The Probability Math of an Optimist

Some of you know me well. Some of you know me a little. And a lot of you only know me through what I’ve written here. That’s all you’ve got.

Which means you may not know this particular thing about me.

I am an extreme optimist.

Not the quiet, measured kind. The kind with my own math system.

Here’s how it works. When I want something to happen, I identify all the possible outcomes. Then I assign each one equal probability. Doesn’t matter how likely any of them actually are. If there are three outcomes, I have a one in three chance. Four outcomes, one in four. Simple. Clean. Airtight.

My wife Becca thinks my math is suspect.

I think it’s brilliant.

She’s been living with this system for a while now, so she has opinions. But I want to tell you a story about a specific calculation. One where I started with one in three odds, took a beach walk in Costa Rica, and ended up at 60-40. In the span of about forty-five minutes.

That’s not delusion. That’s just good math.

It started with Matthew McConaughey.

Becca and I have a Friday or Saturday night ritual. For a little over a year now, we’ve been watching Lyrics of Livin’ with Matthew McConaughey. If you don’t know it, look it up. It’s fantastic. We got deep into his movies around the same time. The Beach Bum. Dazed and Confused. The whole catalog. At a certain point, it stopped feeling like watching movies and started feeling like catching up with a guy we kind of know.

Which is, I realize, exactly the kind of thinking that leads to sending unsolicited emails.

But I’m getting ahead of myself.

The Idea

Somewhere in the middle of all that McConaughey immersion, an idea started forming.

What if two of his most iconic characters were the same person?

Wooderson from Dazed and Confused and Moondog from The Beach Bum. On the surface, they look like completely different guys. Wooderson is the charming, cool-as-hell dude who hangs around high school parties a little too long. Easy to write him off as a lovable slacker. But look closer. He’s wearing a Bob Marley shirt. He’s the one who steps in to break up the fight. He’s genuinely kind to everyone around him. There’s something real underneath the vibe.

And then there’s Moondog. A broken, brilliant poet adrift in the Florida Keys. Funny and free on the surface, but carrying something heavy underneath. A man whose charm has curdled into avoidance. Whose so-called freedom is really just a long drift away from anything real.

My idea was this: what if Wooderson’s effortless cool was never really freedom? What if it was avoidance? A young man moving through the world on charm alone, sidestepping anything that required him to actually show up. And what if Moondog is just what that looks like decades later, when the mask finally cracks?

It’s basically what Cobra Kai did with Johnny Lawrence. You take a character people wrote off as a one-dimensional jerk, give him a whole interior life, and suddenly you understand him. You don’t just watch him. You recognize him.

The deeper story is about a man learning to find his way back to presence, purpose, and emotional truth. That’s a Heart-Strong story if I’ve ever heard one.

Becca loved the idea too. But we never did anything with it other than let it sit in our imaginations. As Stephen King said, if an idea is a good one, it will keep coming back.

The Email

Almost a year went by.

Then one Friday night, Matthew did a Lyrics of Livin’ called “Make Love Stories.” It planted the idea for a love story in my head.

He told the story of a summer when he was a kid in Longview, Texas. Barefoot and shirtless in a shammy, sneaking into a lumberyard in the middle of the night to steal lumber. Not for profit. Not on a dare. To build a thirteen-story tree house in the piney woods near his house.

He said love stories are everywhere. Romances with ideas, with places, with the work that lights you up. That a barefoot kid giving himself completely to something beautiful, something no one asked him to build, that’s love. Not just a feeling. It’s a way of moving through the world.

I couldn’t help but think, that is certainly a Heart-Strong Adventure minus the whole stealing lumber thing.

And right then I thought, you know what? Fuck it. I’m going to email him.

Here’s what I wrote:

What’s up Matthew,

Spot on this is a love story! Not because there was a romance. Because a barefoot kid in a shammy chose something that lit him up, gave himself to it completely, and built something beautiful that no one asked him to build. That’s love. Not just a feeling. It’s a way we move through the world.

I’ve spent the past year exploring that exact idea through something called my Heart-Strong Adventure. It’s a yearlong journey exploring where love and fear show up in our world, especially in the lives of men. I write about it on Substack and host a podcast called Campfire Conversations, where I sit with people around actual fires and we talk about what it means to move from fear toward love.

I want to share something with you that your work has inspired. For over a year, an idea has been playing in my head called Wooderson to Moondog. The premise: those two characters are the same man, decades apart. Wooderson’s effortless charm was never just charm. It was avoidance. What looked like freedom was a young man tapped by fear and drifting from anything real. His relationships fell apart. His mask cracked. And decades later, a broken-but-brilliant poet washed up in the Florida Keys, trying to find his way back to presence, purpose, and emotional truth through creativity. I just wanted to share this idea with you because it came from our parallel journeys and explorations.

Now here’s the shot in the dark. I’ll be in Austin in early April. If you’d be open to sitting by a fire and having a conversation about love, fear, and what it means to be a man right now, I’d be honored to host you on Campfire Conversations. No script. No agenda. Just presence and honesty. Total long shot. But I figure, take a chance on love, right?

With respect and gratitude,

Jeremy Litchfield

Then I closed my laptop and sort of forgot about it. About a week later, after watching the next Lyrics of Livin’, I told Becca that I had emailed him.

And this is where the story turns to math. The math of an extreme optimist.

The Math

So I told Becca I had emailed Matthew McConaughey.

She looked at me the way she always looks at me when I’ve done something that makes complete sense to me and zero sense to anyone else.

So I explained, if I send that email, I see that one of three things can happen.

· One, it never reaches him. Lost in the void. No harm, no foul, I never know.

· Two, it reaches him, he thinks it’s the stupidest thing he’s ever read, and I never hear about it.

· Three, it reaches him, he loves it, says yes, and we end up sitting by a fire in Austin talking about love, fear, and what it means to be a man. After which we obviously have dinner to talk about making Wooderson to Moondog.

Three possible outcomes. One of them leads to a campfire and dinner with Matthew McConaughey.

That’s a one in three chance!

Becca probably had different thoughts.

I want to be clear that her math and my math are very different systems. Hers involves something called actual probability. Mine involves something called optimism. We’ve agreed to disagree on which one is more useful.

But even I had to admit, one in three felt like it had some room for improvement. I wanted my odds to be more like 50-50.

Good thing we were about to head out on a beach walk in Costa Rica.

The Beach Walk

Becca and I headed out for a sunset walk on the beach. The kind of walk where the air is warm and your brain just starts wandering.

And somewhere between the waves and the last of the daylight, it hit me.

I had missed a fourth scenario!

What if he’s so moved by the courage of the email that he records a Lyrics of Livin’ about it? The story of what it must have felt like for me to send the email. From his perspective. Some guy from Brunswick, Maine pitching a campfire conversation and a movie idea in the same email. And at the end of the episode, almost like he’s talking directly to me, he says yes. He throws it back out into the universe, knowing there’s a decent chance I’ll see it. Because I never miss an episode.

That’s very McConaughey, if you think about it.

So now we’re at four scenarios. Two of them end well.

That’s one in two. Fifty-fifty.

Then I had another idea!

I could write a Substack post about the whole thing. Which meant there was now a fifth scenario. The post makes it to him and he reaches out.

That’s three out of five outcomes that end well. Now the odds are 60-40!

A walk on the beach just took me from 33% to 60%.

Becca had thoughts.

The Payoff

Here’s the thing though.

The point of all this was never really about getting a response.

It was about the courage it took to send the email in the first place.

I don’t view it as a negative that he might think it’s the stupidest thing he’s ever read. I view it as, despite that, I still had the courage to put my heart out into the world.

So many great ideas never leave the room they were born in. You have a great idea in your head and then you start to self-criticize. You talk yourself out of it, out of fear. Think about all the beautiful things this world would have lost if people weren’t willing to put things out there that others may not love. Think about your favorite song. Your favorite painting. Any time you put yourself out into the world, it’s a creative expression of who you are. It not landing with others can feel like a rejection of you at your core. That makes it really hard. So to have the courage to do it anyway matters.

It is also about the positive feelings I get from this thinking and dreaming.

Every time I let myself imagine how this plays out, something happens. I picture the fire in Austin. The conversation. The dinner. And my brain lights up like it’s already happening. Which means I’ve already had a campfire and dinner with Matthew McConaughey.

Research suggests that when you vividly imagine something joyful, your brain responds in ways that aren’t much different from the real thing. The emotional circuits fire. The good feelings arrive.

Your brain can’t fully distinguish between vividly imagining a feeling and actually feeling it. So even if Matthew never sees the email, I am still getting tremendous benefit from imagining that campfire in Austin.

And here’s the best part. After all my math, after all her thoughts, Becca agreed with me.

Not about the probability. She’s never going to agree about the probability.

But about the courage. About putting your heart out into the world and not waiting for permission. About the joy you get just from letting yourself believe something beautiful might happen.

That’s not delusion. That’s love doing the math.

And that now brings me to 100% probability.

That, my friends, is how the extreme optimist calculates probabilities and sees the world.