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First Sail

Charlie’s first time on a sailboat. Monterey Bay at sunset. Three years old and already braver than his old man.

Here’s something to know when you take your kid out on the water for the first time: you’re terrified. Not of the ocean, I know the ocean, respect it, understand that it doesn’t give a shit about my feelings or my careful planning. I’m terrified of being the father who fucks this up. Who makes him scared of something beautiful. Who ruins the moment by being too cautious or too reckless or too whatever inadequacy I’m carrying around that day.

But there he is. Sunset light turning everything gold and impossible. The wind’s steady, the boat’s heeling just enough to feel alive, and Charlie’s looking out at the water like he’s seeing the world for the first time. Which, in a way, he is. This is his first time understanding that the horizon is not just a line but a promise. That movement can be silent. That wind has power. 

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Sail Forth- Steer for the deep waters only. Reckless O soul, exploring. I with thee and thou with me. For we are bound where mariner has not yet dared go. And we will risk the ship, ourselves, and all.
Walt Whitman

Walt Whitman got it: “Sail forth—steer for the deep waters only.” Easy to say when you’re writing poetry, harder when you’ve got a three-year-old who can’t swim yet and his whole life ahead of him and you’re responsible for not being the asshole who traumatizes him before he’s old enough to have real memories.

But here’s the thing: he’s not scared. I’m scared. He’s just… present. Taking it in. The way kids do before we teach them to be afraid of everything, to calculate risk, to worry about all the things that could go wrong instead of just experiencing the thing that’s happening right now.

Monterey Bay at sunset is one of those places that makes you believe in something bigger than yourself, even if you don’t know what that something is. The kelp forests below, the whales that sometimes surface, the cold Pacific water that’s been traveling for thousands of miles just to arrive here, now, at this exact moment when my son is seeing it for the first time.

I’m thinking about all the times I almost didn’t do this. All the reasons not to: too young, too risky, too much could go wrong. All the ways fear masquerades as prudence. All the moments I could have stolen from him by being too careful, too worried, too convinced that my job is to protect him from everything instead of showing him how to navigate it.

The boat heels. Charlie laughs. That’s it. That’s the whole story. A three-year-old laughing because the boat’s tipping and the wind’s blowing and the water’s rushing past and none of the rules that govern his small contained life on land apply out here.

“Reckless O soul, exploring.” Yeah. Reckless. Taking a toddler sailing. Believing that he needs this, needs to feel small against something vast, needs to understand that the world is bigger and stranger and more beautiful than the confines of his bedroom or his backyard. Reckless to think that a father who’s made every mistake possible might somehow get this one thing right.

But the light’s fading now, turning everything purple and pink, and Charlie’s still watching the water, still taking it in, and I’m thinking: this is what I’m supposed to give him. Not safety, safety’s a lie we tell ourselves. But this. Experience. The understanding that the world is worth exploring even when, especially when, you don’t know what you’re doing.

We’ll risk the ship, ourselves, and all.

Damn right we will.

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