Being bad at something feels bad. Maybe that’s why as we age we lean into things we’re familiar with and good at, so we feel comfortable and appear cool. Challenge isn’t always welcome. As one of my charter guests once summed up, “I’m too old to suck at something.”
My own introduction to sailing was a disaster. I flipped a Lido dinghy, which then turtled (mast in the mud), and it took four tries to right it without dunking myself again. I got back to the dock cold, exhausted, and looking much worse for the wear. I definitely sucked at my first try, but I was hooked. Sailing was a whole new world and damn it, I was going to master this thing.
Fast forward a few decades, and although the disasters are fewer, I’m still trying to figure things out between dialing in sail trim, deciding on rough weather tactics, perfectly flaking a sail on the boom, or even keeping a fridge going on a boat with worn out batteries. Sometimes I wonder exactly when I’ll learn all there is to know about sailing, but the truth is there are no shortcuts. I love when people sum up their sailing experience with statements like, “And that was the weekend when I learned to sail,” as if that’s all it takes. Most of us need years to master something. The process can be unpleasant and embarrassing—and as we grow older, the various insults of aging are mortifying enough. Who needs more?
Sometimes I think, “Seriously, why am I doing this?” And then I answer my own question: Because I’m better for it. Although learning is tricky and makes me wonder why I’m willing to look uncool and rack up the boat bite bruises, it opens my horizons and changes my world.
I’ve found that learning new stuff is better when shared. I love to watch people get the hang of steering a straight course or moving through the perfect tack. Faces light up when the chartplotter begins to make sense, when a knot is tied correctly, or when a mooring ball is caught on the first try. It feels like accomplishment, and we humans are built for challenge. Without it, we wither.
It’s too easy to stop growing and give into complacency just for the sake of not looking foolish. Sometimes it takes distraction to ease the pain of incompetence, and I’ve found that games or shaking things up with a twist on the traditional classroom helps. I’ve been known to offer up the “chick and dude sail” to break up couples’ roles and have women sail one leg while the guys make lunch and then switch. And using the boom as a long whiteboard to diagram a class on sailing basics is always entertaining enough to forget the discomfort of not understanding something new. It’s the spoonful of sugar that makes the medicine of unfamiliar adventures go down easier, and it distracts from feeling self-conscious as we trip and stumble our way through growth.
When was the last time you had fun learning? For me, every day on the water is an opportunity to stretch and enjoy, and if I’m lucky, I’ll learn some sort of lesson that I’ll actually survive. Sailing has a way of making my life bigger, and that’s worth more than anything some humiliation can dish up. So what if the jib is flapping or I forgot to pull up the fenders as I exit the marina? I’m out there and not the least bit worried that I’m too old to suck at something.
June/July 2025
