Born a Pirate 100 Years Too Late (or So I Thought)

There are childhood phases, and then there are childhood truths; those ideas that stick long after the plastic swords break, the costumes fade, and everyone else moves on to something more socially acceptable.

Mine wasn’t cops and robbers. Not cowboys and Indians. Not even the predictable neighborhood sports mythology. It was pirates.

Not the sanitized, theme-park, gift-shop version. Not even the Johnny Depp, eyeliner-heavy swagger that came later with Pirates of the Caribbean: The Curse of the Black Pearl.

Mine was something older and less curated. A rougher imagination. Salt-stained. Wind-driven. A life that didn’t sit still long enough to ask permission. Somewhere along the way, I picked up a phrase that fit too comfortably to ever really shake: I was born a pirate 100 years too late.

At the time, I meant it literally enough to believe it, but vaguely enough to never explain it. Now I think it meant something else entirely.  While other kids were negotiating rules of structured play—who’s “it,” who’s “out,” who’s playing fair, I was more interested in systems without referees.

The ocean made sense to me in a way playgrounds never did. Not because it was calm. It wasn’t. But because it was honest. Wind doesn’t negotiate. Waves don’t vote. The weather doesn’t care about your schedule. Somehow, that felt more trustworthy than anything built on chalk lines and boundaries. So yes, I preferred pirates. But really, I preferred movement without permission.

We should be honest about what we were actually imagining. The pirate life, as it lives in memory and myth, looks like this:

• Open water and endless horizon
• A chosen crew instead of assigned roles
• Loyalty forged in storms, not meetings
• Freedom that looks suspiciously like rebellion
• A ship named something dramatic, preferably weather-related

It’s easy to romanticize because it removes friction between desire and action. Want to leave? You leave. Want to change direction? You turn the wheel. Want a different life? You take it. No forms. No approvals. No waiting for consensus. Just wind, wood, and will.

The actual pirate life—especially 200–300 years ago—was something else entirely. Less poetry. More pressure. Shorter lives. Brutal conditions. Disease in cramped quarters. Violence that wasn’t stylized or choreographed. Hunger that didn’t resolve in a montage.

Even that version contains the part that still pulls at the imagination. Beneath the danger was something rare: immediacy. Every decision mattered faster. Every risk had weight. Every storm was real, not metaphorical. There was no pretending you weren’t accountable to the sea.

So why did that world—real or imagined—feel like home before I ever knew what it cost? It probably wasn’t the water alone. It was what the water represented.

• A comfort with uncertainty that others tried to eliminate
• A willingness to make decisions without full visibility
• A preference for motion over maintenance
• A habit of choosing direction over certainty

In hindsight, it wasn’t piracy I was drawn to. It was navigation under pressure. Some people are built for optimization. Others are built for mid-storm course correction. I’ve always been closer to the second group. Which explains a lot more than I used to admit. You only need to reread the Still Standing series to fact-check me.

There are moments when imagination stops being visual and becomes auditory. For me, it shows up in songs like Jimmy Buffett’s “Son of a Son of a Sailor.” I was never a full-fledged Parrothead, never committed to the beach-chair philosophy of it all—but something in that song still lands differently. It doesn’t feel like music. It feels like a memory that doesn’t belong to a specific lifetime.

Then there’s Kenny Chesney’s “Pirate Flag,” that modern, sun-bleached version of escape and horizon-chasing. It’s easy to dismiss it as romanticized island mythology—but still, something in it pulls at the same thread. Not because I wanted that exact life. Because it sounds like a life where the sea is still part of your identity, not just your scenery.

Life doesn’t really offer wooden ships anymore. It does offer substitutes. Mine happens to be a Kia Niro, nicknamed, ironically, the Black Pearl. Not a vessel of conquest. Not a symbol of rebellion. Just motion.

Errands instead of expeditions. Roads instead of oceans. But still: movement through unpredictable conditions, still steering through weather that doesn’t always consult your plans. The scale changed. The impulse didn’t.

At some point, the childhood imagination stopped being a game and started becoming a job description. I had the privilege of serving as an Assistant Sailing Director at YMCA Camp in the Ozarks and later as Sailing Director at Camp Champions. Something interesting happened there. The fantasy didn’t disappear. It matured.

The wind was still the wind. The water still demanded attention. The boats didn’t care about ego or story—only skill and awareness. What changed wasn’t the environment. It was the responsibility inside it. Somewhere in those summers on the water, I realized something simple but lasting: this wasn’t just a childhood phase. It was a direction I had been rehearsing for years without knowing it.

There’s a misunderstanding that needs clearing up. Pirates, in the fantasy sense, look like escape artists, people running from something. The version that actually resonates with me has always felt different. Not escape, but engagement without guarantees. Not avoidance of responsibility, but acceptance that responsibility sometimes arrives without warning, and still must be met.

That distinction matters. Because one is fantasy. The other is just adulthood with better metaphors. If I strip away the ships, the flags, the cinematic storms, and the mythology, I don’t think I ever wanted to be a pirate.

I think I wanted to live in a way where:

• The horizon still mattered
• Decisions still had weight
• Courage still meant something slightly uncomfortable
• And life still required reading the wind instead of following a script

In other words, I don't want the chaos. Just poetry in motion, the freedom of the open seas. It was, and still is, a love affair with the water, not as escape, but as return.

As I navigate this post back to shore, here is my final course correction. We don’t usually get the lives we imagined as children. Sometimes we get translations of them. Smaller vessels. Narrower seas. Quieter storms. Occasionally, if we’re paying attention, we realize the pirate life wasn’t ever about piracy at all. It was about refusing to live entirely dry-docked.

So maybe I wasn’t born a pirate 100 years too late. Maybe I just learned, over time, that the ocean was never the point. The point was always the decision to leave shore, from time to time, and keep on moving towards that golden horizon.