Pass Over

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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When things went south

MY BRAINHere is a look into my mind, from when I first really decided I needed to have a boat of my own. Perhaps it was decided for me. Nevertheless, here is an excerpt from a letter I wrote a friend while I was sailing around British Columbia this summer aboard a man’s boat whom we will call Jack, as in captain Jack (obviously). This friend and I met while we were living and working together on a farm in the foothills of Mount Rainier.

I just walked through a forest trail that had this plant with leaves the size of my body. Where I came out on the other end was this really shitty looking diner, but inside is the most wonderful robins egg blue walls and tables, with all natural light from the big open windows. I’m in Pendar Harbor, BC. There are so many places I’ve visited on this sailing trip through Canada where I’ve been like, “Why can’t I be half Canadian?” Which is funny because I’ve been thinking a lot about getting my own boat, having my own piece of the pie. Jack’s extensive resume of small, attainable boats has me itching to try it on my own. It’s more of an obsession really. 

There’s this story of a man, middle aged, he’s a filmmaker and has this small boat and all he can think about is sailing it around the world alone. In his documentary of the solo voyage, where he loses his mast and experiences an incredible torment of large, breaking seas and relentless gale force winds, he says “If I wasn’t here, I’d probably still be thinking about it.” Boats can borderline obsession and I wonder, if I stay aboard Jack’s beautiful, perfectly maintained cutter– will I still be sitting there thinking about my own? 

I love Jack and every time I lay down in the v-berth, my head tucked into his armpit, warm light pouring through the open hatch I think “this is perfect, how could I want anything else?” But within minutes of every hour, the thoughts creep back in. Scheming how I can manage to obtain and eat my piece, of the pie, or should I say my “peace.” 
 
On Jack’s boat I’m lazy. I know he is there to keep me safe and I put in minimal effort. I think back to the farm, when my days were so full. I feel like my hands and head were always busy. On my own boat, I imagine it would be similar. I’d be responsible for keeping the farm floating. Yet there’s something inherently isolating about being a sailor, living on a boat. And Jack, who has had partners on boats and been solo, is one of many who says solo sailing sucks. Maintaining a boat alone sucks. Living on a boat alone sucks. But do I perhaps needs to figure that out for myself? Will leaving this boat be one I will always live to regret? Will a boat of my own be my white whale? Something that will swallow me alive financially, emotionally, physically? Do I owe it to myself to figure that out?