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The Other F-Word - What I’ve Learned About Failure and Sailing

Writer: Dianne MacGillivray
Dianne MacGillivray
Aug 10
3 min read

Failure. The other F-word.


What comes to mind when you hear it?  For me, it used to be disappointment.  Shame.  That sinking feeling in my stomach when I tried something and it didn't work.

I used to hide my failures.  Avoid them.  Tell myself stories about why I shouldn't try again.

Then, I bought a boat, and failure became my most consistent teacher.


What Failure Looked Like Before

I spent years on the sidelines, wishing I had the courage to try new things, but too afraid of looking foolish or even worse, failing.  I'd see people doing what I wanted to do and I'd just stand there, watching and wishing it was me.

I was afraid to fail.  Afraid to try again.  Afraid to even start.

My mindset was: "Why bother?  I'm going to fail anyway."

So, I spent more time worrying about failure than actually focusing on the task at hand.


Great blue heron and cormorants hanging out on a large fallen tree in the St. John River.
I'm the Great Blue Heron, watching from the sidelines, but I didn't stay there forever.


What Failure Looks Like Now

Then I bought a 40-year-old sailboat, and failure showed up, a lot.

  • The first time I tried to hoist the main halyard and it was curled like a 1980s perm.

  • The time I cut the main wire to my power system because I was tired and not paying attention. (Yes, on purpose.  No, I don't fully remember why.)

  • The mooring I missed in front of the entire yacht club.  (I could hear the laughter from the deck.)

  • The kayak that floated away while I was sure I'd tied it off.  (It was right there and then, it wasn't.)

 

But here's the thing: I survived all of it.  I laughed.  I learned.  I tried again.


What I'm Learning About Failure

I used to think failure meant I wasn't good enough.  That a real sailor wouldn't make those mistakes.

Now I know: failure is just feedback.  It's not a verdict.  It's not a final answer.

It's just the boat telling me: "Try that differently."


A Sailor's Take on Failure

Think about sailing.  You're never sailing in a straight line.  You tack.  You adjust.  You correct course by a few degrees, over and over again.

That's not failure.  That's how you get where you're going.

I've learned that success, in sailing and in life, isn't about avoiding mistakes.  It's about making small adjustments and keeping going.

Sailboat facing a series of channel markers.
Tiny Adjustments. Right?

What If We Changed the Story?

What if we saw failure as:

  • A predictable part of learning

  • Not a sign of weakness

  • A chance to try again

  • Just feedback

  • One step away from success

 

What if we were curious about failure instead of afraid?


Where I Am Now

I don't view failure quite the same way as I used to.  I'm not as afraid of it.  When something goes wrong on the boat and rest assured it will, I’ll try to learn from it, laugh about it and try again.

Sometimes I still want to hide.  Sometimes I still feel that old shame creeping in.

But now I also know: failure isn't the end.  It's just a course correction.


Closing Reflection

Failure isn't the opposite of success. It's part of the journey and if you're sailing, literally or metaphorically, you're going to encounter it.  The question isn't whether you'll fail.  It's whether you'll let it stop you and that's a lesson I'm still learning. One sail at a time.

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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. You can too.

 

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