Adventures in Sailing: A Metaphor for Life

You need wind in your sail and the boat will move forward.

When was the last time you took up an unfamiliar sport or hobby?

As adults, we tend to stick with what we are good at.

It’s fun to learn something new as long as we don’t have to make a fool of ourselves.

Or risk failure.

I can’t draw a straight line. I have two left feet. I flunked gym. I’m bad with technology. I’m afraid of heights. I can’t carry a tune. I’m not creative.

My quest to say “Yes” in 2022 includes trying things outside my comfort level and experience.

I’ve had years of ballet training, so trying new forms of dance, while at first challenging, is still fun and familiar. Chance of failure pretty low. Fear factor-zero.

I knew I needed to stretch myself if I was to conquer fears.

It was time to raise the bar.

This summer I signed up for sailing lessons.

Before you say, Oh, how fun!, please know it was not on my top list of activities. In fact, applying to be a civilian passenger on a spacecraft ranked higher. (I did apply but that is another story.)

Prior to signing up, the only sailboat I’d been on was a 70 ft. catamaran in Key West. Now that was fun.

I got to relax, enjoy a margarita and good company, while a master skipper took to the giant sails. With a calm sea, perfect weather, and a spectacular sunset…What’s not to like?

My summer sailing lessons were offered through a yacht club on our town lake. The legendary sailing coach, Bob G. has been sailing, racing, and teaching for 50 years!

At age 80, Bob still possesses incredible strength and stamina.  I watched in awe as he jumped in and out of the boats, helping the students rig their sails. 

These sail boats are not huge. You sit low and close to the water. There’s no motor. You can’t quickly change direction or speed. There’s a feeling of vulnerability, at least for me, being out in one.

View from the Dock

And I had no idea there was so much involved in the sport. 

Putting on the rudder. Bailing the water. Lowering the boom. Rigging the main sail and the gib sail. Securing the ropes.

And that’s all before you leave the dock!

Upon returning to the dock or mooring, you have to do everything again in reverse.

Then there is the sailing vocabulary to learn: tacking, gibing, luffing, beam reach, in irons, centerline, starboard, port, leeward, fairlead, and clew.

My sense of direction has never been great, so learning the essential Points of Sail proved challenging, as well.

My Homework

I can still do a double pirouette but cannot tie a proper knot for the life of me. Can you, dear reader, tie a quick Bowline knot?  


At home I practiced tying with the help of YouTube tutorials. By the next sailing class, though, I’d forgotten the procedure.

This sense of defeat made me sympathetic to what my adult ballet students must have felt when I demonstrated the sequence of a seemingly simple dance combination. Why couldn’t they get it? I’d thought at the time.

It didn’t take Captain Bob long to pick up on my anxiety.

Instead of letting me sail with my requested partner our first time out, Bob assigned me to his boat, along with Mary, another sailing novice.

Bob was patient but firm, giving clear directions and expecting us to follow suit.

Never mind the information overload. At least I felt safe in Bob’s boat. He could read the wind and water like I analyze a poem.

Next lesson, though, we were on our own. Bob would monitor us, and the other class members, from his motor boat.


There were moments of panic in the middle of the lake when I was doing everything wrong, my partner’s commands coming too fast for me to process.

At times, I feared the boat would capsize. (Did I mention I don’t like swimming in lakes?)

Upon seeing the distress signal, Bob did not heed my request to return to the dock.

Instead, he sent his teenage assistant over in a rowboat.

The agile boy climbed in our sailboat. “What’s troubling you?” he said, sounding more like a therapist-in-training.

The boy assured me that we wouldn’t capsize. Or crash into the oncoming boats.

Though he admitted it could feel that way.

“Just do this to balance the boat,” he demonstrated, sitting atop the side and leaning far backwards. 

Ah, sure. Thanks.

Next class, just before sunset, the lake remained still. I began to relax and enjoy the scenery from a new vantage point.

I felt as if I’d stepped into a Monet painting.

“San Giorgio Maggiore at Dusk “

Bob rowed over to my boat, his arm sweeping across the gorgeous sky.“See? This is what it’s all about!”

After each sail practice, Bob did a debriefing back on land, offering tips on wind currents, sailing maneuvers, and safety measures.

Once, after spending a half hour just rigging the boat, pushing away from the dock and setting sail, he called us back in because of a lightning threat. 

After we gathered on shore, Bob reminded us of the old adage:

You can’t control the weather, only the direction of your sails.


That metaphor fit my life perfectly. What a great lesson for us all.

Karla’s Korner

* * *

On the last day of class, Bob pronounced us graduated. “Summa cum laude!” 

I think he was being generous with me. I’m no way ready to skipper a sailboat. For now, I’ve advanced from passive passenger to cautious crew.

Captain Bob

Learning a new skill is good for our brain. Doing something we fear is good for our spirit.  

This summer, I accomplished both.

I’m still working on that Bowline knot.

Call me Evelyn.

Christine Lindstrom

Author: EvelynKrieger

I'm a people watcher and word crafter, author of fiction and essays. I also blog on living the creative life during hard times. When not writing, I work as a private educational consultant. Special interests: dance, the moon, astronauts, beaches, poetry, staying alive.

33 thoughts on “Adventures in Sailing: A Metaphor for Life”

  1. Wonderful article. Bravo for being brave and taking on something outside your comfort zone. All I remember from a couple of sailing lessons at summer camp is “keep your head down!”–maybe not the best life lesson. But from taking up other things that I don’t readily excel at (such as running), I’ve found that there’s a lot to be said for mediocrity. To be part of an endeavor from within rather than from above gives a much better sense of the group experience, and progress–such as it is–is harder-won and more gratifying.
    Coincidentally, I recently started reading Moby Dick. I was a great fan of seagoing novels growing up, yet this one intimidated me. Time to take it on! By the way, Mutiny on the Bounty is a longtime favorite of mine. You might enjoy it all the more for your sailing experience.

    Liked by 2 people

    1. So nice to hear from you, Joyce. So funny about “keep your head down!” I forgot to mention that one. I almost got hit a few times. Now I understand the idiom, “lowering the boom”! Your comment about mediocrity is interesting, especially for us over-achievers. This gets into the beginner’s mindset which I’ve also wanted to write about. Children are usually open to such experiences until their failures are pointed out. In school, we ask kids to excel at everything at once!
      Another score for my Moby Dick reference. Do you find your attention span has shrunk from years reading stuff on the internet? What’s next Ulysses? Thanks for the recommendation. Haven’t seen the movie, either.

      Liked by 1 person

      1. Yes. I’m trying to get back into sports which I haven’t done for a while. It’s a challenge but it it feels good after. Will you sail again? I remember getting seasick one time on a 14 hour crossing with a ferry. Most unpleasant feeling 😁


        1. Yes, I will sail again on a Day Sail boat, but with an experienced partner. No worries about seasickness on the lake, but a few years ago I went to Block Island on a Ferry during inclement weather. 1 hour of hell. I thought for sure the boat was going to go over. 10 foot waves, higher than the boat. People vomiting. I called my kids and told them wear my money was stashed.😅

          Liked by 2 people

  2. Wow, Evelyn, this is so inspiring. You are so right about staying with what we know as we get older. And I find reading the wind so difficult as well so I’ve always been a passive sailor when out with my brother who is avid.

    For me, I’m finding that my kids push me out of my comfort zone as they pick up new things. Like this weekend when I found myself horseback riding because my daughter wanted to go.

    I’m so grateful for this piece that helped me identify the need to keep growing. I love how brave you are!

    Liked by 1 person

    1. I’m glad I achieved my goal of inspiring! It’s great for you to set a model of adventure and adaptability for your kids. haven’t been horseback riding in ages. I should add that to the list, though, I’m always wary of potential injuries. I also used to ice skate regularly; haven’t done that for a while, either. My daughter really encouraged me to take the solo trip to Guatemala last spring (which I referenced in Taking Risks in Life post). During those 8 days I did several things way outside my comfort level. Then there is also the idea of simply not liking to do things that don’t come easy or that we are only mediocre at, as my friend JMichel mentioned in her comment. For high-achievers that can be a tough call. Hope you have a great end to the summer season, Wynne. May your days pass happy wherever your ship sails.

      Liked by 3 people

  3. Your tales of taking some new risk remind me of my current use of Atlas Obscura to find inexpensive online mini classes for new ways to enjoy travel. Thanks for offering some sailing knowledge to your readers.

    Liked by 1 person

  4. Thank you for sharing your adventures and hope all the best as you follow your dreams!!.. Perhaps Mr. Twain were thinking of you when he made this comment; “Twenty years from now you will be more disappointed by the things you didn’t do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover, acquire new friends and gain knowledge of yourself and the world.” (Samual Clemens/Mark Twain)… 🙂

    Hope you find happiness at whatever port you put in to and until we meet again..

    May the sun shine all day long
    Everything go right, nothing go wrong
    May those you love bring love back to you
    May all the wishes you wish come true
    May peace be within you
    May your heart be strong
    May you find whatever you’re seeking
    Wherever you may roam
    And may happiness fill your heart
    each day your whole life through.
    (Irish Saying)

    Liked by 3 people

  5. Oh Evelyn, what an accomplishment! I love the idea of a quest to say “yes” to new opportunities, and I think I may try to adopt it. When we’re young, it seems there are chances to try something new at every turn. As adults, we have to go out of our way and break routines, but it’s typically worth it, even if all we get is a funny story.


  6. Love learning new things. After ten years at university going ever-deeper into philosophy research I jumped into things like sheep clipping (sheering), horticulture, cookery, and html coding. As you say, it does a person good to stay active in learning. Loved the description of your own experience too. Thanks 🙂


  7. Wonderful story of courage and adventure Evelyn! Pushing ourselves BEYOND our comfort zones—not recklessly, of course—is a very healthy activity for the soul and mind to become more and more whole as a human being. Bravo Lady! 👏🏻 Will you continue sailing?

    I’ve always been the Explorer/Adventurous type. I love, LOVE to learn new challenging, invigorating hobbies, tasks, etc. My (now ex-) brother-in-law was a competitive sailor with White Rock (Lake) Sailing Club in Dallas, TX. He taught me lots of fun, incredible tips on sailing. But pffffft, I can’t tie the various sailing knots to save my life either! 😄 However, being super athletic all my life, then playing soccer/football all my life on all levels on 4 of the Earth’s 6 inhabitable continents, he and I picked up inline-hockey and some ice-hockey for a few years. OMG, freakin’ LOVED that too! GO STARS! 😉🏒😁

    Have an idea for your next adventure/hobby?


    1. Thanks so much for reading and sharing your own experience in adventure in sailing and athletics. I plan to continue sailing but it will take more guidance for me to get comfortable. I expect my next adventure will be some travel. (6 continents? Impressive.) I don’t have much room in my life for another hobby. Currently, I’m in the midst of revisions for my novel which an agent requested. The process is intense and requires immersing myself in a fictional world, moving the characters and scenes around to make a more cohesive (and commercial, as the agent said) book. In other words, I need to buckle down! I’m looking for a quiet getaway where I won’t be distracted. So while I may not be pushing out of my comfort zone right now, I’m definitely PUSHING myself. Take care, Professor!

      Liked by 1 person

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