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How Captaining Sailboats Prepared Me To Navigate Business Turnarounds

You don’t run a business by compass, but there are several ways a ship and a corporation are all too similar.

 Manuel Breva Colmeiro/ Getty Images
Manuel Breva Colmeiro/ Getty Images

In my early twenties, I followed my youthful dream of becoming a sailboat captain, eventually becoming certified and competing in the World Sailing Championship as a bowman. It was a thrilling and rewarding experience, and I‘ll always treasure my years spent on the sea. While I still love the water, I eventually switched career paths to something a bit more terrestrial but no less compelling for me: the world of private equity and business turnarounds.

As I grew my career helping businesses find their bearings, I noticed a great number of similarities to my previous line of work. Being a leader, whether the captain of a boat or a CEO in the boardroom, takes a number of skills and strategies. These are a few of the ways I’ve realized leading a ship prepared me to lead a portfolio company.

Know the basics

When I first began sailing as a young man, I knew I’d never excel at it without mastering all the little things. For this reason, I took up with a sailing school in France which taught the old-school way: no GPS, no fancy equipment. We calculated distances using the stars, triangulation, and analog instruments. There was a bit of romance to it, sure, but more important was the fact that I’d be ready whenever electronic guidance systems failed me.

You don’t run a business by compass readings, but the need to understand the fundamentals is all too similar. Every company wants continual growth, that’s no secret. But without knowing how your business functions at the most elemental level, scaling up can be a disaster, like steering a ship with no idea of where you’re going. Understanding why decisions need to be made takes a detailed understanding of how your business works. No amount of high-tech hardware can replace that knowledge.

Many must become one

Plenty of sporting activities require teamwork, but few have the high stakes of competitive sailing. On a swiftly moving sea vessel, every team member needs to act in perfect concert to execute on tasks. Without unified effort, your boat’s carefully planned route becomes a distant memory in an instant, in races where every inch matters. An effective crew can act as one, each moving part of the boat (and there are many) handled by a capable, cooperative group.

As leader, assembling and supporting this team is the most important task you have. As much as you guide the direction of your entire organization, it’s up to them to bring your vision into reality. Coalescing a team takes time and effort, but it pays off in droves when everyone is on the same page, bringing ideas to life and executing on key initiatives. Much like navigating rough waters, developing a profitable business won’t happen without the efforts of many people working as one.

Always take the temperature

There’s also the need to know what’s happening outside your crew as well. A good captain reads weather reports closely in order to prepare for what’s coming next on the waters. Even so, those forecasts are just predictions, and cannot be trusted 100% to tell you what you’re about to sail into. Your next moves must be based on knowledge, experience, and a keen sense of what your boat can and can’t handle.

In the boardroom, you have market forecasts. Just like weather predictions, there’s an element of needing your own judgement in order to get the most use out of them. You must batten down the hatches when tough times are expected, and put your sails in position to ride upswings and robust markets all the same, all the while relying on your own intuition when the forecast doesn’t match up to reality. A business leader can never let their view get cloudy; the outside world must always be seen in clarity, lest your competition’s sight go further than your own.

Be ready for anything

Being a boat captain brings a huge measure of responsibility in multiple ways. You can marry people, give last rites, and most importantly provide a steady, certain hand when things aren’t going well. That means making tough decisions and following through on them. A sinking ship is like a sinking company–you need to decide what goes on the lifeboat and what needs to be jettisoned, and fast.

Every day brings something new, on a boat and in a business, and great leadership shines brightest when handling the unexpected. You might have a torn sail or an instrument failure, but you still need to bring your vessel back to dock. Being ready to meet new challenges was a perpetual state of being in my seafaring days, and leading companies in complex turnarounds requires the same dexterity. The life-threatening aspect may not be there, but the idea of letting a business under my purview lose it’s way feels just as perilous. Staying versatile and ready for the next obstacle keeps that fear at bay. It’s a matter of attitude.

There’s good reason that we find so much inspiration from the sea. The risk of navigating a wide and unforgiving ocean relates to building a professional career in so many ways no matter which line of work you enter. Turning around businesses gives me the same rush I once got from taking a boat to sea, and while I often miss the sailing life, the teamwork, leadership tasks, and need for awareness that I’ve found in business often has me feeling like I’m still on the boat, steering wheel in hand. It was quite different from business school, but gave me incredible lessons all the same.

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