The First Time I Felt Joy Doing This
Let me set the scene: a crisp, sea-salted breeze wafting off the Atlantic, the faint cry of gulls overhead, and a creaky wooden dock wobbling beneath my feet. Sounds idyllic, right? Except, in that particular moment, I was hunched over with wind-chapped cheeks, absolutely butchering the task of tying a bowline knot on a sailboat. My father stood nearby, arms crossed, equal parts amused and horrified. "Charlotte," he said with a sigh that carried the weight of several seafaring generations, "if you're going to call yourself a Winslow, you're going to have to get this right.”
For most of my teenage years, sailing felt more like an obligation than a source of joy. It was family currency, as embedded in our legacy as the weathered beams of our Kennebunkport home. Navigating those briny waters with my father or brother at the helm never gave me the thrill it seemed to give them. I was just… there. The Winslow-in-training, a reluctant first mate whose duties mainly involved fetching snacks and enduring sunburn.
That was, until one golden August afternoon when everything changed.
The Day That Tied It All Together (Literally and Figuratively)
It started innocently enough. My parents had assigned me the task of leading a small group of local kids—campers from some nearby summer program—on a "Beginner’s Day on the Bay." Honestly, I think they figured if I couldn't wow my peers with secret knots or dreamy maritime jargon, maybe I’d find an unlikely co-captain among the six-year-olds I was supervising. Lucky for me, it was a quiet day: light breeze, calm seas. No mutiny in sight.
About halfway through, one of the kids, a pint-sized fellow named Theo, asked how to steer the boat toward the lobster buoys dotting the horizon. Rather than call for help, I thought, I’ve got this. What happened over the next hour is something I’ll always remember vividly—not because I was perfect at it, but because, for the first time, I leaned into the fun chaos of it all.
Theo gripped the tiller like it was a joystick in a video game. I gave him simple directions—"a little left, no, your other left!"—and turned the experience into a slightly ridiculous but manageable adventure. The other kids treated every puff of wind like we were seconds from a shipwreck in the Bermuda Triangle. I laughed with them. I stopped trying to craft an experience that fit the perfectionist Winslow ideal and just let the moment happen. Somewhere between answering "What happens if there’s a whale under the boat?" and helping Theo guide us back to shore, I felt something new: joy. Pure, unbridled joy.
What Joy Teaches You About Living
It wasn’t obvious at first, but that day on the bay planted the seed for how I’d approach passion, from relationships to creative work. Here are the lessons I’ve carried forward, tidily wrapped up in a slightly nautical metaphor for good measure:
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It's okay to drift before finding your direction.
Had I decided that sailing wasn’t "my thing" after years of feeling underwhelmed, I would’ve missed out on one of the most fulfilling parts of my life. The same goes for love and relationships—you don’t always fall head-over-heels on the first date, and the "perfect" person might not reveal themselves immediately. Give yourself permission to explore before deciding what’s right for you, whether it’s a person, a career, or a new hobby. -
Let go of perfection—it’s anchoring you down.
I spent years trying to match my father’s effortless competence at sea. Spoiler alert: That was never going to happen. His experience is his own, just like mine is mine. We often enter new relationships (or revisit old ones) with this belief that we have to do everything right—that we have to be flawless—when the truth is, letting your imperfections show creates authenticity. Just like on the water, it’s okay to occasionally bob around before finding your groove. -
Trust others to take the wheel.
One of the scariest things I did that day was hand over control to a six-year-old. (Okay, not full control—I’m not a lunatic.) But I learned that trusting someone else, even in small ways, can be liberating. The same holds true in life: You don’t have to do everything alone, and you certainly don’t have to steer the ship all the time. Sharing responsibility and vulnerability builds stronger bonds, period. -
Celebrate the small victories.
When we docked, Theo and his friends erupted in applause. Was it because I’d successfully taught them to sail? No. They were clapping because we didn’t hit the buoy they’d all been convinced was out to destroy us. Their joy was so contagious that I couldn’t stop smiling the rest of the day. Life is brimming with small victories if you give yourself room to see them. Learning to laugh at the little wins—like tying a slightly ragged bowline—is sometimes the best way to savor the bigger ones when they arrive.
Beyond the Buoys: Finding Similar Joy on Land
After that summer, I found myself seeking joy in other pockets of my life. I stopped overanalyzing the "how" and started embracing the "why." The why, as it turned out, was less about results and more about connection—both with others and with whatever task or endeavor I was part of.
Take relationships, for instance. I used to obsess over the dynamics: Who was initiating plans? Was that playful teasing or a subtle critique? Did their text mean "I’m into you" or "Thanks for the free appetizers last night"? But once I adopted the same spontaneity I found at sea—living in and enjoying the moment—the joy of connection became undeniable.
Now, whether I’m hosting a casual dinner party or falling into that easy rhythm with someone on a foggy coastal trail, I remind myself that joy doesn’t come from controlling the current. It comes from tuning in to where the wind is carrying me.
We’re All Navigating—And That’s Enough
It’s funny how one random day doing something I didn’t think I cared about forever changed the way I approach not just hobbies, but everything. Joy, as I learned, isn’t flashy or planned. It sneaks up on you when your guard is down, when you stop clutching the tiller so tightly and look at the horizon instead.
So if you’re reading this while feeling stuck—stuck in a job, stuck in a relationship, stuck in life—here’s what I know for sure: Joy isn’t something you find by forcing it. Say yes to things that might surprise you. Trust yourself enough to let someone else steer—even if just for a minute. Laugh when the boat rocks more than you expected. And, most importantly, take comfort in knowing you don’t need to have it all figured out.
The sea may be unpredictable, but the wind hasn’t failed me yet.
