The best thing you can do with what you have

On a glass bottom boat in Anguilla, I watched a dream come true. I'm still sitting with what it means.

There are a lot of things you can do with your money. Most of them are things you eventually stop noticing. The car, the house, the trip that looks right in a photo. Those things mattered to an earlier version of me. I chased them. I got them. I know exactly what they feel like from the inside.

What I was watching from a beach in Anguilla last month was different.

I was watching a dream actually happen. And I was aware, in real time, with my wife beside me, that this was one of the best moments of my life. Not because of what I had. Because of what I had made possible for someone else.

From left to right: Eric Greitens, Judy Henderson, Junior, Judd

HOW WE GOT HERE

A little over a year ago, I was at a book launch in New York for a woman named Judy Henderson. Her book is called When the Light Finds Us. Judy was wrongly convicted of a murder she did not commit and sentenced to 50 years without parole. She served 36 of them.

While Judy was inside, her daughter Angel got married on a beach in Anguilla. Judy wasn’t there.

I invited Judy and Angel on my podcast, Behind the Armor. I wanted to understand what it means to mother from behind a wall. How incarceration separates parents from their children in ways that don’t end when the sentence does.

Hearing Judy’s story moved me in ways I couldn’t name at the time. So I decided to tell it fully. I spent months on it. I flew to Missouri to meet her attorneys. I sat down with Eric Greitens, the former governor who pardoned her. I went deeper with Judy and with Angel. The whole arc became Season 3 of Behind the Armor.

After the podcast, I kept thinking about something Judy had told me. She had made a vision board in prison. On it she had written: a full pardon. Her freedom. Her family. And one more thing. A glass bottom boat in Anguilla.

I knew we were going to complete it.

THE BOAT

On a Friday morning last month, Judy boarded a glass bottom boat captained by a man named Junior. He has run that boat for 33 years. He talked about the love and intention he has put into it across those decades. The care, the pride, the people he has carried out to sea.

Judy cannot swim. She had never been in the ocean.

Eric, a former Navy SEAL, went in first. He guided her in slowly. And somewhere beneath the surface of the Caribbean, she looked down through her snorkel mask and saw sea turtles moving through the water below her.

I was standing on the beach watching it happen.

There are a lot of things you can do with your money. But making a dream actually happen, and being present enough to watch it. That is something else entirely.

Over lunch, Angel turned to her husband David and asked quietly: do you think there’s another Junior on the island?

Something about the boat felt familiar. The name. The hull. The way it was painted.

Twenty years ago, Angel and David got married in Anguilla. They had gone out on a glass bottom boat that day. Junior’s boat. The same one.

Judy had not been there for the wedding. She was in prison.

And now here she was. Free. In the water. With her daughter beside her. On the same boat, on the same water, twenty years later.

Junior has been running that boat for 33 years. He had no way of knowing what he was carrying that day. What his boat had held across two decades without anyone knowing it. What it meant that it was still there, and that we had found it.

I don’t believe that was a coincidence.

Junior and Judy

WHAT I’M SITTING WITH

Judy held that vision board in prison for years. Not desperately. With a kind of patient, unshakeable faith that I find hard to fully describe. She never stopped seeing the glass bottom boat. Even when there was no logical reason to believe she would ever be on one.

And one Friday morning in Anguilla, she was.

Hope isn’t naive. It may be the most disciplined thing you can practice.

I came home and I’ve been thinking about that beach moment ever since. The one where I turned to my wife and said: this is the best thing I’ve done with what I have.

The earlier version of me measured a good use of resources by what I could show for it. The version I’m becoming measures it by what I can make possible for someone else.

What’s the best thing you could do with what you already have?

Hit reply and tell me. I’d love to know what you’re sitting with.

— Judd