Receiving a letter from your past self can feel strange, even when you wrote it yourself. The email arrives between 8:00 and noon on the day you chose, and it can catch you in the middle of an ordinary task. Read it once, note what has changed, and write back as a new letter with a date of its own.
The email arrives, and that is the moment to slow down
The email holds your letter as plain text. Under the letter is a footer with an unsubscribe link, and that link is the one thing to be careful about. Clicking the link in the footer opens a page that asks you to confirm. Once you confirm, all letters to that address stop, including any you have scheduled, and you cannot undo that on the site.
So before anything else, keep your attention on the letter, not the footer. Open the message somewhere quiet, if you can, and give yourself a few minutes. You do not need to respond straight away. The letter has waited for years, so it can wait for the length of a cup of tea.
Reread it before you react
Read the letter once, all the way through, without writing back. Your first reaction may be a rush of feeling about the person you were. Let it come, and do not argue with it yet.
On that first read, notice which lines surprise you. Notice which lines you would now write differently, and which ones still feel true. Those two groups will guide the rest of the routine.
You may find that the tone is more hopeful, or more anxious, than you remember writing. Both are worth noting.
If the letter asks a question, you can answer it in your head for now. The answer belongs in your new letter, not in a reply to the email.
If the letter brings up something painful, pause and let it be. You can come back to it tomorrow, and a doctor or counselor can help if the feeling lingers.
Notice what has changed, and what has not
Make two short lists on a page: two things that have changed since you wrote the letter, and two things that have not. Keep each item to one sentence. The changes may be large, such as a new home or a new job, or small, such as a habit you dropped. The things that have not changed are often the most useful to notice, because they show what you have kept.
Write two things that have changed and two things that have not, one sentence each. Add one line on how the difference between them feels to you.
Be fair to both lists. A change does not have to be an improvement, and a constant does not have to be a failure. Write what is true, in the words you would use today.
Some changes will sit uneasily with you. That is normal. Write one sentence about how the change feels, rather than trying to settle it in a single afternoon, and let the feeling stay on the page while you go about your day.
Write back to the person who wrote it
Write back as a new letter, with a new delivery date. Do not reply to the email, because the email is a delivery, not a conversation the service will carry for you. Start with the date of the old letter, say what you noticed, and answer one question it asked. Then ask one question of your own.
Choose a new date and write as you normally would. The letter arrives on the day you chose, sometime between 8:00 and noon in your time zone. The site sends nothing when you write, so keep your own copy of the new letter, with its date.
Reading words from a younger, more anxious version of yourself can stir mixed feelings, so let the first wave pass before writing back. The service only delivers to future dates, so if you want to try writing to a past self, keep that letter in a notebook.
Keep the old letter and the new one together
Store both letters in one place, with the dates written at the top of each. Over the years, pairs like these become a record of how you have changed, and of how fast. A folder, a notebook or a shared note will do, as long as you can find it again.
Save the email as well as your own copy of the text. Your copy holds the words, and the email holds the date it arrived. Keep both with the new letter, so the set stays complete.
The service does not tell the writer when a letter cannot be sent. A copy you keep yourself is the only record you fully control, so make it the main record rather than a backup. The site sends no reminder on the day either, so put the delivery date in your calendar.
A sample reply letter
This sample opens with the date of the old letter and says what changed. It ends with one question for the reader.
Dear [name],
I received the letter I wrote on [date] on a gray Monday, and I read it twice before I made tea. It asked about the job I was nervous about. I did change jobs, and the first year was harder than the letter suggested.
Two things have changed: I walk to work now, and I have a small garden. Two things have not: I still write in the mornings, and I still worry about money on quiet nights.
If you are still reading this, did you keep the walk?
[your name]
Write it now
Choose a date for a letter you will want to read back, and write it now. Keep it short, and note two things you expect to change and two you expect to stay the same. Put the date at the top, so that the reply has something to answer.