Should I Stay or Should I Go?

Sunrise from Further at the dock

Annapolis, Maryland, is a neat little city. Its downtown core — home to the U.S. Naval Academy, the state capitol and the city’s waterfront — reminds me a lot of Newburyport, Mass. Both cities share a rich maritime history, both are laid out in red brick and both have great ice cream stores (well, Newburyport used to).

The only difference is that Annapolis is much bigger. That, and the ocean is a two-plus-hour drive from here (many, many hours by boat), unlike Newburyport which is right on the Atlantic. If Naptown (as it’s known) was on the ocean, I’d have moved here a while ago. Why? Well, Annapolis is also the yachting capital of the country. Newport, R.I., sometimes makes that claim due to having hosted the America’s Cup for so many decades, but there is so much more sailing-focused business and activity here in Annapolis that Newport might as well be in a field in Kansas.

The same view that evening

Annapolis is also where my boat, Further, and I are currently located. And it’s my location that is the major quandary perplexing my brain these days.

I purchased Further in mid-November, too late to take her back to New England since all the marinas had already pulled in their docks and packed every square inch of land with boats on stands for the winter. That didn’t bother me too much since it’s just an 7.5-hour drive between Naptown and Plum Island and I could get back and forth relatively easily (although I will say that I am WAY over that drive at this point). I figured I could leave the boat in the water, head back and forth often, and work on the boat AND get my sea legs back. Or I could live aboard in Naptown and maybe get a part-time job locally through the winter. Either way, I’d spend the winter getting my and Further’s acts back together before next spring when we’ll head back to New England.

My view upon waking up

There’s another possibility that is tugging at me a bit, however: I’m thinking I could take the boat down the Intracoastal Waterway to someplace warmer — Florida, perhaps — for the winter. It’s been nippy enough waking up aboard Further the last few mornings that America’s third-world country down south seems quite appealing.

But I’m in an area of Annapolis that is really appealing. Eastport, known as the Maritime Republic of Eastport, is the funky section of town, home to great pubs and restaurants, a lot of boating businesses and a funky crew of locals that have a vivid joie de vivre. And I’m currently living in the funkiest part of Eastport — Stella’s Stern and Keel Marina — which I’m really enjoying. My neighbors have returned following Thanksgiving and they’re all really nice, really interesting people. It’s been great settling into the neighborhood.

Twilight in June’s Cove

That funkiness does come with a price, however. Up here in June’s Cove, the water is thin. When we get a big storm that blows all the water out of Chesapeake Bay (as happened the first weekend I was at Stella’s), Further’s keel sits on the muddy bottom at low tide. It’s not damaging the boat but it does make me wary and it means Further can’t get in or out until the water rises again.

And then there’s the aforementioned distance to the ocean and the chilly nights. Maryland DOES get winter so I’m expecting true cold and even some snow later in the season. It’s still only November.

So I’m really in a fix right now as I wrestle with the possibilities. I will definitely head north next spring, but what to do for the next four to six months? How much sailing/motoring would I really do here over the winter? What if conditions are good but the water level has me stuck at the dock? But am I ready enough to even consider heading down the ICW for Florida at this point? And if I’m not in New England for the winter, what will I do about hockey? (Yes, as trivial as it may sound to you, hockey is a big part of my life so it IS a factor.)

I blame this poster…

Among the things that tipped me over the edge into buying Further was the image I use as my laptop’s wallpaper. It reads: “Life will only change when you become more committed to your dreams than you are to your comfort zone.” Hockey and Plum Island are right in the wheelhouse of my comfort zone, so maybe stepping away from both of them is a good idea, an impetus for growth. To be honest, the hockey this fall has been great but I’ve been stagnating at the island, with nothing really going on other than helping my brother with projects around the house. Even if I’m not doing much down here in Naptown or any farther south, at least I’m making progress with Further and pushing that dream along. So it seems as though prioritizing a life that enables me to work on the boat is the way to go. From there, as detailed above, the questions arise.

Well…stay tuned, I guess.

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Take To The Ship

Say hello to Further

The eyeglasses weren’t the only long-impending event to recently — finally — occur. To paraphrase Andy Samberg (caution: VERY explicit language): I own a mother@#$$#@ boat!

That’s right: After 35-plus years of dreaming, scheming, reading and gaining some small bit of experience, I finally grew enough of a pair to drop some serious coin and buy a sailboat. And my first reaction was, naturally: HO. LEE. $#*T!

The boat dream goes way back to my youth. I learned to sail at summer camp and then my family had a Hobie Cat I sailed off the beach at Plum Island during the summer. Too many surfing magazine stories about tropical idylls and too many Jimmy Buffett songs cemented the image in my head of a wind-borne escape to warm, turquoise waters with perfect waves and no crowds.

And I came close a couple of times to approaching the dream. When I came home after playing hockey in Europe, I had a little bit of money saved up and I found a 1950-something Hinckley yawl in South Carolina for sale in magazine (the World Wide Web had yet to be invented). I asked my mother for the ten grand to make up the difference and, knowing full well my dream, she immediately said no. Can’t say as I blame her but boy, what might have been…

Looking aft from the bow during the sea trial in early November

In the fall of 2011, after an amazing summer of crewing for my friends Boogie and Marlies in the WAY North Atlantic (there are tons of posts on that time contained herein; see the archives in the right-hand column), I began surfing boat listings online. Boat porn, as it’s called, became a serious addiction, but it almost paid off right away when I found not just one of the boats I’d dreamed of since I was 13, I found THE boat: the exact one I’d seen in photos and stories was available. I made an offer that was accepted, but upon doing a survey (an inspection), I learned that there were issues with the hydraulic centerboard. I pulled my offer and the yacht broker turned into a serious dick, yelling about how it was no big deal. Several months later, I was once again aboard a boat with Boogie and Marlies, this time in St. Maarten for the Heineken Regatta. As it turned out, we were in a slip in a marina next to the guy who had been the project manager on the aforementioned dream boat when that Rhode Island company had been going full-bore in the 1970s and ‘80s. I told him what the survey had revealed and he exploded (in classic Yankee style) that what the broker had suggested as a fix was “goddamned stupid” and that the broker “didn’t know what in the hell he was fucking saying.” So I felt like I’d dodged a bullet, but I was still kinda bummed.

I took this selfie while at the helm during the pre-purchase sea trial

I came close on a couple of boats in the summer of 2012 but never pulled the trigger. And when all the shit went down in October of that year — Mom’s sudden passing and Dad falling and breaking his hip — I wound up relieved that I didn’t have the additional burden of a boat. But I kept surfing the boat porn just in case.

And then this summer, there it was. A Dutch-built boat (hey…Boogie and Marlies are Dutch! It’s a sign!) was listed in Annapolis. It was a bit out of my price range but I kept my eye on it now and again because that brand of boat had a reputation as strong, solid, fast boats, and that’s what I wanted. But I couldn’t quite rationalize the expense the owner was asking.

Three weeks before the Annapolis Boat Show, which I would once again attend and help a friend of mine whose company has a booth at the show, the price dropped by almost 25 percent. I called the selling broker and saw the boat the day I arrived in Annapolis. It was nice and it was in good shape. And it was calling to me.

I called an Annapolis broker I’d worked with in 2012 and asked him to represent me — I didn’t want to go into such a deal without an advocate on my side of the table. A few offers and counters, a survey and a trial, and I closed on the boat two days ago on Friday, Nov. 17, 2017. And again I say: HO. LEE. $#*T!

The view forward

The boat is a Trintella 42. It is 42’3” long and is a sloop rig. It has two cabins — so that you married friends can come visit me and you’ll have your own, private cabin — as well as two heads (toilets, for those unfamiliar with the nomenclature), a nice galley (kitchen) and saloon (living room).

She is currently called Glory but I’m going to change her name to Further. Why? Well, further is where I want to go. And Further was the name of the bus Ken Kesey and the Merry Pranksters drove around for the acid tests in the ‘60s. The bus was their means for searching for higher truths and I’m hoping my Further will be the same for me — without the need for pharmaceutical assistance.

I moved Further yesterday to her new home at a funky marina way up at the head of a creek in Annapolis (my broker said of the owner of the place, “he’s a funkmeister.”) The place has a dozen or so slips, most occupied by folks who live aboard, and there’s a small bathroom/shower in a shed on shore. Wedged in at the head of the creek as we are, there are a lot of ducks and herons and trees and quiet. What there isn’t is glitz or glamour. I like it. I also like the cheap rates and walking access to Annapolis/Eastport lifestyle.

The current game plan is either: a) leave the boat here in Annapolis for the winter and either live aboard or make frequent trips down from Plum Island to work on the boat and get my boating legs back (I needed my broker’s help to move the boat yesterday; who am I kidding…he did the move I just helped); or b) get the boat ready to go ASAP and head down the Intracoastal Waterway to Florida and spend the winter getting my legs back there. This Thanksgiving week will be the time I make up my mind on that front.

Expect to see a lot of the posts hereabouts to involve this major step in my life. And it is just that: a major step. It’s not just a new toy. I’ve had two great dreams in my life: one, to live in Alaska; and two, to sail away. I accomplished the first. Now it’s time to (finally) go for the second. In fact, this second dream took root in my soul a few years before the first. And who knows? After my time in 2011 aboard a sailboat in places like northern Norway, Iceland and Greenland, it may just be that Further is my ticket to combine my two dreams. You may just see me sailing away to Alaska one day…

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It’s a Young Man’s Game…Or Is It?

A bunch of different threads in this post today, the result of a bunch of different threads “runnin’ around the ol’ Duder’s head”  the past few weeks. So bear with me while I talk through things out loud. Hey, it’s cheaper than therapy, although a lot less effective, I’ll grant you (and probably not very interesting to you).

So, a month ago I wrote about how I’d thought about spending the summer when I was 26 at the surf break known as the Mexican Pipeline. I finally made it there this year, in March, when I turned 51, and I wasn’t ashamed to say that, upon my arrival, the waves were intimidating.

Puerto Escondido definitely intrigues me as a potential long-term destination. (I have every expectation that if I wind up dying of old age it will be in a foreign country. After seeing the way my father, a World War II veteran, was mistreated by this country’s health system, what can a selfish deadbeat like me expect as his body starts to wind down? But that’s a topic for a separate post.) But when I thought about spending significant time in a surf-focused life, I wondered if that really made any sense to an aging (as are we all) middle-aged man.

Puerto Escondido is a destination for young surfers from all over the world, and there’s a reason that particular demographic overruns the town during peak season. It takes strength and fitness just to step into the ring at a serious wave. And while I still go to the gym and play hockey and lead a generally fitness-focused lifestyle, well, there’s a reason I play in the over-50 hockey tournaments now. Can I still handle a wave like Puerto? Yes. But it’s exhausting. And potentially dangerous. And my recharge capabilities aren’t what they once were. Those are just facts.

So when I look at potential paths I might take — and I do that a lot as this year in which the generations of my family changed hands winds down — I question whether such a pursuit is an appropriate core focus of my life. In fact, I question WHAT should be the focus of my life to come.

And that’s an important question because in just a few months my father will have been gone for a year, at which point (or shortly thereafter) my role as executor, trustee and caretaker of the family’s assets and physical legacy will come to a close. And I have some decisions to make.

Do my brother and I keep our family’s house (our sister has no interest in keeping her share)? Does that mean I remain living there? If so, what do I do for a living around here? If not, do we rent out the house? Or do we sell? If we rent or sell, where should I go and what should I do? And if we keep the house, how do my brother and I come to terms about what we should do about various aspects of the house’s management and upkeep (and who should pay for them)?

Questions of career, location, home, legacy — questions that have built up over the close-to-a-hundred years of my parents’ lives and the lives of the children they produced, including me — are about to require an answer. And as those of you who know me well can attest, I have a wide range of interests and dreams pulling me in an even wider range of directions.

The security of a “straight” job back in Corporate America has its appeals but in my field those options are largely out west. And even if they’re in around here, among the reasons I didn’t opt for a commuting-into-Boston career when I got out of college is the fact it’s a hellacious, dangerous, expensive and exhausting commute from Plum Island. And it still is. But shouldn’t I be maximizing my income (and savings) at this point in my life in an attempt to set up my so-called “golden years”?

Or: What about carving out some sort of niche, working-for-myself career? Can I parlay my skills (cough, cough) and experience into something that lets me work from, say, the office on the third floor of the house at Plum Island? Travel — to Boston, New York and beyond — is easy enough. My mother always implored me to be my own boss (as she was), but I’ve yet to make that happen. Maybe I can create enough of a career yet stay at home — and keep that home in the family. But can I even create that career now, at this age?

Speaking of which: underlying all of these internal (now external) debates is the aforementioned fact that I recently turned 51. I’ve already experienced light doses of ageism and I can only expect them to increase, right? Is Corporate America or building one’s own career every bit a young man’s game as living for surf in a grubby apartment in Mexico?

Then there’s the age-old dream — and those of you who’ve known me for any length of time have heard me talk about this since I was a teenager — of buying a sailboat and taking off. I came close back in the ‘90s (Mom, in her infinite wisdom, refused to help me out financially then, for which I remain thankful). I came close in 2011 (which, given what happened to Mom and Dad in 2012 and 2013, I’m glad fell through). And when I returned to New England last spring I planned on two things: one, helping Dad; and two, buying a crappy, old boat and fixing it up to head south in November. That plan went with Dad in July, but there’s no reason the plan can’t be resurrected this year.

I follow the journals of friends who are living a life of early retirement. I follow those who continue to work but live on the road. I monitor the experiences of those courageous souls who never bought into the system in the first place. Hell, I even adore the fictional character Travis McGee and his plan for “taking retirement in installments.” So the pull of that dream I’ve had since I was a boy remains strong. And this might be the time to make it happen. Selling the house would certainly generate enough cash to go. Keeping the house and renting it out would generate at least some income on which to live. Hell, there might even still be enough money left in my savings to go as I’d planned to last year (though I’ve been burning through a lot of it this year as I’ve been living at the island and chipping away at what’s needed doing), but would managing that be more trouble than it’s worth?

No matter what I wind up doing, I still need some sort of purpose in life though, don’t I? Elon Musk raised the question of a universal basic income as a response to the rise in workplace automation, but questioned what, if anything, such “free” income could do for people in terms of a reason to live. As I’ve been mostly idle for the past year, I’ve come to realize that a focus, a calling, a purpose is a good thing. It’s a requirement, actually. Elon’s right.

Which brings me back around to today’s original question: What to do when those things that might function as a focus in my life are largely geared toward those (much) younger than me? Do I rage against the dying of the light? Or take up a serious golf habit?

These are the things I ponder of late. A lot.

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