Chapter 3 - Becoming a Teacher

 The impetus to circumnavigate came in part as result of being repeatedly asked where I lived. Upon first becoming a sailing instructor I taught in San Juan Islands and Seattle and my response to where I lived was always Seattle. This wasn't entirely true because after separating from Diana and moving back to Seattle from Eugene, I never got an apartment or house. I just house sat and stayed with friends when I wasn't on the water teaching.


As soon as I had registered for the instructor classes and coast guard certification in December 2021, San Juan Sailing booked me for 10-12 weeks of sailing instruction. I was so excited -- I had not even taken the courses or passed any exams. This was purely based on my relationship with San Juan Sailing over the years as a charter guest and owner -- note to self about maintaining relationships and not burning bridges. And yet this excitement was familiar -- it was the same feeling I had when I arrived in Fishkill almost 40 years ago, that there was something else at play here.

The spring and summer teaching as a new instructor in the San Juan Islands and Seattle was absolutely magical, for a variety of reasons. I wanted to hone my craft as a sailor and teacher and immersion had always worked for me as a way to build skills and confidence. I said yes to everything. I was teaching week long courses at San Juan Sailing and as much as I was teaching, I signed up to teach day courses at the Seattle Sailing Club in Shillshole Marine during my weeks off. Teaching a few days a year there gave me access to a fleet of small boats (that easily get overpowered)  and I wanted that different experience. Ok, my Jewish heritage was coming through and I also wanted to make a little extra money.

Prior to teaching for a school, ASA requires that one do a "ride-along" with another instructor, watching and learning how they teach the course.

At San Juan Sailing I did my ride-along for a week in April with Bob Hulette, and ASA instructor of the year. Bob is not only a very accomplished sailor, but an amazing teacher. I was so honored to have him as my first real mentor and learn by watching him usher students in a weeks time from no experience sailing to qualified skippers that could charter their own boats. April can be sporty in the the San Juans, and we had an exemplary week of that, the winds constantly blowing at 25-30 knots.

I had a similar experience with my ride-along at the Seattle Sailing Club with Steve Summers. Steve had been teaching for 40 years as a NOLS and Outward Bound instructor, really dedicated to craft of using the environment to transform youth into adults. I'll never forget what he told me about keeping teaching fun by viewing classes not as teaching the same material over and over. Instead, first being curious about what my students know and or don't know, and how they learn. With that mindset every class is a new beginning.

As I taught each class, I slowly started to understand what it really means to be a teacher. All my life I had been a problem solver, and dedicated myself obtaining more knowledge and skill that allow me to solve bigger and more complex problems. Now as a teacher, one only has to have slightly more knowledge than the students, and instead focus on how to impart that knowledge. This was a huge revelation to me, and still is to this day.

As the spring and summer wore on, plans materialized such that I could continue teaching in other places when the season ended in the Pacific Northwest (PNW) sometime in mid October. In February 2022, months before I receiving my instructor certifications, I had started investigating what it would be like to teach in other locals. As much as I loved the PNW, I really had no reason to stick around for the rainy season, at least not all of it. ASA (American Sailing Association through which I was getting my instructor certifications) has a site called "Schools Seeking Instructors" and I contacted a number of them. Two of them got back to me pretty quickly, one in Grenada and the other in La Paz, Baja Mexico. I was up front with them about my sailing experience being a new instructor. More on the incredible students I met and iconic experiences of that spring and summer later.

As September rolled around, the first trip out of the familiar cruising grounds of the PNW was to Greece and the Ionian Sea. This was a pleasure trip that originally been planned in 2020 but got postponed due to Covid for two years. Confidence generated from sailing in familiar waters gets exposed when cruising to new destinations. The initial couple anchorages overcame that anxiety and we had a great time. At some point I'll include a whole chapter on the three week trip from Corfu, including a week on land exploring the back roads in a Fiat.

After that trip I came back to Seattle -- with Covid no less -- and spent two weeks recovering and getting ready for a month in Grenada. This was going to be my first time in the Caribbean and I was excited to experience the island culture. I did another ride along with another great instructor -- Andy Van Zyll from South Africa -- and realized that I really didn't need to do these any more. The knowledge of new cruising grounds for a week of teaching can be written up in a two page memo and discussed in 30 minutes but the sailing instruction material is the same. It is certainly worth experiencing how another instructor teaches but that isn't worth a week at sea unless we are really co-instructors. I also need to include a chapter on my month in Grenada, the sail training races, Tim’s BBQ, and the amazing instructors I met (Andy, Chris, Miles, Nico, Sara, Yvonne, and James).

Coming to Baja straight from Grenada was an experience in and of itself about which I wrote an entire blog post here - A glass Half Full Day I immediately felt at home in Baja. It isn't overrun with tourist -- as is the case for the places I have been in Greece, Mexico Mainland, and Grenada -- and the locals actually get to participate in the economy here. The other sailing I've done and in most beach cultures I've been to the locals are relegated to serving the tourists as maids, cooks, bar tenders, construction works, etc. They are paid poverty wages and live in slums outside resorts away from the beauty presented in glossy travel brochures. I've longed to experience the culture of host countries like this when traveling for pleasure.

Originally I had planned to do a ride-along for a week upon arrival. But having decided that was not necessary, I took up an invitation to be with some friends in La Ventana for the first week and take kite boarding lessons. La Ventana is my kind of place. Learning to kite board -- or trying -- was hard and humbling. I thought because I know how to sail and understand a bit about the wind, that I would take it up quickly. After a week I was able to fly a kite, but still barely able to get up on the board and drank a lot of sea water trying as I was getting dragged around by the kite. I'll take it up again when there is a lull in my schedule.

The Sea of Cortez around Baja was the third new cruising ground for me in as many months and I have noticed the process get easier with less angst each time. As long as I go through normal checklists, the experiences are always safe and enjoyable for all involved. My long IT career taught me well to be comfortable with being uncomfortable. But the thought of needing the next challenge -- besides becoming a better teacher, a vocation in which I still have a lot to learn -- started percolating to the surface with much more clarity. The next step as a sailor is to live on a boat full time, and instead of getting to all the destinations I still want to sail in by plane which is what I have done until now -- I would have to learn to cross oceans. And as long as one is crossing oceans, one might as well circumnavigate.

Three things scare me in life:

  1. Big seas - this is easy to overcome with knowledge, mentoring and experience. Just takes a little desire.
  2. Being alone.
  3. The fear of getting to the end of my days not having done the things that were really important to me.

One piece of clarity that has come along over time is that life has always worked best for me when taking action towards addressing my fears on a daily basis and figuring out how to build community, companionship, and intimacy along the way. There is a huge fear that if I plan to live on a boat, that I will be doing it without a partner forever. But the reality is that I cannot control a compatible partner coming along and if I wait for that, it may never come to fruition in which case I would still be alone, only sitting on my couch instead of sailing the seas and seeing the world.

The reality of these priorities really hits home when trying to date on land and constantly being asked "where do I live?" Telling people I live in Seattle and will be back in April is a half truth at best -- while I have community there, I don't have a domicile. Further more, the thought about getting an apartment and furnishing it makes me land sick!! Conversely, the thought about living on a boat makes me happy

The other thing I started noticing is how curious and engaged I become with folks that are living on their boat and cruising around the world. This is true of Kevin Connel. I sailed from the Guatemalan border up the coast of Mexico to Puerto Vallarta with Kevin and his crew last year. The learnings about this trip -- and how to feel -- will be in another chapter as well. After I left him in November, he worked on his boat till February and departed for the Marquesas Islands. Since then then he made the additional crossings to French Polynesia, Tahiti, Bora Bora, Fiji and is now in Brisbane, Australia. Shortly he will be departing for Indonesia.

We met an incredible family while we were in Ensenada el Cardonal on Isla Partida. They had a seven year old daughter and sailed straight down to Ensenada from Victoria in September. It took them 14 days without stopping. It turns out she is both claustrophobic and gets sea sick so while they are at sea he has to single hand the boat. She does take her 3-5 hour shift at the helm so he can sleep — how that is managed I’m not sure. How she signed up for this I have no idea but she said she loves the adventure.

They plan on spending a year exploring the Sea of Cortez, getting off the boat a bit, and  taking immersive Spanish classes. Then they will continue their journey around the world and head across the Pacific to French Polynesia, Fiji, Indonesia, etc.

People like this are my tribe and I'm ready to join them. The YouTube channels depicting these stories are engaging and inspiring but the in person meetings really hit home. I’ve watched lots of videos of people sailing around the world, but meeting people in person that are doing it is a very different inspiration. I am always intrigued by their story. It makes me realize I have a next step.

It doesn't really matter how far I get or if I get all the way around. And I'm in no hurry. What matters is the vision generates focus, focus creates presence, and presence creates peace.

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Chapter 4 - Deciding to Cruise

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Rewiring