Track 1
Three-Toothed Freedom
April 29, 2026
So I’m walking down Main Street.
I came here a month ago, after my addictions course completed. I just wanted to understand the people on the street a little better. You can’t learn that from a book. You’ve got to go down there. In the street.
Downtown east side of Vancouver. There’s a street called Hastings. Hastings and Main is where all the action is. That’s where I saw it.
The biggest smile humanly possible on a man who I think only had three teeth.
I had to ask. “What are you smiling about?”
“Freedom, man. Freedom.”
That’s what he said. And he wasn’t lying.
I could see what he had. I could see what he didn’t have. The man was missing a shoe. And the sock. But what he did have was something that took me 50 years to get.
Freedom.
Now I’m not saying the right choice is to give up all your earthly possessions and go sit on a sidewalk and live in the streets. What I’m saying is he found a way to be free of whatever happened to him, whoever happened to him, to make his best choice. To get freedom. To live on the street.
I saw his foot. There’s no way that’s a positive life choice. But I also saw the biggest three-tooth smile I can ever imagine. He had that. That was his freedom. And that may be the only thing he has.
I doubt he has a wallet. He had a meager box. A few items. And somehow they always seem to have Doritos. Which must be the official sponsor of the downtown east side.
But that man had freedom.
He might have it more than I’ll ever have it, in a certain point of view. And that’s something. And he was proud of it. And that’s something too.
I just wanted to think about that for a minute.
Two Beers with Leo
✱1 Recent studies suggest people living on the street often describe a kind of freedom the rest of us don’t have. They say mainstream life feels boring and rule-bound. They say their lives feel more their own. ✱2 Other research suggests there’s a real difference between how someone becomes homeless and why they stay. The first is rarely a choice. The second often is. People sometimes pick the sidewalk over the system because the sidewalk leaves them more room to be themselves. And in a Canadian study where homeless people were asked what mattered most to them, the word that came up first wasn’t housing. It was choices.
For full sources and citations, see The Research Trail at themensdateproject.org/research
—Leo
Ruby’s Woowoo
Here’s what he was teaching, whether he knew it or not. Freedom isn’t the absence of hard things. It’s the absence of pretending the hard things shouldn’t be happening to you.
He had a missing shoe. He had a missing sock. He wasn’t fighting either one. He wasn’t waiting for the shoe to come back so he could finally start smiling. The smile was already there. The smile was the choice he’d already made.
Most of us are walking around with both shoes on, waiting. Waiting for the right job, the right partner, the right body, the right bank account, the right parents we never got, the right apology that’s never going to come. We’ve decided we’ll be free once those things sort themselves out. And until then, we’re not. We’re holding the door shut on our own freedom and waiting for someone else to open it from the outside.
He didn’t do that. Whatever happened to him, whoever happened to him, at some point he stopped waiting. He sat down on a sidewalk on Hastings and Main, and he found a way to be free of it. Not free of the consequences. Free of the story that the consequences got to decide who he was.
That’s the lesson and it’s free for everybody. The choice was never about the shoe. The choice was never about the housing or the wallet or the teeth. The choice is whether you keep handing your freedom over to the thing that hurt you, or whether you take it back.
He took it back. On a sidewalk. With three teeth. With Doritos.
If a man with one shoe and no sock can find freedom, the rest of us......with both shoes on, with houses, with wallets, with the whole fit-out......have no excuse. We’ve just got better hiding places for our cages.
—Ruby
Daisy’s Juice Box
The juice is this: He didn’t earn it. You did.
That’s the thing. That’s the whole thing. He didn’t go to therapy. He didn’t read the books. He didn’t sit through fifty years of trying to be a good son, a good father, a good husband, a good friend. He didn’t bury the people you buried. He didn’t do the work. And he got there first.
That should make you angry. It doesn’t. That’s the squeeze.
Because somewhere in you, you already know......the work wasn’t what got you there. The work just got you to the door. The freedom was always free. He was just willing to pick it up off the sidewalk while the rest of us were still trying to deserve it.
You spent fifty years trying to earn what he was sitting in. And the second you saw him, you didn’t envy him......you recognized him.
That’s not pity. That’s not even compassion. That’s a man on a sidewalk and a man walking past, and for one second they’re the same height. That’s the juice.
Freedom isn’t a reward for suffering. It’s a decision you can make at any age, on any sidewalk, with any number of teeth. He just made it sooner.
—Daisy