“Why I Sail,” by Webb Chiles

In this month’s Sightings, Webb Chiles attempts to answer the answerable. Don’t forget that Chiles still regularly posts on his website, which can be found here.

“Those who dance are thought mad by those who cannot hear the music.”

I first came across that expression a few months ago in the opening credits of a movie about mountains and partially about mountain climbing. I have since learned that it is well known and attributed to various sources. The words echo what I have observed in my own life and called the dog- whistle effect. There are those, perhaps many, who simply cannot comprehend my life, just as we cannot hear sounds that dogs can. I have learned that people understand my life and why I sail almost instinctively or they do not and never will, which is one reason I generally deflect the question, “Why do I make my voyages?” Another is that, as a long-ago philosophy major, I came to the conclusion that as a species we have evolved to be fairly good at figuring out “how” — at least some of us have — but not at answering “why?” Western philosophy can be summed up in four words: Good questions. Bad answers.

So when a man in the audience at a recent talk I gave at the Richmond Yacht Club said, “And now for the big question: Why?” I did not attempt to provide an answer. Some, including a Latitude 38 editor who was in the audience that night, subsequently expressed regret that I did not and offered me the opportunity to do so here. Thus I find myself attempting to answer a question I consider unanswerable. This is partially self-serving. I figure that if I write this out now, after it appears in Latitude, I can post it on my website and in the future simply refer anyone who asks the question to the site and never have to answer it again.

Webb Chiles at Richmond Yacht Club at the end of May.
© 2019 Latitude 38 Media LLC / Tim

The question actually has two components: “Why do I go to the edge of human experience?” and, “Why do I sail?” For I could have gone to the edge in other ways.

The very first words of my first book about my first circumnavigation are: “I was born for this moment and all the days ahead.” I believe them to be true, so the most fundamental answer to “why” is that I was born to.

I believe that to survive, our species needs most members to be stable workers and responsible parents, but it also needs to spin off a few who are original experiments destined to explore and expand the edges of human experience. From childhood I have believed I am one of those original experiments, even though aware, as I wrote decades ago, that most original experiments are failures. Whether I have been a successful or failed experiment remains uncertain.

At least partially jokingly, I recently declared myself a success when I learned that one of my aphorisms, “Live passionately even if it kills you, because something is going to kill you anyway,” now appears on tea bag labels, joining my better-known, “A sailor is an artist whose medium is the wind,” which has been used without royalties on T-shirts, coffee cups, paintings, photographs, and even an ad for women’s shoes.  What other sailor do you know whose words are so widely stolen?  What other writer?

If one accepts that I am an original, and a fair number of people have come to that conclusion over the years, then one could reasonably ask, but why sailing? This is easier to answer.

I was born in Saint Louis, Missouri, and raised in a suburb of that city about as far from the ocean as you can get. I was not close to my mother and stepfather and wanted to be as far away from Saint Louis as I could get, so I was overjoyed when in my early teens my grandparents, my father’s mother and her last husband, to whom I was close, retired to a small house three in from the ocean at San Diego’s Mission Beach.  I spent my high school summers with them, and those summers probably saved my life. I was over the seawall and on the beach and in the ocean from morning to night. I saw sailboats pass. I had never sailed. I knew no one who sailed. Sitting there I told myself that one day I would, and obviously I have.

Another teenage moment: I am at a movie theater in Kirkwood, Missouri, watching the mostly forgettable Fire Down Below, starring Rita Hayworth, Jack Lemmon, and Robert Mitchum. There is a scene in which Hayworth goes to the bow of a sailboat anchored just off a white-sand tropical beach and dives gracefully into blue water to swim ashore. A lonely boy, I told myself that someday I would have a boat like that and sail with a woman like that to an island like that. And I have. Many times. It has not all been an ordeal.

I was an only child and it took. A perfect upbringing for a solo sailor. I am not meant to be a team player. I have almost never sailed with anyone except a few of the women in my life.  I have written about entering the monastery of the sea, and though I am a much-married monk, I cherish solitude some of the time and sailing is something I can do alone.

Once when asked what sailing means to me, my instant reply was “freedom.” Part of that freedom is escape from and part is escape to. Escape from the restrictions, regulations, and banal, ubiquitous ugliness of modern urban life. Beauty can be found in cities, but as isolated oases briefly glimpsed between telephone poles, billboards, and graceless buildings.

Escape to a world that is simple, direct, beautiful, uncompromising and unsentimental.

Sailing from the Caribbean to Florida in 2017 — as part of his solo circumnavigation on the Moore 24 Gannet — Chiles had ideal conditions. “During one of the beautiful afternoons I was so happy I took the photo of an old man having fun.”
© 2019 Webb Chiles

The sea is not cruel or merciless. We are. The sea is insensate and indifferent. It is what you make of it and yourself. If a sailor is an artist whose medium is the wind, the sea is the canvas, a still — with some exceptions — pristine canvas, though perhaps not for much longer.

I love the beauty of the open ocean. I love not hearing news of greedy billionaires and the stupidity of self-serving politicians. I love that the only sounds I hear at sea are the wind, the water, and the music I choose to play. I love feeling my boat move in perfect balance through waves. I love having the clear-cut responsibility for myself and my actions.

Long ago I wrote, “Define a man, then, by that against which he must strive.”

When I was young I looked around and saw that the biggest thing on this planet is the ocean. So it has been that against which I have chosen to strive and be defined.

That is perhaps sailing’s greatest freedom of all: the freedom to be myself.

I don’t know if I have answered the question “Why?” but I have done my best, and if you don’t understand now, you never will.

Take a moment. Listen. Do you hear music?

1 Comment

  1. Avatar
    David Hare 9 months ago

    We met forty years ago on my Swan with Gene T. You became my hero and remain so. My life at sea became my livelyhood working up the ladder to Master Unlimited. That meeting with you set a course for my voyage through life. Thank You!
    David Hare

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