Why Great Entrepreneurs Think Like Sailors

We were off the Australian coast in the middle of the night and in serious trouble. The headsail of my ill-equipped yacht had become dangerously entangled and we struggled for control with a storm front approaching, a big swell and the nearest port 60 km away.

I remember thinking I had made it to the 'High Life' when I had proudly purchased my own yacht. I dreamed of cruising the world’s oceans. The only catch was that I didn’t really know how to sail. (I thought I would learn on the job.) With a bit of false entrepreneurial courage, I decided to sail 250 km down a notorious stretch of coast at one of the wildest times of year. In fact, we were only one day behind the Sydney to Hobart Yacht fleet – a race considered one of the world’s toughest. 

Our ordeal lasted nearly six hours with the coast guard on stand by for a mid-sea rescue and my heart in my throat the entire time. What saved us was my friend Stuart had a wealth of sailing experience and took over command. He took in incoming data about our situation and made informed decisions accordingly, without fuss or hesitation. He engendered confidence into his crew and did not abdicate responsibility to the coast guard who would have only been able to rescue us under dangerous circumstances at the expense of the vessel.

Honing your decisionship

As dawn broke, we made it safely to port and I sort of had an epiphany. I realised that like the captain of a ship, the role of an entrepreneur is making a series of decisions and living with their outcomes. Whilst the high seas are inevitable, it is the entrepreneur’s role to grab the helm and take charge of their ship.

That’s why I encourage the entrepreneurs I work with to channel that ‘sailor’ mentality. Business success or failure can almost always be traced back to decision-making. There may be a million reasons that contributed to a certain situation but ultimately, it’s not about what happens in business it’s about what you do about it.

It’s about the decisions you make, the decisions you refuse to make or take too long to make and the simple little errors of judgment, especially during those critical moments. It’s about right decisions that went wrong over time or were not fixed fast enough and about decisions made too early without all the facts.  

Navigating rough seas

When I took a navigation course for my offshore skipper’s license, I got a good dose of how many things can conspire to throw you off course. The primary tool for navigation on a yacht is the compass. When navigating from point A to B, you need to take numerous factors into consideration to ensure you get where you want to go safely and within a certain timeframe. You need to account for the wind, tides and swell and consider your yacht's hull speed and the various obstructions that you have to navigate. And if this isn’t enough, you also have to take into account the deviation between true north (what your map says) and magnetic north (what your compass shows).

There will always be a lot of things that can throw you off your course in business. Building your skills and experience in advance (such as my friend Stuart did) enables you to better navigate the rough waters when they inevitably hit. I’m a big believer that entrepreneurs are bred, not born, which is why I focus so much energy on helping entrepreneurs develop their skills. 

Finding your passion

One of the things that has really struck me about sailors is their passion. They clearly love being out on the water. Particularly those salty, old sea dogs – the ones that practically live out there. You can’t wipe the smile off their face, whether they are faced with a beautiful clear blue day or a huge swell, gale force wind and a dirty black cloud on the horizon. There is nowhere they would rather be.

While they love what they’re doing, sailors also have a purpose. They will have decided on a destination or need to navigate a certain course. Whatever the objective, there is always a goal and they bring others along for the ride. The best sailors inspire their crew with a sense of fun and purpose. Likewise, as the captain of your business, you should aim to find your passion and always have an endgame that drives your forward. And whether you have staff or not, you need to inspire and motivate your stakeholders in the best of times and reassure them in the worst of times.

The sailor is a great embodiment of many of the traits and skills that entrepreneurs need to succeed. I’d be interested to know your thoughts – especially when it comes to navigating the ‘high seas’ of business. 

And if you’re ready to hit the water with your own business, check out some of the digital tools and programs we have at Investible to help you get started.