A Letter to Your Younger Self: Free Journaling Prompts

Dolores Pfeuffer-Scherer
3 min readFeb 14, 2024

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Photo by Sixteen Miles Out on Unsplash

As we celebrate Valentine’s Day, I urge you to write a heartfelt letter to your younger self. Take some time to answer the following prompts and recall the younger version of yourself and your life’s journey to get to where you are today. Be honest and allow yourself the opportunity to feel and re-feel all the events you discuss. This is not an easy exercise, but very meaningful.

Thank you for participating in this journaling exercise with me; know that I am always wishing you the best, from my heart to yours.

Journaling Prompts:

*What is the main point you want to convey to your younger self? For example, in my case, it is reassurance. Think about the most important thing you would tell yourself and write it in the first sentence. (Don’t worry about grammar, just write! And if you are walking through a difficult season, it is okay to share that too.)

*What can you share with yourself about your successes, adventures, accomplishments, and all the good things or “wins” that you never fully anticipated? Did you go to school? What are your professional accomplishments? Do you have a family? What about your friends? How do you impact the lives of others around you in the best ways? Are you a force for good in your circle and what does that look like? What have you worked hard for that panned out and where and what are your unanticipated joys? (Please think hard and be honest because you likely positively impact people all the time, we just don’t give it much thought.)

*What about the hard things you have been through? Beyond terrible events, such as loss, grief, and all the things that nearly break us apart, what would you say to your younger self to provide reassurance while being honest? How can you provide the tools and advice to yourself, knowing what the future holds? And what lessons did you learn from such experiences were you able to rise above it and how did you come out of it? (If you are still working your way through these things, acknowledge that.)

One example in my case was placing my trust in people who simply did not deserve it. Believing in people who were not worthy of me, thinking that I knew the good, real person inside of them. I could have saved myself a great deal of heartbreak with that knowledge. And yet, in writing this letter I also realized that I would rather be the person who believes in others versus the person who is less than kind. That is somewhat of a positive out of the negatives.

*If you can, talk about the hard things, such as loss. Allow yourself to cry, if necessary, and remind yourself about the people who were important to you in that they impacted you deeply, and how you miss them. (If you can’t do this if your grief is still too raw, skip this, please.)

*Talk a little about your mistakes and forgive yourself for each and every one. You did the best you could at the time, no doubt, and you need to let go of what you see as your failures, missteps, etc. Tell your younger self to be more forgiving with these things and remind yourself that we all are human.

*Finally, what is your big takeaway that you want to share? Perhaps it is that you are loved. Maybe it is that you are a survivor and you keep rising. My wish for you is that you celebrate who you are at this moment: flawed, complex, and beautiful.

In other words, you are human. And that, my friend, is certainly something to celebrate.

Happy Valentine’s Day to who we are in the present and a toast to our younger selves.

Photo by Enis Yavuz on Unsplash

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Dolores Pfeuffer-Scherer

Writer. Christian. Chronically ill, yet joyful. History nerd. Adopter of shelter pets. I can only function with hot tea. I love cake. I mean really love cake.