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.