The picture was taken at a museum just outside Portsmouth, Maine. It’s a photograph of the harbour in the late 1800’s.

I love sailing, even if I have not been in years. My dad bought our first sailboat when I was about six, a small wooden boat called a Penguin. Maybe 12-15 feet long. He was a self taught sailor. He bought the boat first, then read some books and we went down to the James River, put it in, and learned how book learning translated into actual sailing.

The answer is, not so much. Sailing is a mix of knowledge and reflexes, learning what each shift in the wind, each change in the current does to your boat and it’s trajectory. That constant change is something books don’t teach you.

The first time we went sailing, I was terrified. It was a choppy day in September. I sat near the front of the boat, and this thing that would lean over each time a gust of wind hit the sails, would plow through the waves and wakes of the ships on the river shook me up. In my six year old world, things, even boats, were supposed to stay level, predictable, steady and this was none of the above.

Then we plowed into the huge wake of one of the cargo ships that travel from the Ocean to the ports south of Richmond. A huge wave poured over the front, slamming into my dad and I, leaving water in the bottom of the boat. According to my dad, I tried to climb the mast, I was so afraid.

It is a wonder I ever got in a sailboat again.

But I did. I don’t remember if my dad bribed me, threatened me or shamed me. Or maybe I just got my dander up and was determined not to be defeated. I do that sometimes. But I did get back in the boat. And came to love it.

I was about twelve when my dad dropped sailboats and had a few year fling with speedboats. They were all my six year old self could have wanted. Steady and straight, they drove through waves with sheer power. You always felt safe and secure in them. But by then, I was ruined. I missed sailing, the unpredictability of it, the need to constantly monitor and adapt to wind and wave and currents. In light winds, it was the most peaceful thing ever. In stronger winds, there was a presentness that you had to have that was exhilarating.

I missed it so much that I bought my own sail boat at 14, and sailed it into my thirties.

After his fling with motorboats, when I was in my early thirties, my dad turned back to sail. This time it was a larger wooden boat. It was about forty years old and needed a complete restoration. He had it dropped in his back yard, bought some books on boatbuilding, and went to it. Yes, that’s how he did most things. It took three years to restore and we sailed it on the Chesapeake bay for years and years until he became too old, and too interested in other things, to keep it. By then, I had moved far from home, and so rather than take it on myself, I came to the place where I stopped sailing. That was probably 20 years ago.

But I took some major life lessons from my years of learning and sailing.

One, and maybe the most important, is not to let my first failure, no matter how spectacular (imagine my six year old self climbing that mast in sheer terror.), stop me. I have a long history of success. I also have a long history of failure before that success. I am not saying you keep pounding you head against the wall in failure after failure, but don’t let one failure or a couple define your relationship with what you dream of doing or being. If had allowed that to happen, I would have missed some of the best things, some of the biggest successes of my entire life.

The second, and this is one I have to revisit sometimes, is that life is not meant to be smooth sailing. It is like the wild wind with choppy waters as much as it is about the placid waters. Don’t get me wrong. I LOVE the placid waters of my life. Truely. I would love life to be that way all the time. But it isn’t. So I had to grow to love the choppy waters and wild wind, and appreciate the exhilaration of navigating the storms. I generally hate the storm when it begins, but by the time I am part way through, to the end, I end up excited, lifted up, reveling in my ability to get through it all.

And third, when the wind changes, it doesn’t mean you can’t get to where you want. You just have to shift the path. Sailing is wierd. You set your course based on wind and currents. Then they shift. And you shift. It’s a dance. It always takes longer than in a motorboat where you just aim, put the throttle down and go. Not so in a sailboat. You shift. You tack (a back and forth maneuver you use when the wind is against you. It takes you forever, but it gets you there when the wind is not co-operating.)

I am in a sailing place in my life. I have been for the past couple of years. It is not what I would have chosen for myself. Frankly, part of me wishes life was more like a motorboat. I an acutely aware of having only so much time left in my life.). But life is not that way. It has been choppy seas and shifting winds. And I am just getting to the place where the lessons of sailing that I learned young, are coming back to me.

I always was a slow learner.

Be well. Travel wisely,

Tom