Updated: Apr 1, 2020
There would be many people today who would feel content to live the life of a pirate. Freedom to sail about the beautiful Caribbean, guided only by the need for water and the lustful pleasures of plunder, these men and women lived a life that was free to be nudged in whatever direction the trade winds prevailed.
Disney’s Pirates of the Caribbean captured my fascination with such a life when I was a younger kid. Captain Jack Sparrow was a witty and prideful man who seemed to be caught up in the struggle to perform selfish pursuits for success and valiant acts of bravery to save the world. Through it all, he has a trusty compass that doesn’t point north. To the well-trained sailor, Jack’s compass (both moral and navigational) and demeanor seem misguided and unorthodox.
What these sailors do not realize is that Jack’s unique compass points to something far more worth knowing than North. Jack’s compass points to the thing that its beholder wants most in this world. Against what others see as “the right think to do,” Jack goes about life in a manner that is all his own, saving the world and learning things about himself he thought he already knew. The compass in Jack’s possession represents an idea about understanding what is right and wrong for each of us and is a device I so often wish I had the opportunity to hold.
As I sit at the foot of the Caribbean this week and gaze out over the ocean, millions of things shimmer on my mind, like the stars I see strewn across the sky that lays over the water. With so much to do and so much life ahead, I often think about what it would be like to live a life where I manned the helm of a vessel and crew that could take me wherever I wanted to go. Where would my compass point?
I am an expatriated Yankee who has found life in the south to be very content. The warmer weather and proximity to the beach do well to curb my anxiety. As such, I am quite sure that my compass, like Jack’s, would not point north. Instead of a location, I think about this idea more in terms of the type of life I want to live; a life completely guided by my own pursuits and ambitions and one where I am in control, not of the outcomes but of the direction of travel.
A pirate’s life draws a great comparison to the canvas that I wish to paint the portrait of my life upon. A life defined by tropical waters, untraversed island destinations and unexplainable escapades of danger and conquest sounds like one worth writing about to me. Some people are born, breath, and die and take 80 good years to do it without ever having crossed enough ocean to tell a worthwhile story to a stranger at Captain Tony’s Saloon. That’s not going to be me.
Being in Key West for a week has done well to exercise my liver, reset the amount of patience that I have, and inspire me to think more about what’s out there and care less for careless people. I admire those who throw away convention and live a life unbridled by the whisperings of others who have no pride in themselves. Key West seems to be a place that has plenty of the latter type of people. They subscribe to a way of life embodied by Hemingway and guided by Jack Sparrow’s compass to a life that is completely their own. I want that for myself. I want that for all whom I call friend.
Out of it all, I think we all need to appreciate those who have a compass that doesn’t point north. It takes the tenacity and courage of a pirate to create a life for oneself that is completely comprised of their own making. Captaining the helm of their own ship through the hurricanes of life is by no means an easy task. There are certainly tempting ports of call along the way that promise safe harboring and fresh water but a dangerous life of predictability for those who stay. Filling the barrels with water and rum to last you through the next adventure is long enough a stay for me. In the end, there may be a place that entices me enough to plant my flag and settle the land but I haven’t found that island yet.
For now I spend my days searching for a vessel and a crew to captain and take on a life of unrestrained freedom. My sincere wish for any who read this is that you too look inside yourself to discover your compass. Where does it point and what can you do today to begin your journey in that direction? Do not spend precious time squabbling with the drunkards of the port-side tavern. Rise above the mentality of the masses, find a boat and set sail aboard the deck of Destiny. She will guide you to islands that no other map could ever take you with treasures any man would desire. I’ll see you out there on water under a blue sky and black flag with a compass that doesn’t point north.
While finding myself in Key West, I have taken to some of these songs!