Summer of Sailing

During the summer of 2010 my life was point where there was some breathing room. My business was going well and did not require my undivided attention. Finances, although not in the realm of complete abundance, were stable and strong. And although I would not have chosen it to be that way, I was not in relationship – or even dating anyone.

So this triple convergence of time, money, and nobody to consider opened the door to what may be the first real ‘hobby’ of my life. I started sailing.

I had been sailing, perhaps, a dozen times in the last few years with my friend Bruce. He was a member of a Boston sailing club and frequently invited me down. This year, though, he was letting his membership lapse as he was traveling for most of the season. If I was to continue sailing, I would need to join on my own; take the classes, pass the tests, and make the hour to hour-and-a-half drive to Boston several times a week. A slight shift in my personal perspective turned “that endless drive to Boston” into “Boston is just down the road.” A monthly parking space, a few audio books, and a familiarity with the traffic patterns and shortcuts made short work of the otherwise daunting reverse-commute.

I sailed throughout the summer, moving to larger and more complicated boats as I graduated each class. With every step, a new level of oneness of with the planet; the wind, the tides, the weather unfolded before me as I hoisted halyards, trimmed sheets, called out my points of sail, and tacked and jibed around the islands of Boston Harbor. The wind in my face was breathtaking.

Near the end of August I took my final class of the summer — Night Sailing. It was in that dark that I opened my eyes.

Sailing comes at a particularly appropriate time in my life, as these things often do.

As I round the half-century mark, my life begins a shift from “Make it Happen” to “Let it Happen.” A lifelong focus on accomplishment, setting goals, striving and winning has shifted toward feeling the flow of my life and moving with it.
Row, Row, Row your boat
Gently down the stream
Merrily, Merrily, Merrily, Merrily

I turned my face into the wind, letting the whistling breeze over my ears speak to me.

The Wind said, “I am a sea-breeze today. I’m coming from the East, from the cool sea to the warm land. The heat of the city causes the warming air to rise to puffy white Cumulus clouds above. I am rushing in across the ocean to take its place.”

I pulled the rudder slightly toward me, heading upwind to leave the harbor. The mainsail luffed a bit as I did, so I tightened the main sheet. I could feel the pull on the boat as the now neatly trimmed sail caught the wind just right. The jib could have been trimmed as well, but I let it be. My sails were set in a “Close Haul” tack and I was heading nearly upwind.

“Going with the flow” does not suggest the passivity of being blown around to wherever the flow happens to be travelling. I still choose my destinations but I move in partnership with the forces around me. It’s dancing with the wind rather than fighting it.

In business, this suggests that I look at what my customers want and have a clear picture of the skills and desires of my employees. If I take my own ego out of the picture then I am no longer trying to sell customers what I want them to buy and extorting employees to do what I want them to do. Rather I have a team that wants nothing more than to spend their day giving customers just what they’ve come to my website to buy.

In relationship, I have no idea what this means. Finding out is, perhaps, my next journey.

As the sun sets, the wind dies completely. This is how a sea-breeze always behaves. When the city cools, the air stops rising, the sea turns to glass, and the air goes still and silent. Out here on the water there is not a sound – no birds, no crickets, no deep thrum of distant engines throbbing at the edge of perception through the ground.

When the stars come out in the total silence, it is a symphony. And they move in the night, as if blown by the wind that has, until morning, abandoned me.

Now it’s time to start the motor and come home. When I’m a more skillful sailor I’ll sleep out here. Perhaps it will be silent and still like tonight. More likely, though, there’ll be a slight wind and a swell to the sea and I’ll rock slowly, listening to the creak of the boat, the tapping of the halyard on the mast, and the lapping of the waves on the hull.
…Life is but a dream.