Lessons from sailing

I’m taking sailing lessons.

I’m learning how to sail.

On my “maiden voyage” - my first time alone on a tiny Mercury sailboat on the Charles River, I glided out from the dock and immediately caught a gentle breeze. I was off! I spent almost an hour just feeling into the wind. Intuitively adjusting my sail to allow more or less air to fill it. When it was time to turn - to tack - I felt my way into it. Turning the rudder until my sail shifted to the wind from the opposite direction. Colored yarn tied to the sidestays - and the wind on my face and in my ears - was the indication of the wind’s direction. 

There was a father with his young son skillfully navigating the open water. I paused to watch him tack - swiftly and elegantly - then catch the wind again. I could clearly see what he did. Tiller push all the way away from his body, the boat turns into the wind, then keeps turning away from the center, straighten out the rudder, and catch the wind again.

I tried it. I did it! I practiced that move. Feeling when it was right. I felt so free.

The father and son caught another gust, their boat tipped sharply to the side. The father leaned out to balance them and they hooted with glee. “Wheeee! Whoohoo!” The son, cheering for them.

The instructor spotted me out in the open water, motored over to my small skiff, and said “we’re all over there on the course.” I’d been scolded. 2nd grade again. “Oh, I’ve just been practicing out here. And I’ve been doing great!” “Nothing wrong with practicing” she said. “I wonder if you could try gybing (or jiving as she wrote on the whiteboard in the classroom.) That’s the more scary one.”

“Yeah. I can try.” I readied myself and turned the boat into the wind, shifted sides of my seat, and caught the wind on the other side.”

“That was very nice.” She yelled. “That’s what we call tacking.”

I laughed. Genuinely amused by my earnestness and the error.

After clarifying what the elements of gybing were, I prepared myself for doing something risky. Something scary. And then I made the moves I’d been told to make. Pull the tiller toward me. Let the sail come in. Everything sped up. I fell to the bottom of the boat, the sail swung over me, the rudder jammed sharply, the boat tipped threateningly close to capsize, I let the sail out to release the pressure of wind, recovered my seat, straightened the rudder. My heart pounding, bruises welling on my thigh and wrist.

“OK, that was pretty good. You have a good handle on sail control, just remember to balance your weight in the boat by moving to the opposite side earlier. Would you be willing to come to the course and practice some more? It’s just going to take practice to get it.” 

Yes, I’d be willing.

I realize that for a lot of us - entrepreneurs, we out on the frontier who are creating something completely new may be following an intuitive sense of what we’re doing. Feeling when the wind catches the sail. When turning into something gives us speed, and when it causes a spinout. It’s lonely and often painful. The bruises are a lasting  reminder of our hard lessons.

And then there’s the defined course. A clear set of goals to be achieved with the structure of a system. Something that millions of sailors before us have learned and practiced: Tacking, gybing, keeping the mainsheet at 90 degrees, using the telltales to signal the wind direction, holding the tiller and mainsheet line so they’re not lost, moving at the proper timing.

I tend to voyage alone into open water and rely on my intuition.

The foundational knowledge is there - available to me when I’m willing - those “rules” I've spent most of my life rejecting: “Rules are for sheep. Those who don’t have the courage to set out uncharted.”

And I’m now seeing that it’s an advantage to have both. The foundational structure that keeps me safe, that makes me a more skillful sailor. And the courage to trust my senses. To lean into my intuition as a guide on the open water.

My body is still swaying from yesterday’s outing. I’m listing in my desk chair, eyes closed, gyroscoping to my center.

A wise beginner sailor. 

Ready for the next trip out into the wind.