Updated on 12.23.07

A Letter to Myself in Ten Years

Trent Hamm

Many, many people write letters to their past selves, advising their earlier selves to avoid mistakes that they’ve made. I thought it might be interesting to take the opposite approach and write myself a letter today to read on my fortieth birthday.

Dear Trent,

Today is your fortieth birthday. Your son is twelve years old, your daughter is ten years old, and you’ve been married for fifteen years. Right now, I can scarcely believe that’s possible. I don’t know what frustrations and joys you will have experienced between now and then, but I just wanted to pop in with a little reminder of the things you value now, so that maybe you’ll sit down and use your fortieth birthday as an opportunity to really look at your life and make sure that it’s still centered around the things that you value.

I guess that’s the first thing I want to say. Right now, take a few hours and set it aside to really reflect on your life. You probably don’t remember the day to day realities of your life when your daughter was a newborn and your son was two, but you spent it working full time at a job and at two side businesses, plus you devoted time to your children and your wife, spent time on your hobbies, and still squeezed in a bit of time for reflection, too. The times in your life that you’ve been melancholic have been the same ones where you failed to take time to reflect on things. So, take that time right now. Go for a walk in the woods and think about where you’re at right now.

When you get back, do these things.

Take that wonderful wife of yours, the mother of your children, into your arms, give her a kiss, look her straight in the eyes, and tell you that you love her. Right now, she is the emotional center of your life, and even if that has changed somewhat in the intervening ten years, let me assure you that right now, as I write this, she is the reason to get up in the morning. Don’t let little aggravations get in the way of things.

Give each of your children a hug, too. You and your wife used to spend every evening completely devoted to them, and they’ve likely grown into interesting people as well. You’re probably wondering where the time went, and asking yourself when your son turned into a budding young man and your daughter transformed from a soft, snuggly little baby into a nuanced and thriving child. Hug them both, and don’t let these last few years of their childhood slip past. Take some extra time to spend with them, and never hesitate to let them know that you love them.

Think about what you really want to do. Right now, I’m planning on spending much of my thirties making the strongest possible foundation I can for you, one of financial security for you and your wife and those kids. Why? So you can do some amazing things now. Go on a few deeply memorable vacations in the next few years. Take your family and visit every continent in the world. Do some things that will build your family’s connections, but also enable your children to grow and see new things. I’ve spent much of my time over the last few years worrying about how I will be able to take care of those children, but they’re growing up now and the worry should be less, so use those resources you’ve got to experience some new things.

Right now, our family’s plan is to build a new house when I’m about your age. We want to build it out in the country, and we’ve already started planning for it financially. Ask yourself seriously, is this still the dream? Talk about it as a family, and then use those financial resources in whatever way you think is the most valuable for you.

Most of all, never, ever stop dreaming. Your dreams of writing made The Simple Dollar possible and has (hopefully) led to some great writing opportunities over the last decade. Don’t stop. Listen to what your heart is telling you and do it. You should be close to complete financial freedom now – take that leap and just run with whatever it is that’s in your heart.

One final thing: she still wants to go on that Bahamas trip, you know. See if you can leave the kids with her parents for a week or two and just go. It will probably be the best thing you guys have done since, well, your honeymoon.

Best wishes,
Your twenty nine year old self

No matter where my life goes between now and then, the contents of that letter will mean something when I read it again in 2018.

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  1. na0 says:


    i’m a frequent reader, first time commenter.
    thank you for this entry.
    it’s a great idea that i’ve heard of people doing time and again,
    but it just now clicked for me and i will be doing the same for myself.

    thanks again.

  2. JasonY says:

    Great letter. I did the same thing about three years ago (I was 35 then), but I did it on a website. There’s a service out there called futureme.org. You can write an email that will be delivered to you at any time in the future. Pretty neat.

  3. anon says:

    Good luck. When I read this, the first thought that hit me was, “You’re going to cry when you read this if you’ve gotten divorced between now and then.”

  4. feefifoto says:

    This is lovely. Your wife, kids and friends are very lucky.

  5. ablemabel says:

    I love this idea! I’m totally going to do this.

  6. Amanda says:

    Hey Trent, you don’t have a slightly younger brother just like you, do you?

  7. Sharon says:

    hmmm…what about a slightly older brother just like you??

  8. vh says:

    How ’bout one that’s about, ohh, 20 or 25 years older? :-)

  9. Emma says:

    Wow, I had no idea you were 30. :)

  10. Amanda says:

    Hm. We’ve got a seven brides for seven brothers thing going on here. Hopefully Trent has a lot of bachelor brothers. :)

  11. May says:

    I hope that when I’m 29, I will think just like you :)

  12. Daisy says:

    lol. :D that was a great letter though.

    I did this once and it was cool. I never thought about writing to my past self though. I figured she wouldn’t get to read it anyway. :)

  13. Kathy says:

    You can actually send that letter to yourself at FutureMe.org. Great idea!!

  14. Renee says:

    What a great letter. It is alway so nice to see someone who truly adores his wife and family. Maybe people should write letters to themselves every year so they can remember why they married their spouse in the first place and list all the good qualities that they first saw in each other. After being married for almost 18 years, having a good marriage is not hard, it just takes focusing on the good and not dwelling on the bad/annoying.
    Best of luck to you and you family. I hope you and your family have a very Merry Christmas. Your hearts see to all be in the right place.

  15. Beth says:

    i really look forward to your articles and topics, but this surpassed my expectations. The timing is perfect with the new year coming and the holidays right here now.
    Planning to be where I want to be in 10 years, and staying on track needs something emotional and creative vision to get there.
    Thanks for reminding us to dream, and I believe you wil get there too.

  16. Rob in Madrid says:

    you’d be surprised how fast time goes when you get older. When I was 40 my Dad told me the next 25 years will go in the blink of an eye. My wife turns 45 this year (ok 2008) and she wants out of the corporate world by 55 and I said you’ll blink your eyes and it will be here!

  17. Gayle says:

    Believe me ten years can totally change your life and in very unpredictable ways. On my 45th birthday, my husband and I were in London celebrating 25 years of marriage and his successful career. The company paid for the trip.

    On my 55th birthday I was in Africa, 8 years divorced, with my kids scattered around the world. I paid for this trip, doing volunteer medical work. There was no way I could have anticipated this.

  18. Nancy Latham says:

    I love your letter to yourself 10 years from now. I am many years older than you are and from my prospective and knowing how fast time goes by, I would reccommend revisiting that letter every year. Merry Christmas to you and your family.


  19. Sarina says:

    When I took a bereavement class after my husband died, we participants each wrote a letter to our future selves at the end of the year. The facilitator mailed our letters to us in the new year, about a month or six weeks later. I was amazed to get the letter in the mail, even though I knew about it and had written it. It was a very powerful exercise. I never thought about applying this same concept to any other part of life. I also never thought about extending the time. Thanks for the idea!

  20. Laura says:

    show that letter to your wife right now – at least paragraph #3.

  21. Meg says:

    You know you can actually write your future self emails/letters at http://www.futureme.com. You can write to your next week self, your next year self, or yourself in 30 years. The site will then email you at whatever date you specify.

  22. FourPillars says:

    Great post – I like the advice about not worrying about the annoying stuff..(which I do).


  23. I have already done that four years ago. A friend of mine keeps it safe with her, and she’ll send me the letter when I ask for it.

    Thankfully, I just can’t remember anything I wrote. The only thing I remember about it is its size: eight full handwritten pages.

    I’ll get it back as soon as I get married, which will happen by April or May, 2008.

    ~ Mario, from Brazil

  24. Marta says:

    What a beautiful letter. Thank you for sharing such a personal note with all of us.

    This letter truly shows what really matters (easy to see during the holidays but is often clouded during the rest of the year): family, friends and love.

    And I definitely agree with Laura, show your wife that letter!!

  25. Will says:

    Dear 30 year old me (from 40 year old me),

    I appreciate all the wonderful advice you have for me, and I know it’s straight from y(our) heart, so thank you.

    It brings tears to my eyes to remember how it seemed like we had so much figured out, and planned, and how hard we ran on that hamster wheel trying to “make” things work. Only later did we realize that we were operating from a core set of rules and assumptions which had to be questioned.

    Things have worked out wonderfully, but so completely different than we ever imagined.

    In these last ten years the kids have grown even more amazing, if you can imagine that, and we’ve seen them try on so many different phases and attitudes. Yes, those early days are a blur now, but you’ll be glad to know that our time with them remains just as precious, no matter how grown-up they are and how much they change. Please continue to take lots of pictures, especially of the little one, to help us remember later.

    There have been some extremely hard times as well, most of which we thought were unexpected, but now, reading your letter, I realize we did kinda have premonitions. Deal with ’em when the time comes, and know we survived.

    I’m taking more time to reflect nowadays than you would ever imagine, so we learned that lesson well! We would have done well to have started taking more “me” time a bit earlier than we did… turns out, it wouldn’t have slowed down our progress toward our real goals at all. ‘Course, those goals changed a great deal over time, but that’s for you to find out ;-)

    I would only ask you to be open to the inevitable change which blows through our life like a sudden wind from the west. Determinedly sailing into that wind for so long was exhausting… relax, it takes us good places.

    Thanks for reminding me what mattered back then, what our values were, and what a big-hearted guy we were! Wish I could buy you a beer.

    I’m currently working on a letter to our 50 year old self. God Only Knows where we are and what we’re like then, but I’ll bet that SOB has some good stories for us!

  26. sexyback says:

    who said you were going to be alive in 2018? im not trying to be mean but dont you think your alittle to old????

  27. michael says:

    You did a great job. Actually I am from Beijing, I am a student, and my teacher is Japanese, he ask us to do a homework is about what you would like your life to be 10 years from now. until I found you litter, I have some afflatus about this work, so thank you!

    best wish

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