Fair Winds and Following Seas, Sailor

Jill, in green, and the crew of Pure Puur in Bermuda in May 2013.

Jill and I were the graveyard watch the first night out of St. Maarten bound for Bermuda in 2013. We were crewing for my two Dutch friends, Boogie and Marlies, aboard the 70-something-foot luxury yacht the two pro sailors were running for a couple of rich Euros. I had first crewed for Boogie and Marlies in May 2010, also leaving from St. Maarten, that time bound for Newport, Rhode Island. And I crewed for them all summer long in 2011 as we three ran charter trips in the far northern Atlantic: northern England, the Shetlands, northern Norway, Iceland, Greenland.

So to say I’d had some experience with how Boogie and Marlies liked their trips run would be an understatement. And I had connected Jill, whom I’d met on a crewing website, with Boogie and Marlies when they were looking for crew for this trip to Bermuda.

True to my form, I puked up dinner the first evening out of St. Maarten. Whenever I haven’t been to sea in a long time, the first evening’s dinner pretty much always comes up. By the time my next watch rolls around I’m back to full pique and good to go for the duration. But maybe that colored some of Jill’s opinion of Luke the sailor during that late-night stretch. After all, she was a big-time racer, having been flown all over the continent aboard a private jet as part of the crew for some big-shot boat owner from Chicago. Key West, San Diego, Annapolis, Newport…Jill had raced in all the big-time regattas and here she was stuck with some so-called sailor who couldn’t keep his dinner down?!

Maybe that’s why Jill looked at me with such disdain when I told her NOT to mess with the sail trim on that late-night watch. I knew from experience that making such a racket might gain us another half-knot or so, but it was definitely going to wake up the skipper. And he had just gone to sleep and did NOT want to be jolted from his slumber. He’d put me and Jill on this first graveyard watch precisely because he knew that I knew how he wanted things to go while he slept.

But Jill’s racer mentality was new to cruising, to delivering a yacht, and she couldn’t help but tinker. Thing is: on a 70-plus-foot luxury yacht, the winches are electric. And electric winches make noise. A lot of noise. A lot of low-pitch, rumbling noise that makes even a 70-plus-foot yacht shudder.

She’d only rumbled through a couple of turns on the winch before Boogie’s head was poking out of the companionway wanting to know what was wrong. Nothing was wrong, Jill told him, just trimming the sails to try to get a bit more speed. He looked at me — after all, I’m the one who’d arranged for her to be on this trip — and all I could do was smile and shrug. It’s a long way to Bermuda, Boogie told us. Let me sleep for a few hours, please. You can trim the sails during the daylight hours.

Boogie went back to sleep and I couldn’t help telling Jill that I’d told her so. I did so with a laugh. And she took it with a laugh. And we had a great trip to Bermuda.

And that was how I connected with Jill. It was the beginning of a mutual ball-busting friendship that was filled with a lot of laughs and a lot of exasperated sighs whenever I’d chastise her about tweaking the sails for another half-knot.

When we got to Bermuda, Jill and Marlies went out and did girlie things. Shoe-shopping, I think. And together the entire crew enjoyed some of the sights of the island. As the other crew members filtered back to their homes in the real world, Jill and I took time to explore the nooks and crannies of Hamilton, Bermuda, and also several of the world-famous beaches on the island. She indulged my marathon walk to the Mid-Ocean Club, a golf course that had been the namesake of a prep-school friend who’d grown up on Bermuda’s Strat-O-Matic Baseball team back in the early 1980s (my team, the Honolulu Tubes, won the inaugural season). We must have taken half a dozen different buses and walked a good 10 or 12 miles in the course of our wanderings, but we saw corners of Bermuda that probably not a lot of tourists see. And we had a blast.

Jill came to visit me in San Diego in 2014, after I had reentered the work force and moved back to Southern California. We had a nice weekend and the next time I saw her was in July 2015 when I was in Chicago for the Grateful Dead’s final three shows at Soldier Field. Jill bicycled to the downtown area to say hi to my friends and I, and then she was off to play tennis, a passion of hers.

That was when I first saw that she was fighting the cancer. Before it had just been an abstract concept she’d explained to me in emails and on Facebook. But there in Chicago, as she wheeled up on her bicycle, she had an American flag dewrag on her head and looked thin, gaunt. Like someone dealing with chemo. But she also looked fierce, like someone you did NOT want to mess with. This chick was tough. It was clear cancer didn’t know what it was getting into when it decided to pick on Jill.

As part of her battle, Jill went to Boston on a regular basis as part of a medical trial at the Dana Farber Cancer Institute. She was also part of a trial at, I believe, Northwestern in Chicago. She was NOT going gently into that good night, and the next time I saw her, in Newburyport where she came up with her boyfriend from Salem to have lunch, she seemed as fit as a fiddle. That must have been in 2016 or 2017. And in 2018, after I’d bought a sailboat of my own in Annapolis, Maryland, I asked Jill if she wanted to help me take the boat back to New England. She said she definitely wanted to go, we just had to coordinate the trip with her schedule in the trials.

The crew of Further after arriving in Newburyport, Mass., from Annapolis, Md. (from right): Jill, Captain Ed and yours truly.

Which we did, and Jill, along with another friend, Captain Ed, helped me bring Further back to Massachusetts in July 2018. It was a fun trip, filled with a bit too much motoring, a bunch of really fun sailing, some scary weather off the coast of New Jersey, and good times in Block Island and Newburyport. While chugging along offshore she explained the various trials, which in the way she described them just seemed to me like her new normal and something she’d deal with for a long time to come. She was also vociferous in her disdain for the hypocrites at organizations like Susan G. Komen who were more interested in fundraisers than in actually curing cancer.

After the three of us got to Plum Island, we took Further out for a daysail off Plum Island and gave her a proper sail, complete with hoisting the asymmetrical spinnaker and ripping along at a great clip. Jill was in her happy place trimming the chute, constantly making micro-adjustments to keep the sail in proper trim and Further rockin’ along at full speed. We had a blast and it ended up being one of the best sails of the season.

By all accounts, Jill was winning her fight. She looked fit and healthy, and we had a lot of laughs both at sea and at the house on Plum Island. Then she went back to Chicago and in the fall I returned to Annapolis with only Captain Ed’s help. And Jill and I went back to staying in touch via electronic means again.

It was in a text message in late winter this year that she said she’d entered hospice care. I didn’t know much but I knew that wasn’t good. Jill didn’t elaborate and we didn’t really talk very often after that. I sent her a happy birthday text in early June and got a reply that said only, “thanks.”

And then today I learned that she passed away on June 30. Marlies sent a text message to which I could only reply, “Oh shit.” I went to Jill’s Facebook page and there it was: a string of birthday wishes in early June and then nothing until a post a couple of weeks ago by a friend saying she’d passed a couple of weeks before that. And with that, another funk settled over my world.

I realize I’m like the old man raging at the clouds when I say that I am getting SO fucking tired of having friends die. So be it: fuck you, clouds. And fuck you, death. Jill was a good one, with a great soul and kind heart and a captivating sense of fun and humor. She was also tough and strong. She fought bravely but apparently it wasn’t enough. Does anyone have enough? If Jill didn’t, I kinda doubt it.

Fair winds and following seas, sailor.


So where IS my head at these days? Where HAS my life been recently?

As I posted yesterday, I’ve been working at a yacht brokerage here in Annapolis. I took the job in November and spent the winter struggling to get the firm’s website up to date. I’ve mostly succeeded, completing a project they’d started in spring of last year and then let languish. But still, dealing with nitpicking and not being able to get sign-off on simple, must-have items is frustrating, to say the least. The combination of an inability to make a decision (or constant changing of minds) on our part and piss-poor communication and marginal skills on the part of the developer the firm had hired way back when made for a painful process through the winter and spring. And I’m kinda over the frustration that has lingered on into the summer, especially since it’s all been 1099 work so there’s no steady pay let alone benefits.

And I already covered the fun ’n’ games I’ve enjoyed as I’ve tried to sell boats in yesterday’s post.

Through it all, I’ve been doing the job-search boogie. I’ve sent resumes out on jobs that seemed like fits in locations ranging from Seattle to Florida, San Diego to Maine. And let me tell you: it has been humbling.

For starters, with all due modesty I can only assume I’ve been subject to ageism. Several positions that were spot-on fits for my experience and expertise never even garnered so much as a “thanks, but no thanks” response. Other places did send that response, which perplexed me because, again, the jobs were something I already had experience doing, and there aren’t a lot of people who’ve done the job of digital director at a broadcast TV station. To combat the ageism thing, I reconfigured my resume with the help of an HR director friend in an attempt to sorta hide my age. But if anyone spends just a tiny amount of time doing the math, they can figure out that I’m at least 50. Well, all I can do is keep plugging away.

One position that seemed a particularly good fit was a marketing manager position doing all the digital media for the New York Yacht Club. Sure, I might have seemed too senior for the job in the hiring manager’s eye, but I explained how, at this point in my life, combining my avocation with my vocation would be ideal. And to be home in New England? Perfect! I even, with the help of a friend, tracked down the communications director for the club who, it turned out, is a fellow Dartmouth grad (a few years after me). I sent him a personal email, which he replied to very soon after saying that were still gathering candidates and to be patient. I’ve still never heard so much as an automated “thanks for applying” response let alone a “thanks, but no thanks” email. And the job is still posted on the NYYC site.

I have made it to the interview stage in a few instances. I did a phone interview with a nonprofit in Florida, and while the thought of living in South Florida generally makes me break out in hives, job was with a fishing- and ocean-centric organization so, again, it was a chance to apply my skills to something of personal interest to me. I did three phone interviews with folks including the org’s president and then…crickets. Not even a “thanks, but no thanks” email (are you sensing a theme here?). That position also remains posted.

I actually made it to an in-person interview with an online-commerce company. That it was located half an hour from my home on Plum Island made it very interesting to me, even if it wasn’t right in my wheelhouse. Could I have done it? Yes. And I believe I’d have done it well. They at least had the decency to inform me that I was no longer in the running. And I got to see some friends back home while I was up there.

Finally, I’ve made it to an in-person interview with a nonprofit in D.C., one that is personally interesting to me given its focus and its activities. I’ll actually be going for round two next week, so stay tuned.

So what does all this have to do with taking to the ship?

Well, one of the factors in my quest to sail away is, like everyone else, finances. I’ve been eating up my retirement fund chasing this dream and, to put it bluntly, I’ve pretty much exhausted that fund.

So there’s that desire-to-eat thing goin’ on. There’s also the desire to be DOING something again, contributing my abilities to something of value. I get fired up when I see a job that seeks to apply my experience set to a topic about which I’m passionate. They’re rare, but as I detailed above, they are out there.

But then I ran into that boat while paddling yesterday and it was clear that he had accomplished what I long to do, and he’d done it with nowhere near as good a boat as mine. No, he wasn’t doing it glamorously, but I have no interest in glamor either. So it’s doable. The question is: do I dare? I don’t have an answer to that question yet.

There’s one other, not-at-all-minor factor in all of this and i all of my life, and that’s the house at Plum Island. My brother has been living there for two years now, most of which I’ve spent down here in Annapolis. None of the work is getting done on the house and I don’t know what my brother’s plans are — mainly because when I ask him, he doesn’t know what his plans are. But we can’t live there together and neither can afford to buy the other out. So we’re in a bind.

The thought of selling the house, of losing the house and losing Plum Island, literally breaks my heart. But I don’t know what other options there are. To that end, I sent my brother a letter last week saying I believed it was time to think about selling the house. I haven’t heard a word back yet.

I’ll be heading north in a week or two (to have my car, still registered in Mass., inspected) and hopefully my brother and I will have that discussion. Like most discussions in my family’s history, we don’t get to the hard topics very well. Instead, we devolve into chats about sports or the weather or other trivial crap. But getting the disposition of the house sorted out would go a long way toward me being able to sort out my next steps, and that would go a long way toward clearing up the taking-to-the-ship question. THAT’S why all of this navel-gazing is relevant.

And I realize that by posting this here for all the world to see I might be jeopardizing my employment prospects with some of the mentioned entities, but I’ve been trying to be more open with the issues and challenges in my life, and this whole ball of wax is THE issue and challenge in my life right now. That’s why I’ve barfed it up onto this page and I guess we’ll see what happens. I will, of course, keep you posted.

And in the meantime, I’m going to try to log some sail time (if the weather here in the Mid-Atlantic would cooperate) and get back to writing in this space about Further (I actually DO have a good story to share about Further…another time) and boats and sailing and boat life. Thanks for indulging me and stay tuned.