Casting my fate to the wind I confronted the last most credible year of my life— I had turned out to be a 29-year-old cornered by a demanding profession, the quest to find success in show business had left all matters large and small, both onstage and off devoured by the rapacious appetite of my most insecure self. Drowning in my own shallowness turned into trying to repurpose my time— I tossed a life preserver to my foundering soul and signed up for sailing lessons. I had no clue if this was even something I would like.

Lessons were taught in a classroom and on an 18’ sloop rigged keelboat. After passing all the tests both on the water and off, I was qualified to charter a boat— I could go sailing on my own. Sailing solo seemed to matter— listening to the wind, feeling the direction of the breeze on my ears, making visceral contact, relearning how to be present without suffocating my feelings with words— to see and sail by my wits with the wind. 

Sailing on the Oakland Estuary, this was where the new sailor practiced. There was no plan to do anything more. There was no motor, no running lights, no electronics, no accommodations for eating or sleeping— there was just a boat and water, wind and sail, and this fragile younger newly minted beginner trying to reintroduce himself to the missing person I had become.

Until I’d taken lessons skilled sailors aboard larger sailboats had not attracted my attention— I’d hardly taken notice, my curiosity had gone missing. 

In 1980 the Nordic Folkboat was a common sight on the San Francisco Bay. Fashioned of wood, 24 feet in length, the hull was constructed by lapstrake planking, the cockpit was an open design and the sailor sat low to the water— it was an advantaged position from where the helmsman could read firsthand how the boat was working with the wind and water.

Racing had no appeal, what I liked most was knocking about on my own terms without a care, playing with whatever wind and sea state I might encounter. The sage Folkboat helmsmen wore khaki— pants, shirt, and cap— khaki was the rule. In 1980 aviator style sunglasses were fashionable among this group. If a jacket was needed men would wear barn coats fashioned of waxed canvas with chocolate corduroy collars. 

Not ready to toss my youth away I resisted the khaki sheik raging fashion of the time. Polyester was only in its infancy, but brighter colors and tighter stretchier fabric was easier to move around on while sailing in a cramped cockpit. All these choices— what to wear, what sunglasses to sport, all was subliminal— I wasn’t going GQ so much as unwilling to toss my youth away and join the khaki craze— it would have been a uniform indicating I’d become a member of the Sears & Roebuck house of worship, — cementing my sobriety and celibacy to a fateful unquenched misery.

The socially in the know sailor is by nature smitten with the fine figured opposites found sipping white wine along the waterfront cafés. Among the vital maneuvers even a beginner sailor can refine is the nonchalant docking of a boat near such a drinking establishment so that you might pause to go fishing for the love and affection that incessantly goes missing in a boatman’s life. There is no such thing as luring a sullen moody above the fray catch while clad in khaki— this is as true now as it was then, it is this invincible khaki clad cotton constructed barrier to a more amorous life that must be avoided lest you toss away all hope of finding what instinct insists you must have in abundance. 

Beer drinking on hot days— when one arrives after sailing the helmsman and crew will regal the day’s romp on the water. A thirty-something anoints the end of a sail with beer brewed bravado— these are peak experiences— no other cohort of desperate lads can mount a more well played winding down of the day. Distracted, suffering from a lack of affection and then once sated the landlocked misunderstood mariner returns first to the sea and then the saloon. Heartbreak runs rampant among this kind.

By 2001 my footing straddled both sides of my aging self. I could still finish off the day buying a round in a pub, but the lines controlling both a boat’s sails and a man’s interior tethers were afoot. My sailing skills had advanced— the newcomer to the sport was no more.

Not appreciating the magnitude of the task, with a kind of blithering innocence I undertook the task of fully restoring a derelict wooden sloop. Between 2001-2007 I made seaworthy a 25’ sailboat— the class of boat was named the Golden Gate. Not only had I the pleasure of knowing every fastener, every board, every piece of bronze I had also sparked the unanticipated deeper cultivation of pieces of my most difficult to repair character. From the boatyard where I would labor, I developed my focusing skills, breaking tasks into incremental pieces— fix one thing then the next— doing whatever is required for as long as it takes— getting it right was more of the point than the time it excised from my charade filled exploits as a land-loving sunburnt Romeo of a kind. Fixing a wood boat with tools and by hand had moved both man and his future forward— fixing the boat had indeed also help fix this sailor.

My wooden sloop had been owned by the bass player for Huey Lewis and the News. Even prior to this glancing blow with rock and roll fame several other owners had sailed this boat to best boat of the year and season’s championships. Built in Sausalito in 1959 Maestro had earned much notoriety as one of the swiftest of all the 17 Golden Gate’s ever to sail on the bay. Flush decked this is a sailor’s sailboat— her personality on the water and in the wind marked her as one of sailings most capable craft. With the wind in her sails Maestro again and again said to her helmsman that something was right with the world and this right feeling you knew to your core, this boat spoke to you through the varnished tiller in your hands.

I bought her, fixed her, lived on her, sailed her and sold her. Maestro was shipped off to Moss Landing, her new owner would sail from this fishing harbor in Monterey Bay. 

I thought I would hear from Maestro, she was too palpable, so capable, so tangible, my hands were stained with her varnish and paint, blisters on my palms were still healing from the hours of swinging a caulking hammer. After I had dedicated to Maestro my best— just like that she was gone and in her place was fit a new boat— a fresh brand-new uncharted course. This four-decade long boat alliance was far from over, there were still too many lessons to be learned, too many ways I could go lost or be found— a sailboat enables the sailor to remain closer to the interior pieces of his soul, the right boat will share their spirit, you will know your boat and your boat I am convinced will come to know you.