Don’t Tell Me I Can’t Sail Away (Literally) in Midlife

By Helen Iatrou
April 03, 2023

Don’t Tell Me I Can’t is a series designed to celebrate all the ways you can forge your own path well in midlife and beyond.

I was 46 when I decided to finally pursue my dream of learning to sail.

I’ve lived by the sea, in Australia and then Greece, my entire life and always loved anything involving the water. As a youngster, I was devastated when my father sold our family’s little motorboat.

For years, I had put off the idea of acquiring a sailing license, as I was somewhat obsessed with building my career and assumed I didn’t have the time for such “frivolities.” Physics was never my strong suit. At school, I was incurably shy and never actively pursued joining a sports team, except for softball. So, I had no idea what to expect from my two-month sailing course. Would I fail abysmally and make a fool of myself?

But I quickly learned that sailing is deeply fascinating in that it’s both an art and science. Nothing I’d ever experienced could compare with the intoxicating freedom I felt when skimming across the water in a sailboat. This was love, and from that moment, I knew my life would change completely.

My First Yacht Race

To my surprise, I gained my permit, and about a couple of weeks later, my friend Klea, who owns a sailboat with her husband and has been sailing for some 26 years, asked me if I wanted to join her in a day race that weekend. I jumped at the chance.

It was a warm spring day, and the sun was beating down on the gleaming white, meticulously maintained 56-foot performance cruising yacht as I surveyed the largest winches—drum-shaped mechanical devices used to trim (adjust) the sails—that I had ever seen. Slipping on my sailing gloves, nervous excitement made my skin tingle. Klea introduced me to the crew, and soon enough, we were out on the bay limbering up at the start line.

I was assigned sail trimming duty, which is what I enjoy most. However, I was slightly disappointed that this boat had electric-powered winches. This meant I would mostly be trimming the jib, the front sail, with the press of a button rather than manually winding the winch. Why take all the fun and physicality out of it?

Fortunately, wind god Aeolus understood I was a newbie and delivered a light, steady breeze for most of the race. But as we made the tension-filled approach toward the finish line, the wind suddenly started to howl. Laser-focused on the task at hand, I was preparing to release the rope (sheet) attached to the jib as we tacked (turned the boat toward the wind) so my fellow trimmer could haul in the sail on the other side.

Amid the pressure to overtake our competitors, I released the sheet, but somehow it coiled around my wrist in a flash, like a cobra. As the wind pushed into the jib, the sheet trapped my hand, and I froze in fear, knowing the sheer force could snap my slender wrist. Standing beside me, seasoned sailor Klea promptly shouted above the wind to inform the captain and crew, and deftly freed my hand.

Well and Truly Hooked on Competitive Sailing

I was impressed with how calm I was. Fortunately, I escaped with a bruised wrist. “This is a big boat, and big boats mean greater physical forces,” Klea explained afterward. My battle scar disappeared, but I was well and truly hooked.

From that day, I signed up to every day race, weekend race, and weeklong regatta I could. I was working in tourism marketing, but it wasn’t making me happy. I was experiencing frequent mood swings and mild depression, and I wanted out.

I yearned to return to my first professional love—journalism. I wanted to be my own boss so I could travel freely for work and leisure and, above all, sail as often as possible. Growing demands from my superiors also made things feel impossible. Little did I know it at the time, but I had entered perimenopause, though I didn’t immediately recognize the symptoms.

There was nothing I looked forward to more than twice-weekly race training sessions, when I could literally feel the knots in my foggy brain come undone. Among other things, sailing forces you to focus on the present rather than stress about the future.

Embarking on a New Life

Sixteen months after boarding a sailboat for my first lesson, I left my job. I thought, “Hey, if I can leap fearlessly around a fast-moving vessel as it tilts (heels) at a 45-degree angle, feel deeply energized when powerful winds roar through the sails, and am able to handle huge swells without feeling seasick, why not dive headfirst into it creating my own business?”

A couple of years later, just seven months before my 50th birthday, I accepted my greatest sailing challenge yet when I joined the crew of my club fleet’s pride and joy: its fastest performance racing yacht.

Named Erytos 2 after the fastest Argonaut to pursue the legendary Golden Fleece in Greek mythology, this sleek 44-foot boat glides across the sea, its massive sails turning heads at every start line. It’s neither the latest model racing yacht out there, nor does it always win, but the adrenaline rush of riding this wild bronco of the water is indescribable. Thrusting a first-place trophy in the air is the icing on the cake.

Similar to the oft-unpredictable conditions of the sea, racing performance yachts involves facing unexpected obstacles every day. As a 50-year-old woman in the male-dominated world of yacht racing, I need to work at least three times as hard. Mistakes I make are not forgiven. I’ll occasionally hear a snide comment from a fellow crew member.

Discovering Me Through Sailing

Sure-footed and wiser, the 50-year-old me stands in her power. I know my worth and the value I bring to the team. I stay true to my positive nature and marvel at how far I’ve come in a short time.

As in my first race, I stay rigidly focused. Because I know that sailing, like life, is a constant, challenging learning curve. And no matter what, I plan to stay on board for a long while yet.

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