I’m in the letter-writing business.
From 2018 through 2023, I attempted (and succeeded) in writing at least 100 physical letters every year.
Since 2023, I’ve increased my goal to 150, and for the past two years, I’ve also succeeded in meeting and exceeding it.
Last year, I wrote 222 letters, and this year, I’ve already written 159 letters.
I’ve written more than 700 letters over the past five years to a variety of people:
Students and former students. The parents of students and former students. My former teachers, professors, and bosses. My children’s principals and teachers. My wife and kids. My father. Friends. Colleagues. Clients. Business owners. Storytellers. Authors. Servers. Politicians.
Responses to readers and storytelling fans who send me letters.
More than 95% of my letters are written in the spirit of kindness and enthusiasm, designed to convey information or express a positive message.
Occasionally, I write a letter for other reasons. When I do, it’s usually a letter directed at an unethical politician, a business that has done me wrong, or an administrator who is making decisions without a fundamental understanding of the issues at hand or is too lazy to take action.
I like writing those letters, too. I also have a pile of small, envelope-sized pride flags that I send to bigots along with my letters.
This makes me especially happy.
Why do I do all this?
I think Albus Dumbledore said it best:
“Words are, in my not-so-humble opinion, our most inexhaustible source of magic, capable of both influencing injury and remedying it.”
That’s it.
I write letters because they make the recipients feel good and often strengthen our relationship. Writing to someone takes time and effort. Addressing an envelope and affixing a stamp are things that many of us no longer do. Receiving an actual letter in the mail is both surprising and appreciated.
Also, writing letters has produced remarkable results.
Thanks to writing letters, I’ve reconnected with some amazing people:
At least four former teachers,
Two former principals
Half a dozen former college professors
Two former bosses
An endless number of former students
I exchange letters with many of these people regularly.
I also managed to reconnect with two former teachers, less than a year before they passed away. I let each one know how much they meant to me and continue to mean to me today.
I feel so lucky to have sent those letters before their passing.
And while these ongoing connections mean a great deal to me, it turns out that they might mean even more to the recipients of my letters.
New research suggests that casually reaching out to people in our social circles means more than we realize.
“Even sending a brief message reaching out to check in on someone, just to say ‘Hi,’ that you are thinking of them, and to ask how they’re doing, can be appreciated more than people think,” said Peggy Liu, an associate professor of business administration with the University of Pittsburgh Katz Graduate School of Business.
Dr. Liu is the lead author of a new study — published in the Journal of Personality and Social Psychology — that found people tend to underestimate how much friends like hearing from them.
The more surprising the check-in (from those who hadn’t been in contact recently) tended to be especially powerful.
Physical letters arriving in a mailbox, I suspect, might be the most surprising of all.
Dr. Liu noted that many people feel awkward about reaching out due to a phenomenon known as the “liking gap,” or the tendency to underestimate how well-liked we really are.
People may also hold themselves back due to a phenomenon known as the “beautiful mess effect,” which suggests that when we are vulnerable with others, we worry we will be judged harshly.
According to the study, this kind of negativity bias tends to permeate all aspects of friendship and can have a tangible impact on how we behave and interact.
In writing as many letters for as long as I have, I’ve discovered one absolute certainty:
Except for the critical and angry letters I rarely write, no one is ever upset or confused about receiving a letter from me. They are universally happy, excited, pleased, and grateful.
“The liking gap” isn’t a bias that has thankfully never plagued me. I start with the assumption that a person will like me if they get to know me, and I assume I can almost always win them over through kindness, wit, and a willingness to extend myself.
And the beautiful mess effect?
Forget it.
I’ve been sharing stories about me and my past for years — really vulnerable moments of embarrassment, failure, stupidity, and shame — and every time I do, people don’t judge me.
They grow closer to me.
My suggestion:
Write a letter today. It need not be long or elaborate. Write a simple expression of friendship, appreciation, or love to someone not expecting it, and drop that letter in the mail.
It will likely mean the world to the recipient, which is a beautiful thing, but it may also result in something beautiful for you, too:
A new friend.
A stronger friendship.
A timely message to someone whose time might be running out.
Go ahead. Write something today.
I can’t recommend it enough.
