6 Things Sailing Has Taught Me About Running A Business

I have raced sailboats for the past fifteen years, and been a business owner for ten. In that time I have come to recognize some parallel themes that apply as much to skippering a boat as they do to running a small agency. These insights aren’t mission-critical, but when taken as a whole they act as sage advice to help anyone who manages people.


If you’re on a racing sailboat, it isn’t by chance. You either own the boat, you’re on the crew, or someone invited you to come along for the ride.

Whatever the reason, once racing starts, there is work to be done!

Some jobs on a boat require consistent vigilance – the helmsman needs to drive fast and in the right direction; the trimmers constantly set the sails for maximum power; the tactician surveys the course to make moment-to-moment decisions.

Other crew might appear to have less urgent jobs. You’ve seen pictures of people hanging their feet over the water and looking at the boat next to them. But they have active and important roles too – their weight and position on the “rail” help level the boat to go faster; they communicate changes on the course to the guys in the back; and during maneuvers they handle critical changes in sails, lines and equipment.

The crew we have on board on race day usually has the experience and abilities to help us get around the course quickly – and everyone has responsibilities.

In business it’s the same. In a small office, every job is critical. The people we work with are the ones we’ve chosen to “race” with. They each have responsibilities that, when executed properly, give us more chances to win.

In a world where good employees often “jump ship” for other opportunities, it’s important to affirm their value, and provide them the tools they need to take responsibility for their part of the business so they can make a contribution.


Once the boat leaves the dock, the crew is confined to a vessel that is sometimes cramped, and usually very busy.

Although teammates have come and gone through the years, our boat has a core group who have sailed thousands of miles together and are very familiar with one another. This situation can be both a positive and a negative.

On one hand, we share an easy understanding of how to push the boat and each another through a race. This is a plus for obvious reasons.

On the other hand, however, it can sometimes be difficult for a new person to fit in or find opportunity among such seasoned hands.

In a small business we must be conscious of how a new hire (or the loss of an employee) affects the group. It’s not okay to hire the boss’s wife or someone’s best friend without first considering how that change will manifest itself across the operation. If existing employees feel confused or threatened by new chemistry, you risk losing them – and you’re left with the boss’s wife instead.

And when bringing the new person in, it’s important to take the time to acclimate them to the office environment and make sure they feel welcome as an important part of the team. (See point #1 above!)

Sometimes on the boat we try out someone new and it just isn’t a good fit, for whatever reason. When bad chemistry happens, it’s important to remove the problem quickly. Disagreement or discord isn’t going to help win new business or sailboat races, and is likely to alienate important team members.


Especially on a sailboat, this seems so obvious – isn’t the objective to win the race?

Of course this is true – but races are won or lost based on the nuanced decisions that are made prior to the start. Considerations include where you want to be on the line, what side of the course to take, and what sails to use.

My favorite races are the ones where we discuss the strategy (what we want to happen), and then execute through tactics (how we manage the course during the race). When you go in with a plan, you’re ready for anything – including winning!

All too often I see crews start races without these conversations. Their egos get in the way, and they often wind up following the leaders instead of being the leader.

I see this all the time at work. There is an assumption that everyone knows how we’re going to make money. That’s rarely the case. Stakeholders need to routinely make strategic decisions to manage the business for success, and those plans need to be communicated to every employee through established methods so the team is cohesive and working in the same direction. It’s just good practice.


It’s impossible to win a race by accident. Sometimes you need some luck to come in first, but you still have to be prepared – because there are simply too many other good sailors out there who are trying to take your victory from you! The more you practice, the better prepared you’ll be to take advantage of opportunity on the course.

It’s hard to “practice” business, but you can do two things that are instrumental to success:

  1. First, instill a culture of “best practices” so you are working to industry standards. In our business this means exercising protocols for communications, file sharing, collaboration and other processes. If something isn’t working or is falling behind the times, it’s my job to assess the deficiency to make sure we can do our work and remain competitive.
  2. Foster a culture of creativity – especially if you’re in the creative business, which we are. I’m so proud that the people I work with have outside interests that inform the work they do here. From metal working to ballet to painting to sailing, the skills my staff hones elsewhere pay off in ideas and execution at the office. Their interests make them more interesting workmates, and create a well-informed workplace. So I look for chances to engage with employees about their interests, and opportunities to leverage their experience in the work that we do. This is their “practice,” and our business benefits as a result.


When I bought my first boat the guy who sold it to me said, “Don’t be afraid to look like an idiot at least once every time you get on the boat. That’s how you learn.”

To this day I do things that make me look like an idiot – both on the boat, and in the office. (I hope I’m still also putting myself in a position to learn from those mistakes.)

In both worlds the judgment of the skipper is frequently brought into question – often by himself. In my experience, it’s better to make a decision – even a bad one – than no decision at all.

Sometimes on the racecourse a skipper might decide to take a flyer and separate from the fleet. On the rare occasion when it works, you’ll reach the next mark ahead of the other boats. More often, however, you break away only to fall farther behind. As the guy in charge, win or lose, you’ll have to live with that decision until the next race.

At work I’m not in a position to take a lot of flyers. But I can still make mistakes, just like everyone else.

When that happens, it’s helpful to remember that very few mistakes are fatal to the business, and the competition is going to make some poor choices, too.

In sailing, business, or the rest of life, it’s critical to learn from those mistakes, and to try to minimize the damage. We all live in glass houses, and the sooner we accept our flaws, the sooner we can do something about them.


All of us have chosen to spend a portion of our lives with one another. On the boat, my fellow weekend warriors and I steal time away from shore so we can enjoy the sport of Kennedys and kings. At the office, I’m lucky enough to be surrounded by interesting twenty- and thirty-somethings that have the world at their fingertips, and have waylaid with me for a while.

In both scenarios, being together matters. Victories are sweeter and defeats are less bitter when faced as a team.

Sometimes – especially in the defeats – that togetherness is hard to come by. There are moments in every race that define the outcome, and in defeat, it’s not uncommon for crews to start pointing fingers.

In the end, what a waste of energy. Blaming one another won’t change the result; it simply casts a shadow over the entire experience. And remember – this is sailboat racing – it’s a privilege to even be out on the water! Unless you’re a professional, a race isn’t a life-altering event, and the grandeur of the day shouldn’t get mired in the blame game.

One of the hardest things I have had to learn in life and in business is how to stow my own frustrations and turn them into constructive outcomes. When something goes wrong in a small office, it’s easy to complain and make everyone uncomfortable. It’s helpful to remember that we’re going to win some, and we’re going to lose just as many. The mistakes we make along the way are opportunities to learn from and evolve. So we need to minimize them and move on – together.

Whether you’re at the helm of a boat or a business, there is no substitute for experience. But you have to start somewhere, and it’s nice to know there are circumstances throughout life that can inform the way we make decisions. If you’re in need of a great creative marketing firm, I hope we can work together some time. If not, that’s okay – come sailing instead.

@visaviscreative | www.visaviscreative.com

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