The Organizing of Humans

I spent several years working in marketing. In the early days, one of the things my agency focused on was how people naturally organize themselves into groups.

At the time, we called them “clusters.” Other agencies called them segments. Eventually, the word “community” became the preferred label.

The idea was straightforward. Use data — mostly demographics — to identify groups of people with shared characteristics. It made marketing more efficient and, ideally, more personal.

And honestly, it worked pretty well.

Since I started cruising, I’ve spent a fair amount of time thinking about how the sailing community organizes itself. At first glance, the patterns seem obvious.

There’s the older retired group. People later in life who sold the house, bought the boat, and now spend most of the year moving from anchorage to anchorage.

There are families with children. Homeschooling their kids while island hopping through the Caribbean.

There’s the younger crowd who skipped the van-life trend and bought an old monohull instead, attracted by the romance and freedom of sailing.

There are the early retirees. Younger than expected. Finished with corporate life and now exploring the world on their own timeline.

And then there’s the charter crowd—people who enter the sailing world a few weeks at a time.

If you were building a data model, this is probably how you would segment the cruising community.

And yet… it doesn’t always organize that way.

I own a Balance catamaran. The moment another Balance shows up in an anchorage, the boats connect. Almost immediately.

Same builder. Similar philosophy. Similar priorities.

Without saying it directly, the boat itself signals something about what you value. Performance matters. Offshore capability matters. Design matters. The community forms naturally around that shared decision.

That one I probably could have predicted.

One I did not expect.

Sailing is incredibly global. Boats from everywhere. Europeans, Americans, South Africans, Australians, French, Swiss, etc. You constantly meet people from different countries, backgrounds, and lifestyles.

And when you sail internationally, you fly two flags: the courtesy flag of the country you’re visiting, and your home flag.

Which means you always know where people are from.

What surprised me this season was realizing just how large the Canadian cruising community actually is.

If you use the G7 as a rough proxy, Canada represents only about 5% of the population—roughly 40 million people out of about 800 million.

But in the Caribbean cruising world, Canadians feel vastly overrepresented. Some anchorages have 20–25% of boats from Canada.

It’s almost impossible to arrive somewhere and not find another Canadian boat nearby.

And that led to one of the more interesting moments of the season.

The Olympic men’s hockey final.

Even though Canada lost, the turnout at this tiny Caribbean bar was overwhelming. In a remote part of the world, hundreds or thousands of miles from home, Canadian cruisers showed up in force. We self-organized.

And what struck me wasn’t really the hockey.

It was the immediate sense of familiarity.

Shared references. Shared humor. Shared assumptions about the world. A quiet sense of community that, when you actually live inside Canada, is easy to overlook or take for granted.

Maybe that’s the interesting thing about human organization.

You can build as many models as you want. You can segment people endlessly with data and analytics.

But sometimes the strongest communities are the most obvious ones. The ones you take for granted.