She Found Freedom—and Joy—in Learning to Fail

Photo credit: Monica Garwood
Photo credit: Monica Garwood

If only rebooting your mindset was as easy as restarting your laptop. As part of a collection on shifting perspectives, writers share the struggles, revelations, and joys they experienced as they began to see themselves and the world around them from a different point of view—and experts weigh in with advice on how you can change your perspective on just about anything.


The first time I went surfing on my own, outside the cozy bubble of a lesson, I ignored the break a half-block from my house, opting to wrestle a brand-new board into my car and drive to a different beach. With all nine and a half feet of it stretching across the passenger seat from the dashboard through to the back, blocking my sightlines, I was an accident waiting to happen. But at least all my new neighbors wouldn’t see me flailing and falling and failing in the water.

I’d never been much of an athlete. As a middle-aged novice, I felt like an anti-natural surfer: slow, inflexible, weak. Yet the first time I tried it, on a whim in Montauk, New York, those miraculous few seconds when I managed to stand and ride a wave brought me such immense joy that I was hooked.

It was clear that developing even a basic proficiency would require intensive practice. But the biggest challenge surprised me: I would have to give myself over to something I wasn’t good at and might never be.

I’d grown up in an achievement-oriented household; in elementary school, my mother told me, “When you put your name on something, it means you’ve done the best you can.” And for my father, who could be volatile, judgmental, and mean when he’d been drinking (which was often), nothing short of perfection would do. Depression-era strivers from Harlem, they instilled in me a sense that excellence, respectability, and money were the keys to unlocking a happy life unfettered by racial discrimination. Failure—especially when everyone can see you—was anathema. I abandoned anything in which I felt I couldn’t excel: piano lessons, a painting class, a magazine job.

I found surfing, or it found me, at a time when I was trying to be different in the world: braver—less hung up on how things were supposed to be, more focused on how they felt. For years, I’d had a nagging sense of dissatisfaction despite my ostensible achievements—successful journalism career, handsome husband, Brooklyn townhouse. I suspected I’d let a more adventurous me recede in my pursuit of an urban bourgeois idyll involving homegrown produce, backyard dinners, and local wine bars. Even as my husband and I drifted apart, I clung to the marriage, the townhouse, and a steady income, unable to imagine a different kind of life or how I’d bear the scarlet F of failure that would accompany their losses.

Surfing forced me out of that. Getting heaved off the board again and again—and loving it—compelled me to see that I’d been boxed in by fear of looking like a fool. After my husband and I divorced, I began taking the subway to the Rockaways on weekends for lessons. I was still a mess in the water, but I kept at it, because the alternative—robbing myself of the joy of surfing—would be far worse. I was exposed to a different approach to life by the oceanside, one that put the pursuit of happiness at its center, rather than trying to squeeze a little joy in between obligations. Eventually, I sold the townhouse and moved to a tiny bungalow in Rockaway Beach so that I could surf almost every day.

After that ridiculous drive, I began surfing near my house—it’s why I’d moved there, after all. There are still days when I have to talk myself into giving it a go. But I’ve learned to focus on the experience rather than strive for a particular result. On bad days, I latch on to what I can do to improve, rather than dwell on what I can’t. Or I just have a good time, appreciate the aquatic wilderness: the way the light falls on the water, how the cormorants dive for fish and the dolphins play in the waves.

And on good days, I realize how liberating failure can be. It means I’m willing to chase joy, to have faith in myself, to persist, no matter what anybody else might think. That’s what success now means to me—the willingness to chase what you love and find happiness in that pursuit. As the oft-quoted axiom goes, “The best surfer out there is the one who’s having the most fun.” Some days, no matter how bad I look, I swear that’s me.

—Diane Cardwell is the author of the memoir Rockaway: Surfing Headlong into a New Life.


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