A Story of a Man Who Wrote and Mailed Letters to His Future Self



(Today’s guest post is written by language coach Aaron Myers, who shared a story with me of writing and mailing letters to his future self between the ages of 25-50. Blown away by that, I asked him to write to share his story.)


Benny’s blog post, What I Would Say to Myself Five Years Ago and Five Years From Now reminded me of my own letter writing adventure.

While Benny’s letters were inspired by a writing project called #trust30 and Corbett Barr’s question, my journey began with fear and has lead to a life filled with receiving letters from myself.  In the beginning though, it began with a conversation.

It was 1995. I was twenty one, a junior in college and preeminently occupied with the idealistic irrationality of youth. But then one night I got scared.  I was enjoying a good talk under an expanse of Kansas stars with a friend. Conversation ranged in and out of dreams and challenges and faith and eventually, our fears.

Chris shared her heartache over a relationship with a father who – while a good man – never really understood her.  They were like two strangers, who after sharing a home for eighteen years, had now parted company.  She cried at the loss.  And I shook with fear.

The proclamation that her father did not know her set me back and I wondered at the overwhelming challenge that one day fatherhood would bring.

That night as I walked through quiet streets to my apartment on the edge of town, I decided that I did not want that lot in life.  I determined to do something to avoid such a fate, to avoid raising a daughter with whom I had no relationship.

And so I did what any reasonable English major would do.

I got out a sheaf of college ruled paper, brewed a pot of coffee and wrote a long letter of challenge and encouragement and warning to myself to be received on the day my first daughter was born.


After finishing that letter, a half a pot of coffee remained and I still had a chest full of hopes and fears. My biggest hope at the time was to get married and to someday have a family.

This prompted a letter to a wife I did not know, introducing her to the 21 year old version of the man she was marrying.  Next I wrote a letter to my first child on his or her 16th birthday, sharing my hopes and dreams for their future and urging them to call me back to a life of passionate purpose if it seemed I had slipped into a life middle aged sleep walking.

And this was my biggest fear at the time, of one day turning 35 and discovering that I had grown apathetic and dull and had lost the passion, faith and sense of purpose I had as a twenty one year old.  And since there was ample evidence around me that this was a path down which too many adults traveled, I set about writing letters to myself at 25, 30, 35, 40, 45 and 50.

Those letters were letters of exhortation.  I received my third letter on my 35th birthday two years ago and have it with me here in Turkey.  “Happy 35th.” it begins, “You’re getting old.”   As I read through it, I am amused by my 21 year old self.  But the challenges rings true.  Here are a few of the things I wrote:

  • Remember back to your junior year and your life of faith.
  • Don’t stop growing.
  • Don’t grow old and apathetic.
  • If your heart has stopped breaking for the poor and needy, find it in you again.
  • If you’re married, love your wife like no other.  
  • Love your kids.  Give them your time, not stuff.
  • If you have a daughter, remember your talk Chris.

These exhortations and others greet me as a forced reflection on life, causing me to stop and take stock and reconsider what it means to live from the  passionate core of who I have been called to be. For me that core was and still is a core centered in life giving faith. All of life flows from that core and makes me who I am.  For others it may be something else. For all of us though, as Steven Pressfield reminds us, “there is an enemy.”  

I believe this enemy works to defeat us with what Chris Guillebeau has called “a contagious pattern of settling for what is good enough.” We must fight against this, against the natural tendency toward complacency and the slow death of losing focus.

Writing letters to our future selves can be for us the immunization we need against this plague of mediocrity. That is what it has been for me. Each time I have received one, it has been a transforming experience of remembering what is important, of reflecting on where I’m at and of thinking about the years to come.

Each letter has a sticky note with instructions and I have placed them in the charge of my mom who has faithfully mailed each one on time.

I remember my wife’s eyes when she looked up twelve years ago from the letter I had written her as a young college student. I received my “daughter” letter five years ago when Sonora was born.  I’ll receive my next letter when I turn 40.

I’ve grown a lot from my 21 year old self. I’ve learned to recognize that many that I looked down upon as stuck in a life of mediocrity, were really leading passionate lives of direction and purpose. My father was one of those. I have heard too many testimonies of his impact on the lives of others to doubt it any longer.

The thing that most impresses me about my twenty one year old self, is that I focused the letters not on a my future vocation or on a bucket list or anything really pertaining to what I would do. These things are important, but they are at the peripheral of the core, of who I would become. Who I am is much more important than what I do.

I would encourage you to consider this exercise.  Think about those things that are most important to you, about family, about dreams, about the core of who you are.

Brew a cup of coffee, grab a pen and paper, and write. Write to yourself. Write to those you love. Leave a legacy in the future that will call you back to those things which are most important in life.


Written by Aaron Myers.  Aaron believes everyone can learn another language.  You just need a little help.  That’s why he writes The Everyday Language Learner and why he has developed the soon to be released EDLL Guide to Getting Started, a new eGuide including three great interviews,  twenty audio lessons and much more. Stop by the site and check it out.


Photo by cicciofarmaco

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38 responses to A Story of a Man Who Wrote and Mailed Letters to His Future Self

  1. Aaron:
    I love this idea. I think you have the makings of a book here. At the very least, an updated version of the Wear Sunscreen song that was everywhere in the 80’s. (or 90’s?)

    But here’s my question to you….is your mom available to mail our letters? If so, I’ll ship a pile out to her right away. 🙂

    Great post. thanks for sharing.

    • Well, I’ll have to ask my mom about that one. Sounds like an idea for a new income stream for her. She has been so wonderful with this and just reminded me last week that she has the next one (I’ll be 40 in 2013!!!) ready. Thanks for the kind words and have a great day.


      • Aaron,
        Great article! I was in high school when you gave those letters to mom and I remember how weird I thought you were!! Now though, my non-teenage self thinks it’s a wonderful idea! Maybe I’ll have to write one to each of my girls. And, in case you’re wondering, mom showed me where the letters are so that there is a back-up to make sure you get them.


  2. Aaron, this was an amazing and moving piece. I can only imagine the look on your wife’s faces how she must have thought how lucky she was and fallen back in love with you all over again. (I must have a chat to my husband. hmmmm)

    I like the idea of writing a letter to my future self and my future kids. I have been writing letters to my kids once a year on their birthdays telling them how proud i am of their accomplishments, listing all the things they did because i know they will forget. Telling them the highlights of the year. Then, when they are old enough, maybe when they have kids of their own, i will give them the letters.

    Thanks for sharing.

    • Your husband has some pressure now!! Maybe he’s been writing secret letters that you don’t know about. Hmmm…

      That’s amazing about the letters you’ve written for your kids. When they get older, they’ll appreciate it more when they get it. That is truly so cool!!!

      Oh and Aaron left you a reply but didn’t reply to the comment directly so you didn’t get an email about it. Just wanted to let you know so you can see it.

      Thanks sister from another mother!

    • Uh oh, looks like Aaron is going to put a lot of people in the dog house with this one :).

      I think what you are doing in terms of writing letters for your kids is no less impressive or touching than what Aaron did for himself. I wish I had letter to look back on. That’s awesome!

  3. Annie,
    Thanks so much for your kind words. I really love the idea of writing to the kids in the here and now. So tangible and something they can take with them. I will make a note to begin this year. Do you give them to them each year or are you just saving them?

    Thanks for the great idea and thanks for your response. Have a great day!


  4. I really enjoyed reading this post, Aaron. I love the idea of writing letters to your future self.

    I find that going back and re-reading old journals from years past helps me to refocus on what is important and prioritize where I’m going. But I might have to try the letter idea since I haven’t been very consistent about writing in my journal lately.

    • I haven’t been writing in my journal as much as I should as well. For two years when I lived in Taipei and Sydney, I wrote in a journal, on the computer, every single day. I’m so glad I did because I can read an old entry and relive that day. Writing in a journal is great though!

      Oh and Aaron replied to your comment but didn’t reply to it (if that makes sense). He just left another comment. Just wanted to let you know that too!

      Thanks Lindsay!

  5. Thanks Lindsay. Journals are a great tool as well though I realize that some of us take to journaling more than others. The letters add an intentional element of exhortation that my journals don’t have though it is always instructive to read back through one of my little black Moleskines. Thanks for the encouragement.


  6. Wow, this could be an incredible powerful technique. It’s kind of a step on from writing your own eulogy, which I know is a popular technique.

    Recently I wrote my ideal day. In detail. I asked my wife to do the same and so we could compare. She got to the second sentence and decided to set up her own jewelry business as that is something she really wants to do.

    A Goal is a dream with a plan and a deadline.

    • I’ll leave the eulogy writing to others and hope I’ve earned a good one! I like the ideal day idea. I’ve heard about it elsewhere but have yet to do it. Maybe soon. Thanks for the kind words and it has been powerful for me. Maybe for others as well.

  7. What a fabulous idea and to think you did that at the young age of 21. Aaron I’ve never met you or visited your place but I am SO impressed young man. And yes, trust me hon, you are still young!

    What a fabulous idea. So you went up to the age of 50. Well, I’m past that mark so does that mean I’m screwed? Just kidding..

    I was very touched that you could think to do that I really am so impressed. The things we can learn from what we have already been through in our lives and to be reminded from our younger self. To even come up with that is what amazes me.

    You can tell I’m off in na na land here. Sorry, I’m just so blown away by your post. Thank you so much for sharing it with all of Benny’s buddies. I already know it’s been well received but I’ll speak for all of those who have yet to visit this post, very well done my friend, very well done.


    • Adrienne,
      I’m blushing. Thank you for your very kind words. I am glad I can be an encouragement and can only hope that this post will help others live more reflective, purposeful lives. At 21, 50 seemed a long ways off. Now it seems I should perhaps have bumped it up a few decades. Hopefully the wisdom of time will help me carry through though. Thanks again for your encouragement and have a wonderful day.


  8. What an awesome read Aaron. I love the idea. I wish I would have done this when I was younger, but I did write for 15 years in a journal, which brings everything back into focus. Reading about your journey was wonderful and touching. 🙂

    • Richard,
      Thanks for the encouragement. Glad you have been a journaler. I find journals and invaluabel source for reflective living. Have a wonderful day!


  9. Hi Aaron, (Hi Benny!)
    This is a wonderful and inspiring story. I never thought of doing this even though, at the age of twelve, I believe, I found this poem by ray Bradbury that your story brought back to mind,
    I think, as Kathy said, that this would make an interesting book!

    • Lori,
      Thanks for your great comments and for sharing the poem. So fun. But a book? I’ll have to think about that one – “The Art of Intentional Reflection” or something like that.

      Have a wonderful day!


  10. What a powerful story!…So glad I stumbled upon you and will now subscribing to your blog. I definitely journal everyday, but may consider kicking it up a knotch. 😉

    • Kenya,
      Thanks for the encouraging words. Journaling is a wonderful exercise and I am glad you are writing daily.

      Have a great day!


  11. “Who I am is much more important than what I do.”

    This is the most important sentence right here folks…This is what it’s all about.

    Great read Aaron.

    I think my own letters would have been contrived pieces of false wisdom and Powerball numbers which of course wouldn’t work in the future because they were the past numbers. See..I wasn’t as thoughtful as you were back then..Probably from clouded brain cells.

    Anyway, dig the concept.

  12. And it has been a journey of finding out just who I am. I remember this guy telling how he had walked into a meeting of big wig execs and asked them to each introduce themselves without mentioning what their jobs were. Silence! We are more than a bucket list or a job description or a blog. The tough part is of course cutting through the clutter that our society throws at us that confuses this. Working hard to succeed at this.
    Thanks for the encouraging words and have a great week.


  13. Hey Aaron,

    This is really an amazing story. I got teary eyed while reading. I am planning to this very soon. Thanks for the inspiration.

    Regards, Louie Sison

  14. Aaron,

    This is a great exercise that I have heard of but never put into action. Your personal story is very inspring an encourages me to reap from the many benefits this activity could have in my life. Plus I like to write so I am all over it. Thanks for sharing.

  15. This is a great idea, i know what i will be doing this weekend.

  16. After reading this, I feel like I should do it. I think initially I would find it hard to think of something to say to my older self. But that’s what would make this so interesting. I wonder what I would say. Maybe I should do this and write a post about it.

    • Steve,

      I’ll look forward to seeing that post! I’m not sure what I would write now either? Perhaps if I had some big life change coming up I’d want to sort of force a bit of reflection into my future.


  17. Aaron – I’m so honored to be a part of this incredible journey you’re on, if only by going to the mail box and that you trust me enough to do just that. Through many moves and life changes I’ve hung on to those letters. My worst fear is that I’ll miss a date but so far so good. I’m so proud of the man you’ve become. You write beautifully.

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