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Gratitude Letters: A 2021 Experiment in Radical Appreciation

Looking back, I have this to regret, that too often when I loved, I did not say so.

—Ray Stannard Baker

I spent this time last year—like so many of you—in thoughtful reflection of where I have been and where I was going. I thought about resolutions and goals and big dreams. One thing I kept coming back to was the SMART side of goals. (Specific, Measurable, Achievable, Relevant, and Timely.) Be more grateful is something I heard folks in my life sharing as a priority and I began to think about tangible things that support a resolution like that. That’s how my year of Gratitude Letters was born.

The task was to write 52 letters (one every week) to 52 people who had made a positive impact on my life. Not on their birthday. Not because they’d just started a new job. Not for any specific holiday or reason. But rather because I was thinking of them. Because I was grateful for them. Because when you live with gratitude first, everyone wins.

First, I gathered my materials. I ordered blank cards and envelopes from Earth Hero. I was really mindful about purchasing sustainably manufactured cards on recycled paper. The cards are made in the United States and are carbon neutral. The stationery was a tad more autumnal than I initially realized… but that only meant I was extra excited for the fall letters. I also bought stamps. At the time, forever stamps were $0.55. That upfront postage investment was just under $30. Not bad for a year worth of letters. I found having all my materials readily available from day one made the project an easy, accessible activity.

Next, I made a numbered list of 52 people who profoundly impacted my life. In my case, I chose to write to 52 people who are living and who I could easily send a physical card to. I imagine this project could be impactful if an occasional letter was written to someone no longer with us. As an aside, I recognize you might pause for a second at this—52 people! It seems like a high number, perhaps, until you start writing. To jumpstart your brain, consider these “categories” of people: family members, colleagues, school friends, roommates, people you’ve volunteered with, people you’ve worshiped with, past teachers or mentors or coaches, etc. I’ll also share that as the year progressed, there were so many times I realized I should have included so many other people. It’s a choice to see the world as friendly and beautiful and loving and kind. But for the purposes of this project, I decided to honor the original 52 people I listed in December 2020.

With my pre-work done, I realized all I had to do to make this goal achievable was schedule intentional time to make it so. I decided Sunday would be my letter writing day. Each Sunday, I used a random number generator, 1 – 52. Whoever the generator chose was my person for that week. Rather than sit with the name or feel weird or uncomfortable about writing a letter out of nowhere—remembering that some of these folks aren’t people I talk to on a necessarily regular basis—I would immediately write.

And here’s what I found delightfully challenging. I knew from day one I didn’t want to tell anyone about this. I wanted it to be the kind of thing that shows up in your mailbox when you’re least expecting it and brings you a spark of joy. I also didn’t want it to seem like another Smile Project initiative or experiment. And so, even though there were times I wanted to explain what I was doing so my random card made sense, I refrained. They were always just posed as “thinking of you,” “just because,” “I want you to know how grateful I am for you” cards.

Each Monday morning, snow, rain, sun, or hail, I would traipse to the mailbox to send my little card into the world. Today, I will send my 52nd letter. In the course of one year, I’ve mailed to 3 countries and 18 U.S. states from Hawaii and Washington to New Mexico and New Jersey. Northern Ireland to Mexico. Sprinkling my heart everywhere in between. I’ve mailed to 52 people who I hope maybe now have a small idea of how much I love and appreciate them.

And the thing about sending cards? It’s a gift that keeps on giving. Depending on the location of the recipient, I could almost always expect a text of gratitude and appreciation by Thursday. I received several letters and a postcard back. The correspondence led to Zoom catch up dates and phone calls. It was an old fashioned way of saying hello… of starting a conversation from miles apart. Some of the people I wrote to I haven’t seen in years.

Because I knew I would want to share this project with the wider Smile Project community, I had an extra step of journaling throughout the process. I’d like to share a few of my early, unedited reflections:

January 3, 2021 Reflection

I wrote the letter and my heart soared. I talked about a couple of our shared memories. I thanked her for being a good friend. It’s such a freeing way to write—not with any real purpose if you will. But just to write because you have something to say. Because it matters. I’m feeling really good about this all already. Gratitude. It matters.

January 10, 2021 Reflection

One thing I’ve found often with projects like this is that even when you do something “randomly” you somehow end up with exactly what you’re supposed to end up with. I am beginning to have this idea that if we just trust the process, we’ll get what we need to get.

January 24, 2021 Reflection

I find the ritual of picking the name to be perhaps the most endearing part of this entire project. All week I wonder who it will land on, and today, as I pressed the random number generator, I even thought about the order in which I put the people on the list originally. The very first name I wrote could well be the last name I pull. And yet I choose to believe that folks are receiving their letter exactly when they need to.

I got a response from last week’s letter. They said it arrived at the perfect time. There is something to this. Almost a “whatever happens is what should happen” thing. Trusting in the universe.

January 31, 2021 Reflection

It always lands where it’s supposed to.

February 14, 2021 Reflection

I was thinking about how when I was drawing the name I almost hoped it wouldn’t be someone who would think it was weird. Then I wondered who on my list would think something like this was weird and also why they would think something like this is weird. And also why we live in a society where people think expressing love and gratitude with no ulterior motive or reason is weird.

December 12, 2021 Reflection

I cannot believe that my last two names are going to be my brother and sister-in-law at some point the next two weeks.

I have a document on my computer. A Year of Gratitude. It’s where my list of 52 lives and how I kept track of who had or hadn’t been written to yet. It’s also where I journaled the above reflections and responses from folks. As I sat down this morning to write this full post, I found myself re-reading the responses I received from people and realized the real kicker of this project. I wrote 52 cards. But I got the biggest return.

Every reconnection. Every eye-opening conversation. Every vulnerable moment of, “hey it’s been a while but I love you and appreciate how you have changed my life for the better.” Every text for an address. Every stamp, every card. How lucky I am to have people who shake up my world and how lucky I am to be able to remind them how loved they are.

Love always,



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