The Invitation That Changed Everything
- Dianne MacGillivray

- Feb 5
- 3 min read
How a week with a woman sailor rekindled a dream I thought I'd drowned.
It all began with a song. The harmonies of CSNY’s “Southern Cross” and “Lee Shore” planted seeds. A dream of freedom, adventure of quiet sails, beautiful sunsets/sunrises. It was a romantic dream and we chased it: 2 CANSAIL courses, a tippy International 420 we aptly named “The Get Wet Boat,” and the big step up to a Pearson 30, we had the dream in the palm of our hands. The only thing missing at the time, was retirement.
But on that Pearson, something broke. I can’t explain it. It was like a switch that flipped. One moment I was fine; the next, as my husband hoisted the mainsail, I was sitting in the cockpit, head between my knees, a white-knuckled, hyperventilating mess. The dream was happening, and I was its saboteur. The fear was irrational and I knew it, but it persisted and followed me to our next boat. A MacGregor 26 M, our ultimate dream boat, so we thought. My anxiety continued and I completely lost any self confidence that I had left. I had given up on the retirement dream of sailing into the sunset.
Meanwhile, my sister-in-law had a different story. She was learning to sail and loving it, with her friend, Duffy. Her invitations were a steady, gentle drip on my resistance.
“Go, you’ll love it.”
“She’s a great teacher.”
“You won’t be scared.”
For two years, I said no. My internal monologue was a shroud of dread: “Impossible.” “What if I panic?” “What if I need to walk home from the middle of the river?” I still really wanted that dream to come true and felt horrible that it wouldn’t happen because of me.
Then, finally, I said yes. The instant the word left my mouth, the pit in my stomach opened wide. What have I done?
I arrived at the beach, braced for the old familiar terror. But what I found was a completely different world.

Duffy’s boat wasn't just a vessel; it was a sanctuary. There were no assumptions, no unspoken tests of skill. There was patience, clear language and laughter, so much laughter. The pressure to perform for a partner, the fear/anxiety, the ghost of past failures began to evaporate in the simple, competent camaraderie of a woman on the water.
When it came time to hoist the sail, my heart still hammered. But this time, I wasn't alone with my fear. I was beside someone who understood it without judgment, who guided me on the tiller and who celebrated the simple act of trying. The mainsail rose and I stayed upright. I breathed. I even smiled. She yelled, “Nailed it!”


That week didn’t just teach me to sail again; it taught me why I had stopped. It wasn’t the wind or the waves. It was a lost sense of agency, a narrative of fear and anxiety that ran on repeat like a broken record. My experience with Duffy changed my life in ways I can’t begin to explain.
It was the spark that led me, just a few years later, to own my own sailboat. It’s the reason I write this blog, for anyone who has ever felt that their dream is sailing away without them, who hears “you won’t be scared” and thinks, “but you don’t understand.”
I understand. And the first, bravest step is sometimes as simple as saying yes to the right invitation.
Has there been a “Duffy” in your life, a person or an experience that unexpectedly re-routed your journey? Or are you waiting for the courage to say yes to an invitation that scares you? I’d love to hear about it in the comments.


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