Finally Aboard

It’s Wednesday, April 11, 2017, and for the first time, while working on the boat in a St. Augustine marina with a tinge of sunburn on my calves, I finally feel unemployed and as if I’m standing in on my new home. It’s an unfamiliar sensation, but a welcome one. Exciting. Both in enthusiastic anticipation of upcoming adventures and “what the hell did I get myself into” anxiety. Reminiscing back on the journey that led me here, it was a long time coming…

It’s May 2015, and Brandy, Dan, and I are sailing from Ft. Lauderdale to the Bahamas along with several other people for a week long vacation. The entire week Dan continuously makes statements like “When we’re living
on a boat we can do [insert amazing thing here],” and responds to my general complaints about having a job with “You won’t have to do that if you’re living on a boat.” He is, of course, referring to the plan he and Brandy have had for several years to sell everything they own, move onto a sailboat, and jaunt around the planet for a while. They’ve never directly asked me to join them in a straightforward manner, but Dan’s assumptive statements have made it clear I’m welcome. This is our sixth trip or so together including one to the French Polynesian and several to the British Virgin Islands, and I’ve come to expect these remarks over time.

I can’t pinpoint the exact moment during the vacation, but at some point a new neural connection materializes in my brain and a synapse fires. Suddenly, for the first time I’m doing real mental calculations about the feasibility of joining them on their expedition. Maybe one of Dan’s comments finally broke through. Perhaps it’s the crossing of the channel back to Florida with a looming feeling of dread as I succumb to the inevitability of a tired familiar life of work, bills, taxes, and more work. If I’m being completely honest, I can’t pinpoint it because it’s mostly subconscious. The idea of joining them is still a distant fantasy I’m all too comfortable entertaining in a daydream, but too scared to embrace as a real possibility. So I cram in the last bit of fun in Ft. Lauderdale and board the plane home.

But the synapses continue to fire.

During the following week of work I somehow find myself pondering my mortality and wondering what my last dying thoughts will be. Laying on my deathbed and looking back at the timeline of my life, I imagine referencing Facebook to revisit pictures of old memories. And there I find Dan and Brandy’s timeline. Our respective histories intertwine with pictures of those six sailing trips we took before they left to travel the world and I stayed my course on land. Then, I remember an article I read years ago about the most predominant regrets people took to their graves and while I can’t recall the specific sorrows, I did retain the lesson. Almost every regret consisted of things people wished they had done rather than those things they actually had done (with the exception of spending too much time at work). So here’s my dying self looking back at the pictures of Dan and Brandy on their epic journey and me wishing I had had the guts to go for it.

And that’s all I need. That’s the tipping point.

My thoughts begin to shift from constantly coming up with excuses not to go for it, to proactively finding reasons to do it. If you work for 10 more years you’ll get 50 weeks of vacation, but even if you only take a year off you’ll get more time off than that immediately. Tomorrow isn’t promised, much less the day after or year after…holding out and betting on a retirement is a riskier bet than seizing the opportunity to enjoy life now. You’re young enough, talented enough to get a job when you do decide to come back…if you decide to come back.

It was only May 31 when Brandy, Dan, and I sat down at On the Border and I decided to officially join them. In the span of less than two weeks I had gone from assuming I would continue working straight through to retirement, to deciding to sell everything I own and jump on a sailboat to bounce around the globe for a while. Apparently, I also transformed a beard into a goatee in the same time frame.

Thank you for giving me the opportunity to join you, Brandy and Dan! I look forward to the many adventures ahead.

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