To sail is to be in constant uncertainty. The sea is never the same twice. The conditions are never the same twice. There are no two boats alike. Crews change. The experience is never the same.
That said, we’re not all racing the America’s Cup every time we set foot on the water. Therefore it’s important to set up your expectations and your level of potential jeopardy to match your particular situation. Because working sailors hard, or for too long has has an impact on what you’re trying to achieve as a leader and as a crew.
To use a software engineering example, if you’re constantly fighting system instabilities, bugs, and outages, you won’t be in a good enough place to build good, supportable code.
Leading and Teaching
To sail is to be constantly learning.
When you sail with others, whether you’re the skipper or not, you will inevitably need to learn from your boat, your environment and your fellow sailors and pass on your thoughts and ideas. You will try new things and push boundaries and sometimes you will fail.
Failure can be big or small. It can come down to an individual in a moment of panic or a carefully-arrived-at group decision.
Perhaps you’re tired, hungry or irritable. Perhaps you’re sleepy, hungover or distracted. Group decisions sometimes work, but the ship works better if a single person is in command. When a single person encourages everyone to reach a bit further and try something new.
Sometimes, we choose to lead without knowing it. Those eyes turn to you looking for direction, giving you explicit acknowledgement that they trust you.
Failure Should Always Be An Option
To sail is to try things out. We might change our heading to see if the wind is more favourable on one tack or another. Perhaps the current is better over there. There are a myriad unknowns that need to be explored. Failure is always an option.
When we build software, we are often the most effective and with the most flow when we’re working within our comfort zone. But this isn’t the zone where we will challenge the integrity of the systems we’re working in. If our goal is to “write more code” or “improve code coverage” then we should stay comfortably within it, but if our goal is to “improve our user’s experience,” we need to be more radical and take more risks.
Like in life and business, you won’t always win when sailing. Sometimes you’re going to make the wrong call and screw up. This is going to happen whether you like it or not. It’s more about how you deal with that failure, learn from it and move on as an individual.
Doing It Alone
Over the last five years, I’ve sailed in dinghies and yachts. First with instructors, then with family, and friends. All three groups of people are different experiences.
Instructors all have their favourite ways of doing things, and they are great at teaching individual techniques and blending that with your theoretical knowledge. They provide a structure for you to learn in. Family members bring their own dynamics and preferences to any scenario and perhaps make it more difficult for order to be established as other social rules have precedence. With friends, it’s sometimes again hard to focus individuals on what their tasks should be. They are there to have fun, not necessarily learn.
Training with instructors won’t teach you anything about dealing with your crew. That’s up to you. What you can do, however, is focus on the content of what you’ve learnt and use that as a common language.
As a sailor, you will always eventually be in charge of a situation. You will have to make a decision which has a fundamental impact on the safety of the boat and the crew. This doesn’t always happen at work, there are places for people to hide.
Looking around me, I see very few natural leaders emerge. Many are content to sit on the sidelines and let others make it happen. While many have opinions on code, quality, and architecture, very few want to actually be responsible for making a change.
If you are that person, you’re a leader. Whether you’re an engineer or a manager, you’re the skipper organising your crew to take a risk and possibly achieve something great.