Self-Awareness on the Open Seas (Well… the Choptank River)

Self-Awareness on the Open Seas (Well… the Choptank River)

I recently had the opportunity, nay the privilege, this summer to sail aboard a nearly century-old vessel called The Flying Cloud. The Cloud is a Chesapeake Bay log canoe that was built in 1932, and one of only 22 left in the wild that carry on a tradition of log canoe racing native to the Eastern Shore of Maryland (it even has its own Wikipedia page).

But this post isn’t about the boat – err, canoe – it’s about the experience, it’s about sailing and self-awareness, how it brought about that feeling of wonderment and a sense of being a kid again.

It’s not just a recreational activity. Sailing is a profound journey that offers more than wind, water, and waves. Sailing teaches us valuable lessons about ourselves.


I like to think that I’ve been gifted with a good sense of self-starting at a very young age, but nobody’s perfect. And it’s times like the one I’m recalling today that remind me of that. Luckily for me I can confidently say that I am ahead of the curve when it comes to self-awareness, thanks to my profession and experience working with the Predictive Index. In particular, having taken a PI Behavioral Assessment. If you haven’t yet completed one, I highly recommend it because you will fast forward YEARS ahead in terms of self-awareness and self-development.

Anyhow, I got a call one afternoon a few weeks ago from a buddy of mine, “Hey, are you up for some sailing this weekend? We need a few guys to round out the crew.” And true to my style, being somewhat low in Formality and not needing any more details other than that, I said “Sure! When do we set sail?” He hadn’t even gotten to the free beer and lunch… This is something that has played out all through life and career. The natural proclivity to just go with the flow, try new things, and meet new people. It’s something deep down I knew about myself already, but reflecting on the first time I took a PI Behavioral Assessment, it was something that could be objectively measured, something I could put on paper. It is a part of me that at times has led me on great adventures and great fun, but also if unchecked can get me into some trouble. THAT was the part I hadn’t quite grasped prior to taking my assessment. And in this situation, saying “Yep, where do I sign” could have landed me in a jellyfish-laden Choptank River if I wasn’t careful. It wasn’t until I showed up at the docks of the Cambridge Yacht Club that I learned about the notorious instability of these log canoes and the frequency in which they capsized. But, I wasn’t thinking about that… I let my low Formality and my high Extraversion drive my decision – get out there and try new things, meet new people! What’s the worst that could happen?



Knowing your strengths and weaknesses, embracing adaptability


One of the first lessons sailing imparts on you is the importance of recognizing your strengths and weaknesses. Fortunately, I have PI, but many don’t. Lean into my low Formality, lean into my low Dominance. I am a sponge – teach me. I also saw my high Extraversion kick into top gear, an attribute that helps me connect quickly with others and motivates me to not let my fellow sailors down. I wanted to be liked and I wanted to make a connection with these guys so they would invite me back, so I had to be on my game. We get out there and they tell me I’m going to be a “boardman”, one of the sailors that throws a 16-foot plank over the side of the canoe and hops onto it to balance the ship. WHAT?! The good news is that what sounded somewhat terrifying turned out to be pretty fun (and great exercise).



Becoming self-aware is a journey – much like sailing – that can help you become a better leader and person (not just a better sailor). Through self-awareness we can better gauge our emotional and behavioral responses to adversity and learn to adapt. Just as a skilled sailor trims the sails to catch the wind, self-aware individuals adapt their behavior to make the most of every situation.

To elevate your own self-awareness, get out on the Choptank and race a log canoe… OR, if you only have 7 minutes to spare, take a PI Behavioral Assessment. You’ll be glad you did.


Client Success Manager

Clayton Ramsey

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