“How about it? Fancy a surf?” The Australian man stood in front of a rustic beach shack, the sun glinting off his perfectly tanned muscles and long blonde hair.

Despite the pretty sight, I knew exactly how to answer that question: with a quick shake of the head followed by a tale of how I saw Jaws when I was five years old and the fear it generated in my young, fragile psyche caused me not only to avoid oceans for the next decade but also to quiver in the face of pools, bathtubs, and, on occasion, toilets. By the time I was 20, I usually explained to anyone who was still listening, I could finally swim in a lake without a panic attack but it was a few more years before I’d go in the ocean. It wasn’t necessarily sharks I was scared of: it was the dark, murky unknown and the fact that enemies I couldn’t see or communicate with could come and attack me. As a control freak who’s always sort of expecting the worst, I can deal with an ambush; I just want to be able to see it coming.

Roughly two years ago, I decided it was time to get over a number of things—mostly myself, and the stories I believed about what I am and am not capable of. Helen Gurley Brown hadn’t let anything limit her—not the fact that she was from Ozark, Alabama, didn’t know a soul in the advertising and publishing worlds, and was the lone woman working in a sea of men. I realized I had to stop allowing myself to be governed by a childhood fear. So when I went to the Dominican Republic in 2009, I signed up for a windsurfing lesson.

The instruction began with a handsome British surfer taking out a dry erase board and drawing arrows and stick figures on it before going into a long and complicated lecture on upwind and downwind. I could tell that what he was saying was at about a third-grade level but dry erase board lessons, not to mention conversations about the wind, don’t tend to bring out my most focused self. My mind had been wholly adrift when I suddenly heard him ask, “So which way is downwind then?” I took a 50-50 shot and guessed wrong. He moved our lesson to the beach and began showing me different foot positions and telling me what various parts of the board were called.

But out there on the water, I stood right up. Of course, I also fell right off but after my third rise and fall, something the instructor had said in front of the dry erase board came back to me. A wave has two sides, he’d told me. Don’t panic when the first one hits—just breathe and it will pass. It worked: I never fell again. It was only then that I realized how much I needed to follow that direction in my day-to-day life.

If I ever needed evidence that living the Helen way changed me, it came in my answer the other day to the Adonis-like Aussie. “Sure,” I said before I had time to think about upwind lectures, about whether or not I’d be able to stand up, or about sharks. He and I went tandem surfing—me on the front of the board, him on the back—catching our first wave and every wave after. The next day, he took me out paddle surfing, where I stood up and rowed my way around the cove on my own board. But then the day after that—yesterday—he was busy. No problem. I coaxed a new friend into swimming with me out to a buoy. The water, my former enemy, had officially become my friend.

She and I were calmly swimming through the turquoise, glassy water when she suddenly yelped and told me she’d been stung by a jellyfish. As she explained the sensation—“like a hair has fallen off your head and is wrapping itself around your body”—my first thought was fear that it was going to happen to me. My next was that it wouldn’t—that whenever you think something’s going to happen, it doesn’t. The one after that was that I was suddenly experiencing just what she’d described except that it was about 100 times more painful than her description: I could swear a sharp electric rope that had just been struck by lightening was lassoing itself around both my legs.

It had finally happened: the dark, threatening presence in the water got me.

We made our way back to shore and discovered that I had welts all over the front of both of my legs—and the back of my right leg, which didn’t actually hurt—while her skin had no marks. I had gotten it and gotten it bad. The Aussie surf instructor put vinegar on my battle wounds, explaining that it was Portuguese man o ray that had nabbed me. People gathered around. One offered antihistamines to help with the swelling, all offered sympathy.

The thing about pain is, of course, that it subsides. Within an hour, the stinging had stopped and by the time I headed back from the beach, the bubbling welts were just tiny bumps.

Pre-Helen, I might have considered my jellyfish bite confirmation that my fears are legitimate and let that keep from going back in the water. But when your mentor is a woman who stayed single for decades after everyone else she knew had married and continues to work at Cosmo today, at the age of 89, that’s just not going to fly. Besides, it’s undeniably empowering to experience something you’d always feared and discover that it’s not even close to as horrible as the anticipation of it was. Which is why I went swimming today and am planning one last surf before I leave tomorrow.

If I encounter a shark, though, all bets are off.