On Wind, Water, and Intent

For me, magic happens where wind meets water.

Anyone who’s sat at the tiller of a sailboat knows the sound: the rush of water against the hull and the steady hum of breeze in the canvas. It is all at once meditative, deeply calming, and wildly exhilarating, but always entirely honest.

My path to the wind and the water wasn’t planned. Decades ago, while coaching track and cross country at a private prep school here in Birmingham, two brothers from a local sailing family asked if I would sponsor a new school sailing club. Having never set foot on a sailboat, I hesitated. I told them I couldn’t sponsor a club for a sport I didn’t know; I had to learn first.

That decision opened the door to a whole new world. Every Saturday morning for over two years, from Labor Day to Memorial Day, I showed up at the docks of the local club. They raced under PHRF—a handicap system that allowed entirely different types of boats to compete on the same course, using calculated times to determine the winner. Week after week, I volunteered as crew for whichever captain was short-handed. Because PHRF racing brought together everything from heavy-displacement cruisers to nimble racing sloops, I learned the art of sailing on a wide variety of vessels. Adapting to different rigs, sail plans, and tiller responses taught me seamanship at its core—how to handle a boat regardless of the hull under my feet, absorbing tactics, wind-reading, and strategy from the best skippers on the lake.

Eventually, an opportunity came to buy one of the fastest boats in the club. I took the helm as skipper, using the collective wisdom of every captain I’d crewed for to eventually beat them all on the water. I named her Aeolian. After a few years of lake racing, my friend Jim, my crew and I would step the mast, trailer Aeolian down to the coast, and put our skills to the test in full-day bay and ocean-based races. I was hooked.

When taking friends out on open water, I loved handing them the tiller and laying out a simple choice, governed entirely by their intent:

“We can go with Option A: pick a specific destination, plot our course, and execute a series of calculated tacks and jibes. That means constantly trimming the sails to every shift in the breeze, factoring in currents and the tide, then taking rigid control, and forcing the vessel to serve our purpose of reaching our pre-determined port.

Or, we can choose Option B: set the sails and trim the sheets—and then surrender to the elements. You let go of the need to dictate where you land, using the tiller simply to yield to the wind and the water, guiding the boat wherever the two together fill your canvas.”

For me, there is a raw, exhilarating freedom in keeping her powered up while allowing the currents and breeze to set the course—to feel the boat heel leeward and listen to the water rush along the rail. When you surrender to the elements, there is no 'wrong direction’ and no clock to beat.

They say the two happiest days in a sailor’s life are the day he buys his boat and the day he sells it. At 63, my boat is long since sold, but the lessons of the tiller remain.

Looking back, I realize that for decades, my career was an exercise in that Option A racing mindset—defining fixed coordinates, optimizing performance, trimming the sails for maximum speed, and navigating the handicaps to cross the finish line ahead of the fleet. It took sharp focus, and it served its purpose for that season.

But living with joy in my later years requires a fundamental shift in how I navigate. It isn’t about stepping off the boat, dropping the sails, or backing them and aimlessly drifting; it’s about continuing the sail, but making a conscious choice to trade the stress of holding a rigid course, for the quiet, calm wisdom and exhilaration of the simple act itself.

Option B still takes active effort—doing what I can do each day, staying engaged, managing the heel of the boat, and keeping the canvas full—but it allows me to truly surrender to the greater wisdom of the elements of life.

Listening again recently, it struck me that Christopher Cross captured much of this beautifully in his classic anthem, Sailing:

“Well, it’s not far down to paradise

At least it’s not for me

And if the wind is right you can sail away

And find tranquility

Oh, the canvas can do miracles

Just you wait and see, believe me...

Sailing

Takes me away to where I’ve always heard it could be

Just a dream and the wind to carry me

Soon I will be free”

To sail without a final destination isn’t about being lost; it’s about the serenity found in trusting yourself, letting go and believing that in the end, as my mother would say, “everything always works out for the best.”