The Five-Year Letter


As I have done with groups of students for several years now, it is now your turn to write the Five-Year Letter. The assignment is to write an essay in the form of a letter addressed to the adult you will be five years from now. When you finish your letter, you will seal it into the envelope, address it, and turn it in. In the spring of the year 2023 I will mail the letter. No one will read the letter before it is mailed nor in the case it is returned. Letters which are returned and remain unclaimed for two years will be destroyed.

Address the envelope to yourself at the address where you can be most sure there will be someone who can get the letter to you. If you are unsure of your address, you may place a sticky note with your email on it so I may request a current address later. Do not put a return address on the envelope. I will need that space to add a return address when the letter is mailed.

What to Write About

You may write anything you want, as long as you keep thinking and writing until five minutes remain in the period. You will seal the envelope at the end of this period. The letter is a private affair between you and the future you. Do not share it with others during class today. You may write about anything you think will interest the person you think you will become, but these are the things former students have said they enjoyed reading about the most:


  • your feelings about high school as you leave
  • your values now—what matters to you and why
  • your friends now—who matters to you and why
  • your favorites now:
  • current politics—in Orlando, in the Central Florida area, in Florida, in the United States, in the world
  • current conditions and activities: What’s going on in economy and business, science, the press, the arts
  • foods, clothes, styles, possessions
  • music, songs, TV shows, movies, art, books, plays
  • personalities, sports, teams, groups
  • school subjects, places on campus, school activities
  • your worries and concerns


What are your predictions:

  • for the world: What will conditions be like? What areas will have hostilities? economic or political changes? population or energy problems?
  • for the nation: Politics: Who will be president? vice‑president? governor? mayor? Economics: What will economic conditions be? How much will a new car or house cost? at what interest rate? Technology: What will have been invented? What products will have been improved? how?
  • for the city and school: What changes will have occurred in Orlando? at Dr. Phillips High?


  • Where will you be living? What will your ties to Orlando be?
  • What education will you have had? Where? How successful will you have been in school academically? Socially? How happy will you be with your education?
  • Will you be working? What jobs will you have had? How much will you be making? What further advances will you be looking forward to?
  • What will you family situation be? Will you be married or single? Will you have children yet? What will your relationship be with your parents, brothers, and sisters?
  • What will have been your biggest successes? What ambitions will you have fulfilled? Which will still lie before you? Which ambitions will you not have fulfilled?
  • What will be important to you? Who will be important to you? What will your biggest problems be?


Write down all the advice you can think of for the person you will be at about 23. What attitudes should your future self have? What might you forget over the next five years and need to be reminded of? Can you give your future self any advice about handling disappointment if all your dreams haven’t come true? Tell your future self what you should be doing over the next ten years.

Time Left?

Include more information on the people most important to you this year. Who helped you? Whom would you like to get in touch with five years from now? Remind yourself.

Write yourself a short fill‑in exam on life at Dr. Phillips during your high school career. Be sure to enclose an answer key; you might forget more than you expect to.


Many thanks to my online AP colleague, the inimitable Skip Nicholson of South Pasadena High School (CA), for this fabulous assignment!

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