Learning to Surf at 50

On Fear, Growth, and the Things We're Finally Ready to Try

A solid start surfing with a little help from my friends

“Have you ever surfed before?”

The question hung in the warm evening air of Yoga Studio 2 at the Hotel Tropico Latino in Santa Teresa, Costa Rica. Our surf instructor Davide — Italian-born, Costa Rican at heart, and patient in the way that only great teachers are — scanned the semicircle of women gathered on the creaking wooden planks of Yoga Studio 2. This was Ground School: our first lesson, and one that would take place well outside the ocean.

I paused to remember. And then I found it.

“Yes.”

I was almost killed by an outrigger canoe the first day I learned to surf at 24 years old.

—-------------------

My surfing story begins 100 yards off shore in Waikiki, Oahu. I’m alone in a crowded lineup. The sky was a brilliant blue and the ocean copied the color perfectly. I was underwater for only seconds, presumably after falling off my board trying to catch a wave. I emerged gasping for air just as the next wave crested overhead. Directly before me, streaking toward me at full speed, was a six-man outrigger canoe paddling hard to catch the same wave. I was suddenly, totally in their path. Without time to think, I took a deep breath and spastically dunked below the surface, surfacing again just in time to watch the orange canoe glide away.

Those handful of seconds are all I can find when I search my memory for that first day of surfing. I had put the experience on a shelf in my mind, letting it sit unshared — like so many of my experiences from that year lived alone on Oahu.

I was 24, working my first job out of college in public relations on the 8th floor of the Pan Am building on Kapiolani Boulevard. Every day I peered down from my office window to watch surfers pedaling their cruisers toward the ocean, surfboards tucked under their arms. I yearned to switch places with them — to be outside, schedule-free, moving toward something instead of away from it. Instead, I spun my chair back around to my desk and counted the hours until I could walk home in the soft evening light.

What I found after months on my own, far from everyone I loved, was a dull emptiness I didn’t know what to do with. I was an outsider — a haole — an enthusiastic foreigner who had arrived to further dilute a culture already fractured by centuries of outside intrusion. I was young and insecure of my place in the world, feelings amplified by the history I carried in my head of how these islands had been forcibly taken. I took an intellectual approach to belonging, reading the definitive history of Hawaii from my balcony on Ena Street, soaking my feet in warm saltwater and olive oil, reasoning that if I could just understand what makes Hawaii Hawaii, I could find my way in. I never quite did.

That bashfulness — about being haole, about being young and unskilled and over my head in more ways than one — followed me into the water the day I tried to surf. I had no business being so far off shore alone. I had no skills to fall back on, no instructor beside me, no one watching. When the outrigger canoe nearly took my head off, what I felt wasn’t just fear. It was confirmation of what I already suspected: I didn’t belong out there.

I didn’t surf again for 26 years.

—-------------------

The evening we arrived at the Pura Vida Adventures Surf & Yoga Retreat, I kicked off my flip flops and stepped into Davide’s classroom with equal parts excitement and trepidation. I was here to celebrate turning 50 with friends, keen to get reacquainted with a sport that had unfinished business with me. What I did not share with the group — in case it added to anyone’s fear — was the outrigger canoe. I kept my nerves on a need-to-know basis. I was ready to look forward, and had little room for fear to get in the way of the growth I was after.

Looking around the semicircle, I was curious about what had brought each woman here. Joy was determined to overcome a fear of having her head submerged in open water — a lingering fear from learning to swim late in life. Cherith dreaded being taken out by a wave and hurting herself. I was afraid of hitting someone, or being hit — the outrigger canoe never entirely left me.

But my deeper question wasn’t about safety. It was about capability. I knew I was strong. I train hard, I move well, and I have spent years building a body I trust. What I didn’t know was whether the particular kind of strength surfing demands — the explosive paddle, the pop-up, the sustained balance on an unstable surface — was strength I actually had, or strength I would have to find. Those are different things. I was less afraid of failing than I was curious whether my fitness would translate, whether my body would meet this specific challenge the way I needed it to. That question didn’t scare me. It lit me up. When I felt the edge of apprehension creeping in, I didn’t push it away — I got curious about it instead. Which, as it turned out, was exactly what Davide was about to teach us.

At 50, I’m much further down the road of not caring what people think of me. But sitting in that classroom, I recognized something familiar: a desire to excel — not to impress anyone else, but to confirm my own hopes that I am still ready and able to meet the physical challenges that unfold before me. That I am still someone who does hard things.

Davide pulled out a whiteboard and drew a Venn diagram — three overlapping circles labeled Mind, Ocean, and Science — converging in the center to create what he called the Stoke. The Mind circle was about growth mindset: no fixed destination, only forward progression, every mistake a movement toward mastery if you’re willing to learn from it. The Ocean was about reading your environment — finding the peak of the wave, understanding where to position yourself, watching which direction the break was opening before committing. Science were the skills and techniques that get you onto that wave — the paddling, the timing, the pop-up, the sweet spot, and the glide.

Then he offered us something I’ve been thinking about ever since. An acronym for transforming how we experience fear: DIPI.

Dangerous → Interesting → Pleasurable → Important

The model is simple: when something strikes us as dangerous, we can choose to look at it through the lens of curiosity instead of threat. By seeing it as interesting — even fascinating — we open ourselves to the possibility of finding it pleasurable. And when we find it pleasurable, we discover it was important all along. Important to our growth, to our sense of self, to our understanding of what we’re capable of when we dare to think bigger than our fear.

I have spent my career as a leadership coach teaching versions of this idea to other people. Growth lives on the other side of what scares us. The fear is a signal that we’ve left the comfort zone and entered new territory — where we can try, fail, and try again. Standing barefoot in that yoga studio, I felt the particular humility of receiving wisdom you’ve spent years giving away.

—-------------------

The first morning in the water, I walked in carrying my blue longboard, feeling fear as a mild resistance — a familiar tightening in my chest — and then I kept walking. I let the ocean envelop me and decided to give it everything I had. My confidence grew each day. By day three, a handful of us were deemed ready to paddle outside the break to catch green waves.

Fear poked me in the side again. The old fears came roaring back — surfers bearing down on me, a wave swallowing me whole, my board spitting out one way and me the other. The morning I was first to paddle outside, I dressed the part: a new floral long-sleeve surf suit, green-leaf surf leggings, what I called my jungle pants. If I was going to meet this moment, I was going to meet it fully. I pressed past my known limits daily, turning the dial up a little further each time, driven as much by curiosity as determination — genuinely wanting to know what I’d find I was capable of.

It turned out I could catch those green waves pretty handily. My sense of balance was steadier than I expected. Once I found my sweet spot — the center point of balance on the board — I could ride the wave until the momentum died out. Staying on the board was harder than popping up, it turned out. But I kept going.

—-------------------

By the last day, I turned the board toward the wave break and caught two long, solid rides on smooth, hollow green waves. I stood on my sweet spot — knees soft, shoulders relaxed, head high — and let the wave carry me all the way in.

I didn’t think about the outrigger canoe. I didn’t think about the 24-year-old alone in Waikiki, too scared and too green to know what she was doing out there. I didn’t think about the 26 years I’d spent keeping this particular door closed.

I just rode the wave. And when it finally gave out beneath me, I threw my arms open, hollered into that wide Costa Rican sky, and felt something I can only describe as all of me — body, mind, and whatever else I’m made of — arriving in the same place at the same time.

That’s what lives on the other side of Dangerous.

Not just pleasure. Not just pride. But the specific, irreplaceable feeling of discovering that you are still capable of surprising yourself — that at 50, the door isn’t closing. It’s wide open.

I came to Costa Rica to learn to surf. What I remembered is that I am someone who does hard things — not because they’re easy, but because of everything waiting for me on the other side.

These are my now years. And I intend to spend every single one of them finding out what else I’ve been afraid to try.

—-------------------

If this resonates, subscribe! Share it with a woman in your life who is ready to take more risks and reap the rewards — with a lot less noise and a lot more joy. The Now Years publishes every week. Don't keep it to yourself.