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Why I Sail And Write About It

  • Writer: Dianne MacGillivray
    Dianne MacGillivray
  • Sep 26, 2025
  • 3 min read

Updated: Jan 4

For the Scared Souls

Let’s get real: years on the water didn’t stop me from being a white knuckled, hyperventilating “sailor” when the mainsail went up, head between my knees, utterly convinced that I’d never not be afraid on a sailboat. But here’s the unexpected twist: I now own a sailboat, with its share of fumbles.  Like the time I thought I was in neutral and wasn’t, then hit the concrete wharf like I was a real pro.  All eyes were on me when the contact crunch sounded in the air and the chatter on the wharf went silent for a moment.  Or watching my kayak ghost drift past several rafts of boats.  I was sure I secured it.  Yes, the cameras came out.  I’m sure there’s a video somewhere out there of this, especially entertaining event. 

 

Courage isn’t the absence of fear—it’s the art of sailing through it. And if a woman who once cried over a hoisted mainsail can now laugh while untangling halyards, trust me:  Your ‘I can’t’ might just be a stubborn knot waiting to be undone.

 

For the Nature Lovers / Soul Searchers

The beauty and mystique of the river’s natural world and wonders seem endless.  From the quiet, misty mornings, the solitude of amazing sunrises and sunsets, to wild waves and winds.  The quietness and stars at night make me feel blessed to be a part of all of this.  Spotting birds, seals, fish jumping, beavers, otters, deer and other river dwellers is always thrilling.  The river gives life, respite for the soul searcher, the burnt out, the lost and maybe even the lonely.

 

For women reinventing themselves

Finding courage, confidence, camaraderie and themselves, it's all here on the river, where it whispers, “Come as you are.”  The river doesn’t care about your resume, body shape, wrinkles or your hairy legs.  It only asks, “Will you try?” That’s what I did.  I went from giving up on dreams, feeling small in the world, too scared to try things that I really want to do and afraid of getting it wrong. Being severely depressed at different times in my life, I thought, “Is this it?  Is this how my life is going to play out?”  Sailing has been a life game changer and I will be forever grateful for the river, sailing and to the special people who said, “Yes, you can!”

 

Just to be clear, I’m not a seasoned sailor.  I’m an ordinary woman trying to live an extraordinary life.  I’m retired and bought my boat in the fall of 2023 and I sail as often as I can.  Yes, sometimes I use duct tape, sometimes my kayak flips and the camera goes in the drink (true stories).  It’s not perfect, but it’s an incredible adventure.  This journey isn’t about perfection.  It’s about showing up for yourself and others. This is why I sail and write about it.

 

If any of this speaks to you, then I wish you the warmest welcome.  Join me and let's see what kind of mischief we can get into. 

 

Tell me about one of your fumbles. I’d love to hear your stories.

 

“Sometimes the smallest steps in the right direction end up being the biggest step of your life. Tip toe if you must, but take that step.”  

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Meet The Skipper

The day I bought my sailboat Gypsy Wind

Hello, I'm Dianne MacGillivray.  I'm a novice sailor finally facing down fear, depression, and chronic pain; one sail at a time.  I bought a boat named Gypsy Wind to trade in my "hyperventilating lump of mush" era for one filled with freedom, duct tape, and showing up for myself (and others) along the way.

 

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