Decision Time

So now we come to the crux move. It’s decision time. And as those of you who know me can attest, I torture myself over personal decisions. I get there, eventually, but it’s never easy. Here’s where I’m at right now:

Further in the boat lift headed back to the water after being treated and released by the boat docs

Further is back in the water after a few days on the hard having the shaft seal and two through-hulls replaced. So I am mobile once again. And the Salty Dawg Rally, for which I am already registered and paid, is scheduled to depart Hampton, Virginia (at the lower end of Chesapeake Bay), tomorrow morning, and there’s no way I can get from Annapolis to Hampton by then (it’s about a 20-hour trip on the boat) and I’d want to spend a day or two in that area resupplying before heading offshore, so that’s out, right?

Well, the weather router who does forecasts for the rally said conditions over the weekend did not bode well for a Saturday departure and instead advocated leaving Monday afternoon. That’s doable for Further and I. And even if it isn’t, we could still head out to sea later in the week or next weekend or even later in the month.

But here’s the thing: I’m nervous. Scared, even. Yeah, I said it. I’m scared.

No, I’m not scared about the boat sinking or dying or hurricanes or anything like that. Further is a sound, ocean-crossing vessel, and the weather can be forecast (to a point, but to a point where severe stuff can be dodged over the course of a weeklong trip).

I’m nervous about all the things that can go wrong that are way less than sinking but still significant. Things that are significant financially, to be blunt.

The canvas dodger, which protects the cabin, is disintegrating after many years in the sun. I haven’t been able to get the rig (the mast and the shrouds that hold it up) checked. The jib has some tears in its edge. The engine runs fine but it’s old. The newly replaced shaft seal still leaks—but it will for a little while until the flange seals with use. And I wonder about just how much it will cost to live down in the Caribbean.

Every single one of those fears has a rational counter. I don’t need a dodger, and I now own a heavy-duty sewing machine so I can patch the holes (once I learn how to use the damned machine). The rig is and has been solid, as far as I can tell. I have some sail tape (and the aforementioned sewing machine) with which I could fix the jib (not that I know how). The engine, as I said, runs fine. The flange on the shaft seal will seal soon. And the guy who redid Further’s electrical system, a local boat-whisperer who knows EVERYTHING about boats and cruising, remarked the other day that living in the islands is, “on the cheap.” Hell, I even have a willing—nay, gung-ho—crew rarin’ to go.

So why the fear? The answer: I don’t know. I’ve always been one to jump at chances. Case in point: I got offered the job in Alaska on a Thursday; I was on the road on Monday and in Anchorage on Wednesday. That’s impetuous. And I didn’t just visit Montana, I moved there.

So again: why the fear? Is it age? Could be. A lot of people ask me how I can afford to do such a trip and the answer is: if I were a typical modern American, I can’t. I’ve spent a significant chunk of my retirement on chasing this boat dream. And I haven’t worked in two-and-a-half years. Having some money coming in rather than just going out would be a really nice change.

To that end, there is one job opportunity here in Annapolis that is intriguing. (The interesting job in D.C. about which I wrote earlier evaporated; my friend and former coworker found what he called “a slam-dunk candidate” who got the gig.) But there is a yacht brokerage agency is looking to pay someone for some office/marketing help—someone to help with their website and social media and such—while also training that person to become a broker. I have no interest in being a used-car salesman, but such a situation might be a way for me to break into the marine industry. This agency believes I might be that person and wants to talk later today, and I am inclined to listen.

Along another line: earlier this week I sent out an invoice for some freelance copywriting I did for another former coworker of mine. That felt good: doing the work and then issuing an invoice. It was just a few hundred dollars but still, it’s a start. Or it could be. Do I stay here in “society” and try to establish a freelance career? If I could get that going, that would be something I could do from anywhere—say, on a boat in the Caribbean. Do I stay in the States (if they still exist after Tuesday’s election) and address the issues/concerns I have about Further while also building up my cruising kitty and establishing an income source for the future, all while living in a place I like and where I have a lot of friends, and then go next year? It’s a compelling argument.

And then there’s this fabulous quote from late actor Sterling Hayden. The guy was a movie star, but before that he grew up in a rough-and-tumble orphan’s existence in Massachusetts and Maine, and he became a Grand Banks fisherman and then a sea captain. As a captain, he even ran guns for what was then the CIA into what was then Yugoslavia during World War II. In short, the guy was a badass. But he has this fabulous quote to which I return again and again:

To be truly challenging, a voyage, like a life, must rest on a firm foundation of financial unrest. Otherwise, you are doomed to a routine traverse, the kind known to yachtsmen who play with their boats at sea…”cruising” it is called. Voyaging belongs to seamen, and to the wanderers of the world who cannot, or will not, fit in. If you are contemplating a voyage and you have the means, abandon the venture until your fortunes change. Only then will you know what the sea is all about.

Granted, that’s easy to say when you’re a movie star and can fly back to Hollywood to make a cool hundred grand in a month (exorbitant wages in those days) whenever you’re broke, but the sentiment remains. (And the continuation of that quote, the first one on this page, is equally brilliant.)

But all the signs I get from the universe tell me to go. I even changed my phone’s lock screen from a photo of the late, great Spoondog to an exhortation that reads, “Life will only change when you become more committed to your dreams than you are to your comfort zone.”

And that’s what it all comes down to: stay in my comfort zone or chase my dream. In years past, I’d have already leapt. And I started my leap with this dream. But for some reason I’ve paused at the end of the diving board. Whether I take the plunge or tiptoe back to the pool deck will be determined in the next few hours. Stay tuned.