises and Questions, and it reads like a check-in:
Dear future me,
A year ago I rehearsed every phone call twice before I dialed, even the one to book a haircut. This week I called the landlord about the heating without writing anything down first. Small, but it is mine. My promise is one dreaded call a week, made before lunch so it cannot grow all afternoon. So: did I keep it? And the call I am really avoiding, the one to my brother, did it turn out to matter as much as I think?
[your name]
Write the next list yourself
Once you have used a few prompts, you will see why they work. Each asks for one thing you could point at, and each can be answered in a sentence. “What is on your windowsill?” works. “What matters most to you?” stalls, because it asks for everything at once. Write five of your own for next year's letter, and swap one in each time you write.
Write it now
Choose three prompts from the sets above and set a timer for ten minutes. Write your answers in your own words, add a date and send the letter. You can come back for the other twenty-seven next year.
