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Sailing and Other New Tricks


I’ve been sailing many times. No, that’s not true: I’ve been sailed — passive voice — many times. I suspect I’m the kind of person for whom the term “deck fluff” was coined. I can tell you all about the iguanas and gas powered blenders on tiny islands in the Bahamas. I can’t tell you much about lines or cleats.

But all of that is about to change. Now that I have moved to a lakeside town, I have decided to learn how to sail with my fiancé. Our first class was last week.

I thought we’d start out by learning sailing terminology on terra firma and perhaps graduate to getting into a dinghy in week two or three. Nope. The first thing we learned was how to reverse a 25-foot sailboat, take it out in the harbor, spin it, and then take it back to the marina and park it in a teeny tiny slip.

As I took the tiller to park, I thought I’d have all of the success of Cinderella’s ugly stepsister, trying to jam her great big foot into that little wisp of a shoe, but I managed to park the boat just fine. Old dog, meet new trick!

Then we tried our hand at knot tying. It took me 40 years to figure out how to tie a scarf around my neck in a way that makes me look remotely French, and yet in a twenty minute lesson I learned how to tie four types of knots.

I remember in early adulthood how painful it was to learn a new sport–I’m looking at you, golf–but now, in later adulthood, it’s so much easier. Perhaps I’m smarter… doubt it, or more relaxed… not a chance. Likely, I simply care less what other people think, which frees me to make mistakes and learn. Also, I’m more ready to push the limits than I’ve been in the past. I’m at the age where friends are receiving scary diagnoses and people my age have died. It provides a good incentive to break through my fear of failure.

On our next lesson, we are going to race our boat. In a race. On race night. It sounds fun. Also, terrifying.

I’m mindful of my fiancé’s 97-year-old grandmother, who regularly posts photos on social media where she is riding on motorbikes and in powerboats with her white hair blowing wildly and a big smile on her face. I get it.

There comes a point where you realize life offers no guarantees anymore and you only have so much time to do what you need to do.

I’m finally throwing caution to the wind and raising the sails. Life is too short for me to be content as a passenger any longer.



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With an MBA in Finance, JEN LAWRENCE worked in investment banking; was Executive Director of a Children’s Museum and is a pioneer mommy blogger. Jen writes and speaks about women in business, critical thinking, strategic planning and is the author of Engage the Fox: A Business Fable About Thinking Critically and Motivating Your Team. When your world’s been blown apart, Jen Lawrence can help you pull yourself together, and pinpoint those next steps that will help you find your new normal. She can also be found at

15 thoughts on “Sailing and Other New Tricks”

  1. I love stories about midlife women leaping into new adventures and surprising themselves with what they are actually capable of. Good on you – and may the odds be ever in your favour on race day 🙂

  2. Insightful, inspiring and beautifully written! Thank you, Jen. And I’m now a little in love with your fiancé’s grandmother, by the way! Esther xx

    • Aww. Thanks, Esther. Grandma Rose is very loveable. She’s also dating. Which is all kinds of awesome. I want to grow up to be her one day!

  3. I have been sailing twice or been sailed and I think it’s like taking steps to heaven–blue sky and sea, sunlight (I was lucky) and the sounds of waves. Not to mention the movement, the rocking, I love it all. Thanks for the memories. Beth

  4. Jen,
    What a way to learn to sail. Pardon the pun, but it sounds like “sink or swim.” Right out of the box you learn how to reverse the boat in and out of the harbor and next, you’re going to race at night? Amazing! I want details!!!
    xoxox, Brenda

  5. I like that – “I have been sailed…” – I’m going to use that phrase… a lot…! I live with a boat person. There is always a pile of rope – excuse me – line – piled up in the house somewhere, and bags of foreign objects from West Marine scattered all over the place. I’ve crossed oceans happily as rail meat, but perhaps the time has come to take a more active role… You’ve inspired me to sign up for lessons…

    • Well done! I don’t think I will ever be sailing obsessed (my sailor friend gets boat cushions for her birthday: I’d never encourage that!) but I am enjoying a more active role on the water.

  6. Looks like it’s anchors aweigh for you! How exciting! I love your realization that your comfort was the simple result of not caring what other’s thought of your efforts.
    Thank you for the inspiration.

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