The Heart-Strong Friendship

A little over a year ago, I didn’t know Tremayne Seymour. Why would I? He’s currently incarcerated at a prison in Virginia. I live in Maine.

A painting changed that.

I was at the Returning Citizens Luncheon in Virginia, an event that honors people coming home from prison and the families who carry the weight with them. Part of it was a silent auction of artwork made by people who are currently incarcerated. One piece pulled me in. It was called “Mother Earth.” I placed a bid. I won.

I wanted to thank the artist and let them know that their work moved me. I found out I could reach them through a prison messaging app. So, I did.

It was Tremayne. He’s incarcerated at Lawrenceville Correctional Center in Virginia. He taught himself to paint on the inside, and he uses his art to work through anxiety he’s carried his whole life. He even built a program to help other men do the same.

That thank you note turned into a correspondence. The correspondence turned into a friendship. The friendship turned into an art show called FROM WITHIN¹, featuring paintings by incarcerated artists. And now it’s turning into a book.

Side note. If you want the full story on the start of our friendship, check out: “A Friendship That Started With a Painting.”²

Tremayne and I are writing a children’s book together. It’s called The Heart-Strong Friendship. I wrote the story and Tremayne is painting the scenes for it.

At its heart, it’s built on a question.

What happens when a white guy from Maine who went to Bowdoin College and a Black man from Brooklyn who went to prison decide to create something together?

Some of the most beautiful friendships grow between people from completely different worlds. Ours is one of them.

The book tells that story, with a twist. We’re not our adult selves in it. We put ourselves back into the worlds we lived in at seven years old. And we imagine what would have happened if we’d somehow met back then.

Little Tremayne lives in Bed-Stuy, Brooklyn. He loves to draw, and his sketchbook goes everywhere he goes. Little Jeremy lives in the woods of Maine. He loves to explore and build. And they both love trees. One of them gets to see trees once a week, at the park with his grandmother. The other has them in every direction, all day long. Same love. Opposite amounts. A lost sketchbook brings the two boys together, and a friendship grows through letters.

It’s a story about what two people can build together when they don’t let difference keep them apart.

And HOW we’re making it is part of the story too.

Making a book with someone in prison is hard in ways I never expected.

Most of our back and forth happens in short chats through a prison messaging app. We can also talk by phone and do video visits. But I’m in Maine and he’s in Virginia, so in-person visits are hard to pull off. A lot of the artwork he shows me, I see over a screen. When he holds up a character sketch on a video visit, I take a picture of the screen so I can study the details later. That’s how I first saw Little Tremayne and Little Jeremy. Concepts he drew, held to a camera, saved as a picture I took of a video call.

A photo of a screen with Tremayne showing his initial concept sketches of Little Tremayne and Jeremy.

Or that’s how we used to do it. A few weeks ago, Tremayne lost his video privileges for a month. It turns out my taking those pictures wasn’t allowed. There was no warning. We had to figure out a new way to review his art, which slows everything down again.

Not only are we working across literal walls, but there are also figurative ones as well. Neither of us has done this before. This is one of my first children’s books. I’m working on another one as well. And it’s Tremayne’s first time illustrating one. So, we’re teaching ourselves as we go. I pass along process documents I get from professional illustrators, and we figure out the rest together.

And then there’s developing the manuscript.

I can’t email it to him. I have to mail it. There’s a workaround I’ve found, but it’s not ideal. I turn each page of a PDF into a JPEG and send the pages as images so he can read them on his tablet. Each image costs 20 cents. That adds up fast when you’re drafting something together.

Mailing it isn’t a big deal on its own. It takes about a week to reach Virginia, and then it has to be approved.

But it’s not always smooth. This summer, I sent Tremayne three things. An updated manuscript. A printout of an email from Maine Inside Out. A printout of an email from ArtVan promoting FROM WITHIN. Each one was 5 pages, front and back. That’s the most I could send at a time.

A week later he told me they’d been rejected. He didn’t know why.

Then they showed up back in my mailbox. I opened the envelope. It said they’d exceeded the limit of 3 pages, front and back.

The notice that came back with my returned envelopes. It says my mail went over a 3-page limit. I’d been sending 5 pages for months without a problem.

I’ve sent plenty of 5-page envelopes before. The limit used to be 5. It quietly became 3, and nobody told anyone. The rule changed, the reason is anyone’s guess, and it never got communicated down.

To resend the draft, I had to send it in 4 different mailings to stay under the 3-page limit. Any one of those envelopes could get rejected, so we didn’t really know when he’d have the full manuscript in hand to keep illustrating.

And this is just me sending a manuscript. But what if it had been a letter from his daughter? Drawings from his granddaughter? Same rejection. Same delay.

And it isn’t just paper. A while back, I bought a set of professional paintbrushes and donated them to Colorful Transformations, the art program Tremayne runs inside. A small set, but the good kind, the sort you need for fine detail work. About a hundred dollars’ worth. We did it the right way. Tremayne got clearance ahead of time, and we went through all the proper channels. Then the administration at Lawrenceville changed. The 3 most senior positions changed. And with that change, the brushes were rejected. No reason we could get. Maybe they went back to the seller. Maybe they’re just gone. Either way, a gift meant to help men heal through art never made it inside.

These are small things on their own. A paper cut here. A paper cut there. But it’s death by a thousand of them. And it makes me wonder how we expect people to heal when they’re taking these little cuts day after day, each one making it harder to stay strong.

For another book I’m writing, I’m working with a professional illustrator in France. She’s much farther away than Tremayne. And working with her is effortless. She emails me a sketch in seconds. We exchange messages at no cost.

The distance that makes this hard isn’t miles. It’s the walls.

So, why do it the hard way?

I could hire a professional illustrator. Someone who could email me files and turn things around fast. The book would come together quicker and smoother.

But I came across an idea a while back. I think it was from the Daily Stoic, though I honestly can’t remember. I think about it a lot. Some people DO hard things because they’re hard. And some people DON’T do hard things, because they’re hard.

I’ve always been the first kind. I don’t fully know why. It’s just how I’m built. Why run a 5k when you can run a marathon? Why alpine ski when you can telemark? Why pick up surfing at 40 when your strength and agility aren’t what they used to be?

Because they’re hard. And because what I learn about myself along the way is always worth more than any result or success I might have.

And so, I look at it this way. Love is doing hard things because they’re hard. Fear is not doing hard things because they’re hard.

The fear-based way to make this book is to hand it to a pro and get out of the way. The love-based way is to make it side by side with Tremayne. Because it’s our story. Two guys who honestly don’t know what we’re doing, figuring it out one paper cut at a time.

The book will be better for it. I really believe that. But that’s not even the main thing.

The last lines of the book are about how the most beautiful thing the two boys build isn’t the art show they dream up together. It’s their friendship.

That’s true for us too. Every rejected envelope. Every photo of a screen. Every 20-cent JPEG. I can feel our friendship getting deeper through all of it. The book is what we’re making. The friendship is what we’re building.

This past Sunday, I led the service at the Unitarian Universalist Church of Brunswick. It was built around our story, and my reflection was called “The Art of Falling Forward.” It was also the first public reading of The Heart-Strong Friendship. I read it during the Time for All Ages, the part of the service where a children’s book is read to the kids. The book is far from finished. What people saw were concept sketches, photos from our video calls, and scenes that are still coming together.

I was certainly nervous reading the story. But introducing it to others made it feel even more real. And the comments I received validated what I believe. We need more stories like this in the world.

If you’d like to watch or listen, you can find the service here:

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This Substack is a production of Heart-Strong, a nonprofit centered around a simple belief. The world works better, for everyone and everything in it, when more of us are pulled by love than controlled by fear. We have an open invite for anyone curious about what that world could look like. Learn more at www.heart-strong.org.

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