SENTiment — More than a message.

Guide

Questions to ask your future self

A letter to your future self is hard to start because you are writing to someone you haven't met yet. Questions make it easier. They give the person you'll become something to answer, and they show you, years from now, exactly what you were wondering about today.

Below are fifty questions in seven groups. You don't need all of them. Pick the five that make you pause. Those are the ones worth sending forward.

How to use these questions

If you want a simple structure for the letter around them, our guide to writing a letter to your future self walks through one.

  1. Read the list once, quickly. Mark anything that makes you stop.
  2. Choose three to seven. Fewer, answered honestly, beats many answered politely.
  3. Write a sentence of context under each one: why you're asking it now.
  4. Leave some unanswered. A question your future self has to answer is the point.
  5. Choose when it comes back: a birthday, an anniversary, the end of something you're starting.

About who you are now

  1. What do you still believe that I believe today?
  2. Which of my habits did you keep, and which did you finally drop?
  3. Do you still laugh at the same things?
  4. What would you tell me I'm worrying about for no reason?
  5. What do I do every day that you'd give anything to do again?
  6. Are you kinder than I am? Harder?
  7. What song reminds you of right now?

About the people in your life

  1. Who is still with you that I'd be relieved to hear about?
  2. Did you ever make up with the person I'm not speaking to?
  3. Who did you meet that changed everything?
  4. Did you tell them, the people who mattered, while you could?
  5. Who do you call first with good news now?
  6. Is there someone I should be paying more attention to?
  7. Did you become the parent, friend or partner I'm hoping to be?

About hopes and plans

  1. Did you do the thing I keep saying I'll do "one day"?
  2. Was the plan I'm so sure of the right one?
  3. Where do you live, and does it feel like home?
  4. What are you building now that I haven't imagined yet?
  5. Which dream did you let go of, and was that relief or regret?
  6. Are you still curious? About what?
  7. What would make you proud of me for writing this?

About fears and hard things

  1. Did the thing I'm afraid of happen? Did you survive it?
  2. What got you through the worst year?
  3. What do you know now that I'd have needed to hear today?
  4. Did you forgive yourself for what I can't forgive myself for yet?
  5. What turned out to be smaller than it looked?
  6. What turned out to be bigger?

About ordinary days

  1. What does a normal Tuesday look like for you?
  2. What do you eat for breakfast now?
  3. What's on your nightstand?
  4. What smell takes you straight back to this year?
  5. Do you still have the [jacket, mug, car, ring] I love?
  6. What's the first thing you do when you wake up?
  7. What small pleasure do you never skip?

About the world

  1. Is the thing everyone is arguing about today still important?
  2. What invention do you use that I couldn't picture?
  3. What do you miss about the way things are right now?
  4. Did the place I grew up change?
  5. What would surprise me most about your world?
  6. What are you hopeful about?

About the moments that change everything

  1. You were just starting something new when I wrote this. Was it worth the leap?
  2. Who is the friend you laughed hardest with this year?
  3. What's the accomplishment you're quietly proudest of, the one nobody else noticed?
  4. How did you spend your last birthday, and who was there?
  5. What do you know about love now that I'm only beginning to learn?
  6. What was the best surprise of the years between us?
  7. What part of growing older turned out to be better than I feared?
  8. Which milestone (a wedding, a child, a home, a finish line) felt different from how you imagined it?
  9. When was the last time you felt completely, unexpectedly happy?
  10. What are you looking forward to now?

Questions to leave unanswered

Some of the best questions are the ones you can't answer for yourself: Are you happy? Was it enough? Did you become someone you'd like? Write them down anyway. You'll know the answer the moment you read them.

Are you happy? Tell me honestly.

Choose a date that means something

A question lands differently on a day that matters, like the birthday you're nervous about or the anniversary of the day you started. Pick a date before a round number.

With SENTiment you can write the letter now and have it arrive on the date you choose, typed, in your own handwriting, or as a voice letter if you'd rather hear yourself ask.

Keep reading

The person reading this one day will be glad you asked.

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