5 Design Lessons from Sailing The Chesapeake Bay

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Since the beginning of April 2021, me, the hubby, and our sailboat, Flingo Bingo, have been putting around the Chesapeake Bay. Our only game plan was to sail as much as the weather permitted, and explore as much of the bay as we could. Having already lived aboard our boat for eight months at that point, we were ready to get off the dock and into an adventure.

As with all journeys, we tend to learn a bit more than we expect. Here are some of the lessons I learned about design, right here on the water.

Anchored out in the Little Choptank River.

Test often and early.

One of the greatest mistakes any designer (web or UI/UX) can make is to keep working on a project until it is perfect. The only way to really know if what you are building actually works in the real world is to launch now, fix it later. The same can be said of sailing – we could have spent two or three years improving our rig, setting up more complex systems, and more. But instead, we started the journey, figured out what we really needed to keep us going, and improved. Design, and sailing, is a work in progress – you’ll never perfect it, so just get out there, learn, and improve your work.

Set the sails and enjoy the ride. Point Lookout to Solomons Island.

Go for it.

I am the type of person to jump into the deep end when it comes to new experiences. For example, when I started out as a designer, I was using Canva and just learning Adobe products. Even so, I managed to get contracts with NGOs designing posters, reports, infographics, and more. Most of the time, the best way to get into design, or level up your skills, is to take a leap of faith. I can say the same for sailing – when you are out there on the water, at the mercy of Mother Nature, anything can happen. But if we never left the dock, we wouldn’t have become better sailors.

Weather eye on the horizon. Solomons Island to Oxford.

Do your research.

Non-designers might not know this, but good design takes a lot of research. Understanding who the design is for, what has worked and doesn’t work, and the message being portrayed are all part of the research portion of designing anything. When we are planning a sail, we have to do quite a bit of our own research – reviewing charts for water depths, looking at wind direction and speed, and local knowledge all play a factor when deciding to leave port. Being well-informed, and asking lots of questions, will make design projects and sailing more fun and productive.

From Coles Point to Point Lookout in the Potomac.

The road is 360°.

Design problems need to be approached with an open and creative mind. Many designers will fall into the trap of looking at problems from one angle, due to bias from a client, or simply being exhausted. Luckily, design encourages us to think outside the box. Design isn’t a road from point A to point B – like out on the water, our road is all around us. When going in one direction means beating into the wind and making no progress, change your tack and find a new heading.

Sunset at Colonial Beach, VA.

Listen to the world around you.

Designers need to keep an ear to the ground at all times. Whether we are listening for design trends, culture shifts, or simply reading between the lines for a client, being observant is incredibly important. Asking questions and listening to answers given will make the difference between creating a design that works, and one that falls short. When it comes to sailing, we are always listening to the elements – the sound of the wind and waves, noting our direction, and listening for other traffic on the water. Our observations guide us in design and on the water.

After five months of cruising around the Bay on our dear Flingo Bingo, I know there is still so much more to learn. Sailing has encouraged me to become more bold with my design projects, and to observe trends in culture and design. Here’s to embracing the adventure, and all it has to teach us.