I was sailing engineless down the northeast coast in winter when my grandfather was put on hospice. I knew he’d want me to keep going with my sailing hustle…
My grandfather was an OG hustler. It’s where I got it from. He could sell literal ideas. His first self directed gig was during the Great Depression as a kid in Brooklyn. His grandmother ran a card room and he would sit under the table with his little brother, Donnie, and collect any chips that were dropped. During adolescence, he kept some raw dough in his pocket from the neighboring bakery and sold “feels” to his schoolmates. The claim? They felt like tits.
His father, Irving, spent too much time at the races and later his brother would join him there–meanwhile the three of them were supposed to be running a family business and my grandmother was pregnant still back in Germany. My grandma kept my pop’s shoes as a promise that he would come back. They met after she had escaped communist Germany and made it into Berlin. He was stationed there in the Air Force. My grandma was working as a cocktail waitress and didn’t know English, but pop knew some German.
Pop’s job in the service at that time was in the mailroom. He would take the train to France and bring back hashish and then push it to his comrades through the internal mail delivery system. “He was like the mayor,” my grandma said.
Back in the states now with his young family, he worked for Kraft Foods. Driving the company car one time on the famous Tappan Ze Bridge overlooking New York City, he crashed. It almost all ended right there.
He told me once that the pressure from all the hustle, after all that time, made him an angry man. And that he let that anger smolder for years until something inside of him had to change. And it did. Though he was never perfect, nor did he claim to be.
Later, he moved on to sell insurance. And eventually, industrial supplies. Which would drive him into retirement, on a mountain, where he lived the life of a yogi and died a legend.
*some details in this story may be incomplete*
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My sailing trip is now basically over. I said I wanted to test the boat in the harshest conditions both she and I could handle coastal, in winter, to see what we were capable of. I lived on the edges of the sea and my nervous system for seven months exploring from Maine to Maryland. I never had a plan. The boat was completely unfinished and barely hospitable. It was very cold. I was practicing seafaring. She was half seaworthy half dilapidated.
Things were starting to get to me under the current conditions, but it always all seemed to work out in the end. The boat and I came right up on our edge—of heavy weather, and I of my own mind.
Suddenly I more or less now know what my days will look like. I have a plan. My work is steady, the boat patiently waits for her refit which I can now slowly begin. The amenities are plentiful. The people are, fine. And yet I can’t help but feel like I’ve lost something.
Magic.
For a while everything was really magical. All my dreams were coming true. There were ups and downs but overall, I felt this cosmic thread connecting my every move towards something larger and greater than myself. I was on the right path with my single handing, my career, my personal life and relationships. And everything around me physically reflected that.
This mindset took a long time to achieve and has not been without its regressions. In an attempt to break from self destructive tendencies and crippling self doubt I put notes all over the hull of my new boat with positive affirmations and coping mechanisms, to gain control of my mind and life.
It worked. But did it go too far?
One of the notes read: “Believe in yourself so much they think you are delusional.”
When you continuously have fated, innately romantic and profoundly passionate experiences in regard to every single facet of your life you start to wonder if perhaps the depth of your being and feeling is not magic at all, but a fault in your own wiring that makes you unfit for modern society and relationships.
I’ve often asked the question: do two people fall in love, or does love already exist and two people fall into it? This is a matter of idealism vs. materialism. In philosophy, idealism states that ideas create your material reality. In materialism it’s the material reality that creates ideas.
I am at odds with the material world.
This was apparent when I sailed my unfinished boat and paddled a poorly repaired kayak alone through New York City. Staring at the buildings with a pink sunset and the ocean in front of me it truly baffled me how I was literally the only one out there out of all those millions.
Soul mates. Death pacts. Planets and stars aligned. Astrology. Tarot. Sea witchery. I believed that all my boats had lead me here to this current boat and was symbolic of the spirit of sailing and adventure. That I’d done well in my travels. My dead friends were living on everywhere around me; In my books they gave me, the money they left me, the sea, and through smell. My living friends were serving as inspiration. I felt that despite my mistakes and wrong turns or perceived losses at the times—they all needed to happen so I could be as solid and focused on the dream and goal as I now am. Or, was…
“Do other people just not get to have this?” I asked my old friend Capt. Dan who was the first person to teach me about engineless sailing. “Not only do they not experience it, but they don’t even know it exists.”
I was this close to signing up for a subscription based predictive astrology service. Everything was meant to be and I was moving along with my life’s plans. And then I made a terrible mistake. I started researching. Scientifically, magic doesn’t exist. Only the mind’s ability to believe and perceive it. Science calls this magical thinking vs. the belief in magic. Magical thinking is more of an evolutionary adaptation of the human brain, perhaps in order to survive trying times… Magical thinking is proven to have cognitive and creative benefits. The actual belief in magic, however, has real world implication and historically lead people to cult like and political terrorist behavior, as well as isolation and individualism.
It seems I had fallen into a bit of a rabbit hole.
In one study they used questions such as “to what extent does the ocean have consciousness,” as a quantitative element of how to measure magical belief. It’s no wonder I got swept away living so close to the sea. It’s the only way I know how to survive. If you take away my belief or faith in a person, or a boat, or myself —it stops existing. So who is to say magic doesn’t exist, so much as I’m the one in control of its existence?
I’ve always said that boats are greater than the sum of their parts. How something so simple can be capable of driving something so complex— an adventure through the natural, social, and inner world. Maybe that’s why I do it, because the sea is closest thing to magic I could find.
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‘Sail it ‘til it sinks.” Said Tom the brewer with the beautiful wooden boat from 1937. I’m more like sail it to the islands and abandon or sell it for really cheap somewhere else. He shrugs his shoulders and takes a sip of his beer before he walks away. He thinks I need to touch up the paint on the hull, but to make sure it matches otherwise I’m going to have to re paint the whole thing. That I need to scrub my teak with a green scrub pad. And he’s going to bring over some rust off spray to get the stains off my deck. He thinks it’s more important I clean my teak then fix the leaks.
“If it’s leaking on your head just move over,” he said.
I’m half rolling my eyes half listening intently. I plan to take his advice. On a boat, some day, but probably not this one. I was going to do a little cosmetic stuff anyway, I’m literally patching this thing together. This boat. I don’t know really what else to do at this point. I don’t want this to turn into a two year project with brand new awl grip paint on deck and topsides. Bright varnish. Perfectly pressed on tell tales. That’s not what this boat is. At least, not right now.
I like Tom. I figured he thought I was a degenerate making myself look bad with my sloppy finish work. But it was quite the opposite. “I’ve got something for you,” he said one day and handed me two picture books; one on the stars and the other on marlinspike craftsmanship (subtle, Tom).
“Wow, I’m honored,” I said. “I always thought you were ashamed of me.”
“Ashamed of you?” He said laughing in disbelief. “I admire you!”
Sometimes everything is such a chore. I feel like a pirate amongst the royal fleet. But then, I’m sitting on the dog house fiberglassing some free scrap plywood I got from the shop, drilling holes with borrowed drill bits, sitting under a makeshift sun shade, with the perfect afternoon sea breeze and the boats just tugging lightly at the pilings. And I’ve got the same view as the million dollar yachts.
