A Friendship That Started With a Painting

Last September, I found myself at the Returning Citizens Luncheon in Virginia. It’s an annual gathering that honors returning citizens and families who are system impacted. I wrote about that experience in an earlier piece called “There’s Room on the Porch for Everyone.”

Part of the event was a silent auction featuring artwork created by people who are currently incarcerated. One painting stopped me. It was called “Mother Earth.”

The first thing I noticed was the technical skill. Whoever made this knew what they were doing. But the longer I looked, the more I discovered. New details kept revealing themselves. Layers of meaning I hadn’t seen at first glance. It was the kind of work that rewards attention.

I placed a bid. I won.

When I got home and hung the painting, I wanted to reach out to the artist. Not to ask for anything. Just to thank them. To let them know that someone on the outside saw their work and was moved by it.

I found out I could contact them through JPay, a prison communication app. So, I did. I told him his painting was now hanging in my home in Maine. That I was grateful for the beauty he’d put into the world.

He wrote back.

His name is Tremayne. And that first exchange started a correspondence that has slowly grown into something I’d call a friendship.

Messages Through the Wall

There’s something strange and beautiful about getting to know someone through short messages sent through a prison communication system. You can’t rush it. You can’t hop on a call whenever you want. Each message costs money. More on that in my next piece.

Over the last few months, we shared pieces of our lives. He learned about my Heart-Strong Adventure. I learned about his journey, his art, his hopes for what comes after.

What I didn’t know was where he was incarcerated. I didn’t ask, and it hadn’t come up.

The Meeting

When my friend Sam invited me to visit Lawrenceville Correctional Center in December, I mentioned it to Tremayne in one of our messages. He asked which program I was visiting. When I told him, he said he’d try to come.

After the I OWE MORE session ended, a man walked up to me. “I made it,” he said.

It was Tremayne.

We talked for close to 30 minutes. And in that conversation, I learned things I hadn’t known from our messages.

The Anxiety He Carries

Tremayne told me he’s struggled with crippling anxiety his whole life. The kind that used to make him pass out. I tried to imagine carrying that inside a prison. The constant alertness. The noise. The lack of control. Fear on top of fear.

But here’s what struck me most. Tremayne didn’t let that anxiety define him. He found a way through it. He taught himself to paint. And how to use his painting to help him with his anxiety. He then turned around and built something to help others do the same.

Colorful Transformations

Tremayne created a 12-week program inside Lawrenceville called Colorful Transformations. It teaches men how to use art to deal with anxiety, stress, and depression. It’s based on the eight stages of psychosocial development. He’s already run three sessions, with a fourth starting soon.

He found his purpose inside those walls.

When he talked about his plans for when he gets out, his whole presence shifted. He wants to work with young people through art. Help them find what he found. Watching him describe it, I could see how his gentle spirit would be exactly what struggling kids need.

This is a pattern I keep seeing. Someone does the work to free themselves from fear. They build community. They create space for vulnerability and healing. And then they extend it outward. Sam did it with I OWE MORE. Tremayne is doing it with Colorful Transformations.

Healing doesn’t stay contained. It spills over.

What’s Unfolding

Since that visit, Tremayne and I have been talking about what else might be possible. We’re in the early stages of exploring an art show and fundraiser featuring work from incarcerated artists. A way to bring their beauty to more people on the outside. A way for them to feel seen.

It’s still very much in development. But something is taking shape.

Stay tuned.

What This Friendship Is Teaching Me

I reached out to Tremayne because I wanted him to feel seen and appreciated. I wanted him to know that people on the outside are thinking about those on the inside.

What I didn’t expect was how much I would receive in return.

Tremayne has shown me what it looks like to transform suffering into service. To take the hardest thing you carry and turn it into something that helps others. He’s doing some very meaningful work, and he’s doing it from inside a prison.

This friendship started with a painting. I don’t know where it’s going. But I’m grateful it exists.

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This is the third piece in a short series. Next, I’ll explore what it actually costs to stay connected to the people you love when you’re behind bars.