A Letter to Oneself Encourages Self-Reflection

I recently heard about another interesting use of handwritten letters to encourage self-reflection. This one came from a visitor to my table at the Viroqua Book Fest in Wisconsin in April 2025. The gentleman who conveyed this story to me was a retired teacher who once worked in a New York City public school in an impoverished neighborhood.

At one point in his career, the teacher took part in a day-long retreat for teachers, a sort of self-care event for harried,overworked public servants. At the end of a day of exercises and activities, the retreat leader asked each participant to write a handwritten letter to themselves. Each person was given paper, pen, and envelope, and asked to express in the letter, any feelings, thoughts, or emotions that came up for them during, or at the end of the retreat.

Once each person finished writing, they were asked to place the letter in their envelope and address it to themselves at their home. Everyone did so. The retreat leader then asked each person to walk around the room and hand their letter to a total stranger in the group. Each person who accepted a letter was asked to put that unopened letter in the mail sometime over the upcoming three weeks. The letter’s arrival time was, therefore, unpredictable.  

The writers were told that when the letter arrived at their home, to reread it carefully and reflect on the thoughts and feelings they had experienced during or at the conclusion of the retreat. Did anything they had written at the retreat surprise them? Had anything changed in their thinking since then?

The teacher who spoke to me described what an amazing experience it was to reread what he had written down when not rushed, distracted, and stressed, as he often was when he was “on the job.”

I wonder how many times we all could benefit from taking a quiet pause, to think introspectively and express ourselves in cathartic words on paper. Rereading our own words weeks later might offer new insights, cement a weak commitment we’ve made to ourselves, or help to launch something new in our lives. That is the beauty of taking time to write down our authentic feelings on paper. Letters and journals are two perfect vehicles for doing this. 

If you are planning an event or retreat for your job, in your religious organization, or club, consider incorporating this interesting exercise for the participants. Who knows what impact it might have now or far into the future. This tale is yet another example of the ways in which handwritten letters can surprise, delight, improve, and support us in our day-to-day lives. So, please pick up that pen and you may just surprise yourself!