Sterling Hayden was a good actor. Who can forget his mad air force general muttering about precious bodily fluids while orchestrating the end of the world in Dr. Strangelove?
He was a sailor. Perhaps the quintessential American Twentieth Century sailor. He provided the model so many have aspired to. He was the creative spirit, wild and untamed, who did what he had to do to pay the bills and then run off to sea every chance he could. There was a lot to admire in him. He was the kind of “star” we could relate to in our own fantasies,
“If fame falls on me, Oh! If I could handle it like Sterling Hayden!”
That dream, over the years grew increasingly creaky. From the 1960s to the 1980s the face of adventure sailing morphed from the likes of Sterling Hayden to Jimmy Buffett. The dream co-opted into a “lifestyle.” It became a “brand” surrounded by other brands. One could buy it piecemeal, or packaged, with an endorsement from a rum company and franchise outlets anywhere
We are in a hangover from this period. It hurts. But, it also helps us put the past into a new perspective. It reveals a new challenge, How can we do more with less?
How we approach this question matters. If we remain uncritically wrapped-up in a culture that looks at us as a predator looks at its prey we will continue to push on, doubling-down, chasing “efficiencies” more deeply mired with every effort. But, if we approach the challenge of doing more with less as an opportunity to discover what matters, we can bend our efforts and reshape our habits-of-desire, bringing the discovery of meaning into the center of our lives.
No matter how “cool” the icons of the Twentieth Century might have been, their lives were a chronicle of failure and despair. It’s not at all surprising. Even Sterling Hayden split his life between a despised career and a desired avocation. No matter how well he might handle each part, when every effort is split and broken, the whole does not cohere. Our efforts degrade into an insistence to impose our will on reality. We strive to conquer balance, when balance can only emerge from coherence. It cannot be manufactured out of shattered fragments.

There’s an ambivalence at the heart of my relationship with yachting. On many levels it celebrates everything divisive and destructive within our culture of accumulation. But at the same time, yachting has sheltered great value and meaning right at the heart of its showroom-lit darkness. Without this haven for fundamental knowledge and a community of practice – these avenues for wisdom – would have disappeared from memory.
This is why I have pursued the essence of boats for my entire life, against every reasonable, rational judgement. Boats have not made my “fortune” nor showered me with the trappings of success. It’s been mostly contrary currents and adverse winds. I’ve probably confused more than I’ve “enlightened.” What all I’ve been up to adds up to has been as hard for me to decipher at times as it must be for anyone looking in.
We shy from ambivalence. We forget that it provides access to paradox. It’s an open door, a refusal to accept that whatever seems broken will always remain that way. I find myself looking for a transition, for a way out of disintegration and imbalance. Boats are pivotal for me and I’m discovering it is for others, as well. I have a seasoned conviction of the value of boats. They are conduits of meaning. This goes well beyond escape.
We can benefit from examining the pitfalls of our expectations. We can wrinkle something important by challenging the habits of mind we’ve inherited. We can learn from how these paths have closed and been co-opted.
No wonder S.V. Jimmy Buffett sailed on a tequila sea! How else could we continue to believe there was anything left to find, chasing manufactured dreams across barren seas on vessels designed to take advantage of us. The business of escape is a trap. Sterling Hayden recognized this even as he longed to escape his day-job in the heart of the industry of escapism.
As “jobs” sink out from under us, we have no choice but to look elsewhere for meaningful, integrated lives. Boats – totems we’ve been conditioned to see merely as vessels of escape – can reintroduce us to purposefulness. Tugging on our imaginations, they may carry us there. We are poised to unravel the paradox of “pleasure” boats leading us beyond “happiness” to the enduring satisfaction of an integrated life.
Let’s look at how we might integrate boats into living instead of relegating them to escape. In rejecting this worn-out expectation, we might find that boats can be true vessels of transformation.
The first step is to let go of the primacy of desire, as though what we wish for is more important than what is essential. Bending to meet this challenge requires discipline, but the glimmers of value and meaning we discover give us the courage to adapt our responses. The prison of false security is barred by our insistence to follow ill-considered desires.
Let’s leave these hangovers of “Margarita-ville” behind! Let us strengthen our powers of imagination. Life is too valuable to surrender to hollow dreams of escape.
Join us as a contributing author!
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Contributing Authors:
- Antonio Dias
- horizonandpointofview
- Christian
- lloydfeinberg
- thomarm