Do you even know how to sail?

March 3, 2021

How to take the first step forward in your dreams

“Do you even know how to sail?”

I was sitting in the open, majestic atrium of the Hyatt Regency Hotel in San Francisco, in the 2nd session with my new life coach, Agathe.

She had asked me probing questions on what I wanted in life, goals, and aspirations. 

I was describing this grandiose vision I'd had since I first heard Jack Sparrow say, "Wherever we want to go, we go. That's what a ship is, you know. It's not just a keel and a hull and sails; that's what a ship needs. Not what a ship is. What the Black Pearl really is, is freedom." That line awoke an awe for sailing in me. I, too, wanted that  freedom. 

Amerigo Vespucci

I'd read stories of the expeditions of yore. I subscribed to sailing blogs of families living aboard yachts in the Caribbean. I’d consume their tales of catching Mahi Mahi off the back off the boat, tasting the freedom through their words. 

In my dream, I’d get my boat later in life. I’d work my career, get rich, then buy a huge ship like Jack’s Black Pearl and sail it around the world with a crew. 

As I was telling Agathe of this majestic vision I had for my future, she sipped her stone ceramic mug of passable coffee and calmly questioned

“Do you even know how to sail?” 

Her words hung in the thousands of square feet of empty space of the Hyatt’s atrium.

I took a deep breath, and in an instant realizing how stupid my vision was, mumbled “no”.

She took another slow sip, and her next words set me on a path that has led to one of my greatest joys.

“Why don’t you start there?”

I immediately launched into finding any way I could get my ass on a boat in the next few weeks. I looked at sailing classes, but they were thousands of dollars, and I was early in my career. That wasn't an option.

Some sailors in a forum mentioned trolling the docks and trying to help out the boat owners. I made my way down to the Marina full of enthusiasm and met a wall of locked gates.  

I stood there staring at the locked gates in defeat, feeling naive.

There’s no way I was talking myself onto a boat like this, in a different city, perhaps, but not in San Francisco.  This wasn’t the key to getting on a boat.

Sailing with internet strangers

Given that one of the fastest ways to meet people in the tech industry in San Francisco is through Meetups, I decided on a whim to see what was there.  

I sat down and logged on to and put in the word “sailing” within 25 miles of SF and found this

After clicking through the different listing and upcoming events I couldn’t believe it. There were boat owners that went out sailing on the bay with internet strangers just to have extra crew. 

With a few clicks I signed up for an upcoming sail with Richard on his 30ft Catalina sloop, Olenka, sailing out of the Berkeley Marina.

I was tense with nervous excitement the whole week. I had never been on a sailboat. I didn’t want to appear so inexperienced, so I found an intro to sailing documentary on Amazon Prime and devoured it, eagerly taking notes.  

When I got on Richard’s boat there were so many ropes, and cranks, and thingies, it was overwhelming. As soon as we were underway on the Olenka, out on the water under sail, I was surprised by the silence. We’re accustomed to a lifetime of combustion engines moving us around noisily. Only the lap of water against the bow, the wind on your face, and the slow change of the horizon tell you that you’re moving on a sailboat. The world falls quiet. I was enthralled. 

We sailed through the Bay across the face of the city and under the Golden Gate Bridge. Just as the boat passed under the bridge the crew whooped and their voices echoed off the bottom of the bridge. In that moment, on the Olenka with a bunch of internet strangers, I knew I had been right about my vision. Maybe the details would change, but being on the water under sail spoke to my soul. I had found the first key. 

Salty Hippies

The next key to my journey arrived the same day as my first.

Richard pointed me towards Cal Sailing Club, also in the Berkeley Marina. As soon as I got home I found their website and signed up. For $90 per quarter I could get unlimited time on the water.

Cal Sailing Club spun out of UC Berkeley in 1979, but it still has the feel of a shitty frat club in all the glory that shitty frat clubs have. The tattered couches in the hangout area were likely found in an alley, but the boats were well maintained. The people were alive with a zeal for the wind. 

All that summer I spent Saturday mornings on their 15 foot Bahia dinghies. 

This crazy, fratty, hippy sailing co-op gave me the skills to sail, my second key. 

The Surprise Sailor

The last key came while sitting in a meeting for the nonprofit I was on the board of. We met regularly on Monday nights at Church Street Café. Without fail, Howard was always there. Howard embodied San Francisco activism. He came to San Francisco in the 60s, fell in love with the city, the bay, the people, and never left. He was our most loyal member. 

By this point in my sailing journey I’d already known Howard for more than a year and never knew he was a sailor. That Monday night he mentioned that he’d just been out sailing over the weekend on his boat. 

“Howard, you have a boat? Can I go with you next time?” 

Howard took me on a sail with his sailing partners, George and Matt, on The Red Baron - the perfect day cruiser. The Red Baron is a vintage Cal 20 that Howard’s kept on the bay since shortly after he got there in the 60s. They explained to me that many boat owners are actually fractional owners and go in on a boat together. On the Baron there were 4 partners including Howard. 

As luck would have it within a few months of that first trip their 4th partner left the Bay Area and I took his place on The Red Baron.

manning the tiller of The Red Baron

The main cost of partnership was the slip fee, my share was only $175 every 3 months. There were occasional repairs, new ropes to buy, and whatnot. The largest payment I made was a little over a grand when we hauled the boat out to do a bottom job. Only once in the roughly 4 and half years I sailed on The Red Baron did we need to do that. 

Averaged out over the years I spent $100 dollars a month for a nice little boat. For the price of a nice dinner or a monthly cable package I was fulfilling my dreams. I even had my very own key to the Marina gate. 


A few weeks ago I moved to San Diego and gave up my partnership on The Red Baron. I went on one last sail together with one of the partners, Matt, and soaked up the experience. The smell of the sea, the taste of salt in the air, the worn smooth wood of the tiller in my hand. After we got back to the docks and took the sails down I gave Matt the key to the Marina gate. I felt a real sense of loss, that same warm sadness you feel when a friend moves away. 

As soon as I got home after that last sail I began researching San Diego's sailing scene. Low and behold, there's a group called Convair Sailing Club that looks like a nicer version of my old friends in Berkeley. I've got the next key. 

It’s been almost 5 years now since I had coffee with Agathe in the Hyatt. I remember that moment, when the entire atrium filled with her question, “do you even know how to sail?” and I laugh. I've come such a long way. I can't imagine buying a tall ship and sailing around the world with a crew. But, I've come so much further than if I'd kept that vision just a dream. 

Whatever your crazy dreams and grandiose visions, I promise you there are internet strangers, salty hippies, and old sailors that can help you unlock them. And so I'll ask you, 

Do you even know how to sail?

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