Sailing Lessons and Tying Knots

A month came and went, and I was so caught up in work and the sailing lessons I was taking at Portland Sailing Center that I neglected to write about all that was happening.

I loved every second of my sailing lessons. The first couple lessons we struggled with wind, with conditions on the first lesson getting up to about five knots at its highest, and on the second lesson I'm not sure it broke above three. But this was a great time to learn many of the basics.

The eventual goal of all of this is to sell everything that doesn't fit on my boat and live on it full time. I hope to sustain myself by living simply and doing things I love doing: writing, making videos and photographs, documenting, sharing, and educating people on this lifestyle change, sharing the stories of others taking on similar life changes. In some ways it feels crazy, if not deluded. What business do I have living like that? Put your head down and keep going just like everyone else. But to me that feels crazy. I could buy a boat that would be my home on the sea for the same price as a very modest down payment on a very modest house in Portland, and then spend the next 20 years of my life paying it off. I watch a lot of Youtube channels on people who have taken similar paths, and on basically every video, there is someone in their late 50s, 60s, or 70s saying "I had a dream like that once. Never ended up doing it." Some are lamenting spending their youth on something else, and others are just happy that they can experience, if vicariously, the adventurous life of someone else. I don't want to be sitting on the other side of my life wishing I had taken this slightly crazy idea and run with it.

Tying Knots

I knew going in that tying knots would be challenging for me. For whatever reason, I have an incredibly hard time memorizing knots. I remember as a young child struggling with tying my shoes (I often chose velcro or slip-on shoes because of this) and later having the hardest time with my knot tying merit badge. But that's also one of the reasons I wanted to take lessons, and to take up sailing in general:

I want to challenge myself to take on things that may not come the most natural to me. The lifestyle I want to pivot to is one of sustainability and self-sufficiency, and as much as I'd like to think my lifestyle now promotes those things, I know it is not the case.

Closing the Loop

I don't live lavishly in almost any aspect of my life (at least in relative terms for when and where I live), but I know my impact is still immense. This is as much (or more) a systemic problem as it is a personal one, as was beautifully commented on by Mike Rugnetta on his podcast Reasonably Sound. Of course the open water, gorgeous beaches, and copious sunlight of the Bahamas calls to me, and certainly makes for a idyllic lifestyle goal, but so too does lessening my reliance on plastic, fossil fuels, and opting out of a system that is completely untennable.

So, what does that have to do with tying knots? Well, to me it's about the challenge. It's about seeing myself in a new light, it's about picking up skills that have always daunted me, and made me feel like I'm fundamentally incompetant at certain kinds of tasks. It's about creating a closed-loop home, where the very fact of me living my daily life does not put the planet in peril, while simultaneously being able to take control of my own personal destiny in a more direct way than I would be able to on land continuing on my present course.

The Secret to the Bowline

The bowline was the hardest knot for me to memorize (though even last week I tied granny knots instead of square knots! Darn!), but there's a secret! Just make a lower case "b" with the first loop (not a "d", it will be backwards), then through the b, back around the stem of your rope, back through the same "b" loop, and snug it tight! Flawless bowline every time.

How to Tie a Bowline


I love these simple tricks that make something that feels endlessly challenging feel like a piece of cake.

Learning to Sail

Alright, this is the beginning! On Tuesday, August 4, 2019 I'll be one (small) step closer to... well what exactly? Let's go back a bit. I've always been drawn to the ocean, and telling a bit about that story is what this post is about. Setting the scene for what I hope will be an interesting story of learning to sail, buying and living on a boat, and the explorations and realizations that would certainly come from such a transformation. Or, at the very least, what comes from diving into that world.

But let's start at the beginning. I was raised in Salt Lake City, Utah, which, despite being named after a body of water, is quite a dry place. Even the lake for which it's named feels desiccated.

The Great Salt Lake

The Great Salt Lake. Source: USGS

Every year as a child, I would look forward to our families' annual trips to Balboa Island, near Newport Beach, California. This was a tradition that my extended family held for at least two generations, and unequivocally the highlight of my year. The salty breeze, the cycle of the tides, long days in the sun, sand castles. Frozen bananas from Dad's never hurt, either.

Source: Visit Newport Beach

The best, however, was always the day (or two, if I could convince my family to dedicate another day to it) was boogie boarding at Carona Del Mar. They don't allow stand-up surfing, too many people and relatively small waves, but I got absolutely hooked on catching waves there with my little boogie board. I would stay out all day, only coming back for the odd rice crispy treat. This was truly a day I would look forward to the other 364 days out of the year.

Source: Orange County Archives

Source: Wikimapia

It goes without saying that going to Balboa for a week or two at a time was an immense privilege. In fact, the increasing struggle that going to Balboa became for my family was a lesson for a young me in what privilege and wealth actually meant. We had been going there from when I was born, so it was something we just did. My grandfather was a law professor, my dad worked in Silicon Valley, my uncle made it rich in the dot com boom. Things fall apart, however, and for many reasons that are far beyond the scope of this post, we weren't able to go around the time I turned 15.

Those times that we had are precious to me, and beyond that, they taught me about myself and my love for the ocean. Part of my desire to move to Portland five years ago was to be closer to the ocean. And in the back of my mind, learning to surf and learning to sail were things I wanted to accomplish out here on the west coast.

Some dreams take a long time to realize, and I can't wait for Tuesday.



“Begin at the beginning, and go on till you come to the end: then stop.”