A letter made of questions is the easiest honest letter there is. You do not have to narrate your life or sound wise. You only have to ask the person reading it to tell you what happened.
Below are fifty questions that work well when they are asked years in advance. Pick a dozen, number them, sign the letter, and you are done.
Why a letter of questions works
Questions take less effort than statements. When you write “I am tired this month,” you have told your future self one thing. When you write “Are you still tired in October?” you have asked them to look back, compare and report.
There is another benefit. A question you cannot answer today gives the letter a reason to exist. The reader opens it with a task: find out what the answer turned out to be.
How to ask
Ask real questions, ones you cannot answer from where you sit. “Do you still live here?” is a real question. “Are you happy?” is too big to answer in one word, and it tends to get a flat reply.
Keep each question short and aimed at one thing. Avoid stacking three questions into a single sentence, because the reader will answer the easiest one and skip the rest. Address your future self directly, with “you.”
Daily life
These questions record the texture of an ordinary week, which changes faster than people expect.
- Where do you buy your coffee now?
- What is on your keyring these days?
- Which app do you open first in the morning?
- What do you cook when you are too tired to cook?
- What does your commute sound like?
- Which shop on my street has closed?
- What is the most annoying noise at home?
- What is your phone like now?
- What did you pay for lunch last week?
The people around you
- Who did you last hug?
- Who did you lose touch with, and was it all right?
- Who is the newest person in your life?
- Do you still call the same friend on Sundays?
- Who made you laugh hardest this year?
- Whose advice do you still follow?
- Who do you wish you had thanked?
- Are we kinder to the people we live with?
- Who do you still argue with?
Work and money
- What are you paid to do now?
- Did the plan I am making survive?
- Which skill did you pick up that I cannot imagine?
- Do you still dread Sunday evenings?
- What are you saving for?
- Which job did you turn down, and do you regret it?
- What do you wish you had started earlier?
- Who is your favorite person at work?
Body and weather
- What hurts these days?
- Do you still run, swim or walk the way I do?
- Is your street still noisy at night?
- How do you sleep?
- What do you eat for breakfast?
- Has the winter gotten milder or harsher?
- Did you finally see a doctor about that thing?
- What does your favorite season feel like now?
Inner life
- What are you avoiding right now?
- What made you proud this season?
- Which worry of mine turned out to matter?
- What do you believe that I would argue with?
- Are we kind to ourselves yet?
- What did you forgive?
- What do you want more of?
- What would you tell me tonight?
Playful
- What replaced the app I love?
- Do you still sing in the kitchen?
- Which song is everywhere now?
- Did the houseplant survive?
- What is the silliest thing you spent money on?
- Do you still have the blue jacket?
- What would surprise me most about your Wednesday?
- Do I get a pet?
Pick twelve, not fifty
Fifty questions in one letter will tire the reader. Choose twelve, with at least one from each group, and put the ones you most want answered first.
Number them. Numbers make the reading feel like a conversation, and they let you answer in the margin later, one by one. Keep at least two questions that are easy to answer, such as the coffee one. They give you a way in on the day the letter arrives.
Make a few of your own
The best question in any letter is usually one only you could ask. “Is the dog still afraid of the vacuum?” does more for you than a clever question from a list. Add two or three of your own, drawn from this month: the thing you keep wondering about, the argument that is not finished, the plan that might not happen.
Be gentle with the heavy ones. A question such as “Did we get through it?” is fair to ask, and it may be hard to read on a bad day. If you are unsure, put it near the end, after the easy ones.
What the answers will do
On the day the email comes, you will not just read the questions. You will answer them in your head, or aloud, and you will notice which ones feel funny and which ones feel heavy. The answers teach you what you took for granted.
If you like, copy the letter into a document and write the replies beside each question. Then write a new set of questions to the person you will be after that. A letter that gets answered tends to start a series.
We email the letter on the day you choose, between 8:00 and noon in your time zone, and a saved letter cannot be edited or cancelled, so keep a copy of your twelve questions.
A letter of questions
This sample is questions only, and it is complete as it is.
Dear future me,
Here are some things I would like to know. 1. Do you still flinch at that song? 2. Did the plant live? 3. Who did you call last Sunday? 4. What do you cook when you are too tired to cook? 5. Is the street still noisy at night? 6. What did you forgive? 7. Are we kind to ourselves yet? 8. Do you still have the blue jacket? 9. What would surprise me most about your Wednesday? 10. What did you start that I was afraid to? 11. Which friend turned out to be the real one? 12. What are you paid to do now? Answer as many as you like. Skip the ones that hurt.
[your name]
Write it now
Choose twelve questions from the groups above, and put your favorite first. Add a line at the end that lets your future self skip any question they like. Pick a date a year or more away, and send it.
