A Letter to My Future Self (and How You Can Write One Too)


Letter to My Future Self | Wit & Delight
Photo by Ksenia Kazak on Unsplash

I’ve seen a lot of letters to past selves. Here’s what I would say to my post-pandemic self, they read. Don’t be so hard on yourself. You are the only one you can count on. Slow down. You can’t go through life afraid to live it. You’re going to be so proud of yourself! I even wrote one in 2019, a tough love letter to my twenty-something self. But why look back? What about our future selves? What questions do we want to ask? What do we wonder?

The theme on Wit & Delight this month is “Show Up As Yourself.” So, I was intrigued to write about the possibility of change and speak to a portion of myself I don’t know. I want to explore how the future me might feel. I want to dedicate time to that mystery soul. This person could have children, not have children, experience loss, grow old, find growth, experience unknown pain, and develop new habits. When we write to selves about the past, we know them and there’s a pompous clarity in the writing. Sure, giving advice to our past selves is fun. But is it helpful? How can we best explore who we might become? How can we best break down the walls of the person we’re afraid to see? How do we write about the unknown?

I want to write a letter with more intention. I want to ask questions and discover what scares me about getting older. In a way, that’s what the most honest writing does for us anyway.

When I think about it, we are always (sort of) writing to future versions of ourselves. We write through dreams and aspirations, ideals, and healing. We imagine the future in great depth, struggling to center on the present. But, I want to write a letter with more intention. I want to ask questions and discover what scares me about getting older. In a way, that’s what the most honest writing does for us anyway. Right?

Okay, here goes nothing/everything.

Dear future self,

Hi, it’s me from the past. I’m thirty-five. I don’t know how old you are now. I’m envisioning you’re in your sixties. You’ve lived an entire life. You’re as old as your mom was when you wrote this letter. I guess this letter is sort of like inception. I’m so afraid to write this. I’m struggling to imagine who you are.

Can I be honest? You’re you, after all. Right now, I feel selfish. I want to tell you all the things I want in my life. I hope you got them. Right now, your thirty-something self is needy. I want a baby. I don’t want a baby. I want more money. I want to live within my means. Beyond my means. I want more time. I want to scoop minutes up and feel like I can’t possibly carry all the hours to the end of my driveway. I want everyone to live forever. I don’t want to experience deep grief. I’m so lucky. I’m so selfish. 

If you’re sixty, lucky enough to live until then, I know you’ve experienced pain by now. The deep kind, the oceanic kind, the kind that is so dark and expansive, you wouldn’t be able to explain it to me. Are you okay with that grief?

I read this quote in Susan Cain’s book Bittersweet recently (you should read it again and see how you feel). “If we could honor sadness a little more, maybe we could see it—rather than enforced smiles and righteous outrage—as the bridge we need to connect with each other. We could remember that no matter how distasteful we might find someone’s opinions, no matter how radiant, or fierce, someone may appear, they have suffered, or they will.” I didn’t mean to jump right into suffering. That must be my fear pouring through. You’ve always been a deeply melancholic person. You love sad music. You have an acute awareness of passing time. You have a joyful curiosity about specific beauty points in the world. Lately, I’ve identified with the Arabic proverb, “Days of honey, days of onion.” You are the definition of bittersweet. Are you still? 

I also read in Bittersweet that, as we get older, we find comfort with the passing of time. I imagine you don’t try and slow it down. You are a quiet way of being, a force of storied tradition, loss, and joy. Does that feel beautiful?

I’m sure you’ve turned toward many humans, loved them, held them, and cared for them. But I hope you’ve done the same for yourself. Somehow, I know you will.

I have some wishes, as well. I hope you transform your sorrow and longings into art. I hope you’ve written a lot of letters. I hope work didn’t consume you, even though you let your job get away from you in your thirties. I hope you gave your parents the stage and the time. I’m sure you’ve turned toward many humans, loved them, held them, and cared for them. But I hope you’ve done the same for yourself. Somehow, I know you will.

I want you to remember a few things about this time in your life. I want you to remember how light you felt when you rode Crow, that big chestnut horse you adored. I want you to remember how it felt to see your words in print for the first time, proof you exist. I want you to remember your little yard in front of your first home, the mow lines, and how much you care about grass and impressing the neighbors. I want you to remember late nights in the garage with Jake, refurbishing furniture so everything in your home always reminds you of the work, the polish. I want you to remember the smell of hot tomatoes and summer with your small niece and nephew. I want you to remember their sticky cheeks and bursting, tiny voices. Remember that Jake loves to build you things. Remember the ocean with your mom and sister, how it feels to reach out to them, and love them in the morning fog of Carmel. Remember the Northwoods with your friends when none of you had children. Remember hot, fried buttered buns at fish fries and how much time you had to watch your peonies grow. Remember the feverish wanting of pregnancy, the unknown hope of craving expansiveness, a physical outwardness. 

I also want you to remember the hard things. I want you to remember living paycheck to paycheck, not being able to get the things you wanted because you didn’t have enough money. I want you to remember the doctor bills you struggled to pay, crying on the way home from work, not being able to imagine traveling to other countries, and wondering if your life was limited to 200 miles north, east, south, and west of your home. Did you travel more? Do you still feel this?

All these things will feel different to you now, perhaps as distant memories. Small moments in your thirties that you’ll read later like you’re starving. Perhaps there’s something else entirely that makes you feel light. I hope you’re still riding. I can imagine you still care about clean yards and a pretty lawn. That’s what makes you a lot like your dad. We carry our family with us everywhere.

When you were in grade school, you’d write long lists of “favorite things” so you could look back years later and read about how much you’d changed. You were obsessed with seeing that, five years ago, you had a crush on so-and-so and loved (god forbid!) The O.C. and the color blue

All these things will feel different to you now, perhaps as distant memories. Small moments in your thirties that you’ll read later like you’re starving. Perhaps there’s something else entirely that makes you feel light.

Let’s try that again! Right now, I’m really into Brené Brown’s podcast (are podcasts still a thing?), Dirty Shirleys, antiquing, The Vermont Country Store catalog, my Gentle Reminder Calendar, Paper Mate colorful pens, watching Love Island (sorry, future me), dressing like Meryl Streep in It’s Complicated, sleep aids like sipping iced Sleepy Time Tea before bed, horse head bookends, weather patterns, gingham accents, and how Jake looks at me when I’m talking about something I love. Do you still love these things? Do you wish for them?

In my Passion Planner, I write down the biggest lesson I learn every month. Here’s what I’ve written this year:

  • Resonance is important.
  • Nothing beyond love and kindness matters.
  • Your anger is you. Not anyone else. Sit inside that.
  • Stop anticipating, trust the burn.
  • Being uncomfortable is progress.
  • Sadness is wide, grief is a close friend.
  • Nothing should be rushed.
  • You can always go back.
  • Hold fear and joy in equal glory. Both can exist at once.
  • You are always doing better than you think.
  • Dandelions are good.
  • To be happy, be more tree.
  • Don’t go to a concert high.

I’m sure you have so many to add now. Or maybe you don’t. Or maybe you think these are ridiculous. Or maybe you no longer find the need to make “lesson lists.”

I’m happy. I have my hard days. I have bad habits. I haven’t gone to the dentist to fill those cavities, so I hope you don’t have five crowns by now. I am putting a lot of money toward my 401K, so I hope I’m setting you up for success. I’m doing my best. That’s the lesson here. My thirty-something best is hopefully your sixty-something peace of mind. 

Will people find this article on the internet in twenty-five years? (Writer’s Note: Please don’t talk to me about how I’ll be sixty years old in twenty-five years.) Will they find it funny? Weird? I’m not sure. Perhaps, like in the past, internet articles will wash up like a lost bottle in the sea—little shards of the lived. And someday, I will come back to this past self, searching for my future. I might have to print it out, just in case.

Either way, I hope you’re happy too. I hope life feels full. I hope the people in your life reflect how you have shown your beacon of light in the world, no matter how faint or how strong. 


Brittany, your thirty-something (past) self

Lastly, I highly recommend you try this exercise.

Writing to a later version of myself gave me some specific clarity about who I want to be and how I want to grow. 

Here are some tips to try to write your own “future-self” letter:

  • Write down what you want to remember.
  • Write down what you don’t want to remember.
  • Write about your favorite things.
  • Jot down notes about how you’re feeling right now.
  • Scribble down the lessons you’ve learned.
  • Ask your future self how you’re different now.
  • Lastly, write a note to yourself in a year, three years, five years… put them in an envelope and write down the date you can read them again.

Will you write yours?

BY Brittany Chaffee - September 20, 2022

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September 21, 2022 4:51 am

amazing article.

Jessica Camerata
September 21, 2022 8:09 am

What an interesting thing to do I love this idea!

xo Jessica
<a href=”https://anindigoday.com/”>an indigo day</a>

September 21, 2022 10:00 am

This was absolutely beautiful – I did not expect to stumble across this this morning. Your writing is soft, and clever, and inspiring. You should be proud of what you created here. Thank you for sharing.

September 21, 2022 2:10 pm

This was absolutely beautiful. I didn’t expect to get emotional reading it but as a 36 year old woman so much of what you said was relatable. Thank you

Britney Head
April 7, 2023 5:07 am

Amazing article! Thanks for the positive and encouraging words of wisdom! 😊

April 7, 2023 9:00 am
Reply to  Britney Head

Thank you so much for reading, Britney! Have a lovely weekend!

April 20, 2023 2:29 am

Thank you for this. I am 70 and my 8 year old adopted daughter has an assignment to do this very thing. I think it will be a great experience for her. Your words reached my heart and came out of my eyes. Thank you

April 20, 2023 8:57 am
Reply to  Diane

Hello, Diane. It is so incredible to me that your daughter is doing this exercise! I think I did something like it at her age too and I wish I could find that letter now. Thank you for reading and loving.

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