Thursday, June 7, 2018


Who doesn’t look back every now and then, and strain for a glimpse of what might have been, had they chosen differently?

A couple of years ago when I first embarked on this endeavor, I was reminded of my age, and that I was not going to be any spring chicken in the industry. I was told of the massive financial resources required to follow it through to completion, and the struggles that would bring.  A few close friends tried to nudge me towards sticking with ‘the sailing thing’. I could have listened, perhaps.

Many times in the last two years, I have felt like I’ve been beating my head against a brick wall. So many days I have faced the feeling that I’m not cut out for this, that my ability to learn just wasn’t what it was when I was younger. Beyond the seemingly never-ending self-doubt lay the plain old logistics of everything.  I had weeks on end of feeling like I was pushing a boulder uphill in the mud; that I’d never get to a plateau, and would end up being crushed no matter how hard I tried.  There were so many signs, pleading with me to give up. I could have heeded them, perhaps.

Boat deliveries over the past year have sporadically provided the necessary income to keep me going, but the uncertainty of finding the next job, and nothing being for-sure until the lines are cast off, have made an already weather-dependent, instructor-availability-dependent, aircraft maintenance-dependent goal very difficult to adhere to, or complete on any sort of defined timeline.
Hiking in Nevis

It would have been easy to give up.  But, over the years and my travels, I’ve observed many around me; the patterns, the ruts, the complacency, the personal history that implored them to keep repeating their habits that have them continue living in a manner that makes them old before their time. They’d rather resign themselves to living a life of quiet desperation than run the risk of changing their situation, and the perceived security they hold, for the possibility of attaining what they truly desire. But certainty and stability is nothing more than an illusion, and it gives us an erroneous sense of comfort. No matter how secure you think your job may be, or your home, or your closest relationship, none of it is truly for certain, is it?

Something within us is lost when we settle for the status quo when we yearn for so much more. There are a thousand different ways we can learn to suppress it; with distractions, alcohol, hoarding, obsessive tidying and re-organizing, retail therapy, or any other mechanisms of avoidance. A part of ourselves gets bundled up and tucked away, almost forgotten until maybe one day something is awoken with us, and we are overwhelmed by the time we think we’ve wasted.  At that point, many decide that it’s simply too late, and will close their hearts and minds, to better cope with the cards they think they’ve been dealt. For those folks, it is just that. Too late.

Finished my Instrument Rating with Yankee Doodle (Cessna 152)
But while some cards may be dealt, others are chosen.

After my six-month gig in Antigua lasted only one week (the same standards of professionalism and morals and basic laws about harassment and inappropriate behavior in the workplace often don’t apply to the yachting industry), I decided to return to South Florida, with the intention of finishing my instrument rating and commercial pilot license.

Training was periodically hindered when the circus came to town (you know the kind that exhibit such marvels like, oh, let’s say, a hippoPOTamUS) and the airport where I did my last few flights was completely shut down during these times, due to its proximity to the circus tent.

I have had some really fantastic people come into my life recently, many of them fellow pilots, who have offered everything from emotional and logistical support, to sharing their knowledge in the cockpit (Rick, Nancy, Rainer, Riley, Justin, Kimberly, Beth). Or, in the case of Beth and Jib, whom I met while sailing Annie Laurie in the Bahamas, a roof over my head as I completed my instrument rating in March and April.  I couldn’t have come this far without all of you.

Being a moving target for years on end sometimes has me worried that I’ve traded love for ambition, and that I’ve sacrificed a life I could have shared with someone, and everything that entails. It’s been a long time since I’ve felt a sense of community, or that I belong anywhere or am needed by anyone.  If those are sacrifices I’ve somewhat inadvertently made through the sum of my actions thus far in life, in doing so I’ve at least managed to not compromise the lifestyle that I consider fundamental to feeling alive.  I’m not sure that any one person could replace that anyway.

Wherever my life goes in the coming months, I’m looking forward to maybe, just maybe, staying put in one place for a little while. I’d like to meet some new friends who might be in my life for more than just a few weeks at a time. Sleeping in the same bed (or bunk) for more than a few weeks at a time might be nice, too... along with having refrigeration and a little kitchen (or galley) where I can rediscover the pleasure of cooking.  I’d love to have a little space of my own again, where I can sit with my diary or book and a cup of earl grey tea, and have the simple pleasure of looking out the window (or porthole) at the falling rain, or perhaps across the table to see someone looking adoringly back at me. If my next home is indeed a boat, I’m going to ensure it is more prone to floating than the last one.

I have little other choice than to continue living like a vagabond for at least a little while longer. Looking back on the past 2 years, part of me finds it incredible that I’m not living under Brickell Bridge at the moment (though my tent and backseat of my car have seen some good use).  I often go back to the notion that has thus far never failed me in life; do what you love, forget about the money, and the Universe will conspire to help you achieve anything your heart desires.

So far, so good.

Having recently completed all my requirements for my commercial license, all that remains is that final check-ride. It’s now just finding and scheduling a plane, an examiner, and a day of decent weather.  The hardest part is finally over.

I will never have to look back and wonder what might have been, had I only kept striving for what my heart wanted most. I will never have to wonder if I'm sleepwalking into the rest of my life. Because very soon, I'll awake from a dream that I turned into reality by never, ever, giving up.