Captaincy | Seth’s Blog

I’m not sure this is the right word for it, but we certainly need one.

Not ‘entrepreneurship’ which is a distinct skill. That term is usually reserved for people who start at zero and get to one, and mostly for people who operate in small businesses creating financial value through assets and equity.

But what about the person who navigates an important non-profit through changing times?

Or a product manager you can trust to not only ship the next solution on time, but to do it with unexpected improvements and a team that ends up better as a result of the journey. Some salespeople have it, guiding a complex transaction, and others don’t.

Captaincy describes someone who doesn’t just go to meetings–they change the outcome of the meeting. Someone who doesn’t depend on authority but is eager to take responsibility. It’s not about having a great idea… it’s about leading when the great idea collides with reality.

Winston Churchill and Ellen Johnson Sirleaf showed up as captains when that skill was really needed. So did Alexander Hamilton, for a while.

Captains set the agenda, create tension and lean into possibility. Captains aren’t just doing their job, they’re creating something that others thought was unlikely. They rarely have all the answers, but they’re very good at asking questions.

The difference between a successful artist and a painter is that the artist becomes captain of the creative arc, determining where and when to show up and what impact they seek to make.

You might not always want to choose a captain to join the team. A founder-led organization thinking about succession plans might prefer to hire a capable, persistent bureaucrat, someone who can reliably follow the model that’s already in place. A restless search for a new problem to solve might not be as valuable as simply doing a really good job on the existing problems.

Alas, we don’t teach ‘captaining’ in school. Sometimes, it arises, almost accidentally, in school sports and clubs. In fact, the culture of high school usually fights to make it go away. We don’t make it easy to describe on a resume, and there are no good tests for it.

It’s a skill, certainly, and ultimately a choice. We can model it, support it and create an organizational culture that makes it more likely to occur.

First, let’s name it and go looking for more of it.

November 14, 2025