Should I Stay or Should I Go? (Public)

If I go, there will be trouble. If I stay, it will be double.

Should I Stay or Should I Go? (Public)
Photo by Boba Jovanovic / Unsplash


I’m sitting in the cockpit under the bimini Jack has rigged like a tent over the boom. Rain is falling in animated circles on the river Dart. I’m wondering what I should do about the trip this summer. I’ve been traveling for so long now that I’m really noticing not being involved in projects. I was happy working before I left, well, happy with my own projects anyway. I don’t want to go just because sailing on a yacht is a popular fantasy and everyone will say, “What? I can’t believe you turned that down.” Of course, it was my own fantasy too.

The idea of spending long hours at sea, being on watches in the middle of the night, and wandering over hill and dale doesn’t hold that much appeal for me at the moment no matter how nice it might all be. What I’d like to do is have more broad human contact after being on Scilly all winter, then go home and sink my teeth back into work.

On the other hand, if there is one thing I can learn from Dom and Jack it’s how to just get on with something. They have a certain “damn the torpedoes” confidence. And lots of laughs would be missed. Is it worth it, the extra three months and effort?

Spending the summer on Scilly would be nice. St. Agnes seems to only filter interesting people to it. It’d be nice to meet some of them, to spend some time there and see what the summer has to offer. I’d like to talk to Jon about all of this.


The weather in Dartmouth is a mess. The shipping forecast will be on in a moment and—I’m sure—confirm the sorry state of the weather into the weekend.

Dartmouth itself has been very enjoyable. It’s a pretty little town set on the slopes around the river. Many of the buildings here have been in continual use since the 1600s.


For lunch today Dom and I took the dinghy on a cruise up the River Dart to Diddisham for a change of pace, munching our pasties (a sort of medieval, English, Hot Pocket) as we went. It was the most beautiful place. Large stone boat houses occasionally showed themselves, peering between the trees that crowded on the water’s edge, and whose lowest branches formed a dense, razor-straight line marking high tide.

Dom and I had fitted the larger motor to the dinghy after we first moored, which enabled us to make this trip at speed—20 knots I’m guessing. The river snaked through seemingly endless forests, passing the occasional house or wrecked barge. We tried to keep to the deepest part of the channel and right before I thought the river would simply run out of water, we hit the town of Totness.

Here, tucked away a reasonable distance away from the ocean, is where the catamaran Team PHILLIPS was built. (The boat I saw being towed in after one of its hulls broke apart during sea trials in Scilly last March.) It was currently back in the shop undergoing repairs. I hadn’t known it was here until the other day and it felt strange to come across it again. Seeing it here in the hangar was amazing. It was absolutely vast. The hulls are 120 ft. long and the boat is 70 ft. wide. I have no idea how they were able to get it into the water, let alone out to sea.

On the way back down river we stopped in a small town, a hamlet really, and went to have a look at the local church. After a quick scan of the interior, Dom slipped through a door at the back of the naive to see what else he could find. I didn’t dare follow. Shortly afterward he appeared in a large window in the tower one floor above me wandering among the bell ringer’s ropes. I motioned for him to come down, my exaggerated movements perhaps picked up by the security camera that I noticed was pointed straight at me. Dom disappeared again to go further up the tower. I waited nervously below feigning interest in the baptismal font and the community news bulletin, half expecting the local constable to burst through the church doors and arrest us for trespassing on holy ground.

It seemed like ages before his six-foot-seven-inch frame unfolded itself from the five-foot-tall door frame he’d previously disappeared into. “There’s no light at the top of the tower,” he said. “I was just feeling my way through the cobwebs.” I felt my flashlight, unused, in the pocket of my sailing jacket and wished I had been brave enough to follow. Why didn’t I? Fear of being caught and told off, I guess. It’s such a powerful inhibitor. I wish I could cast it aside sometimes.


The three of us went ashore to the pub in Diddisham tonight. The weather is still a mess so we’ve been staying put. The shipping forecast predicts cyclonic gales up to force 8 (about 40 mph). That’s no weather in which to be at sea.

I’d almost made up my mind to not go sailing for the summer but we all had such a laugh tonight. Dom and Jack are such good storytellers. Their’s is an oral history.

Jack told us of a dog they used to have when they were doing sailing charters with their Thames barge. Jocko was his name I think. “He was a dog’s dog,” Jack said. “He’d never been on a lead all his life and he did as he pleased. He knew immediately who the guests were for the following two weeks. He’d go with them to the pub and lead them back to the barge at the end of the evening.” One day they were moored alongside a quay near a park where an evening concert was being held. A car pulled up and a couple got out, dressed for the evening, followed by a lovely, white poodle. Jocko was off like a shot. Two seconds later he was on the quay not at all hiding his interest in this couple’s fine pet. The woman immediately snatched up her dog in a huff and told Jocko to shoo as she headed back to their car to put the poodle in for safe keeping.

When the concert was over, the couple walked back to their car to observe this scene: Jocko had somehow managed to climb through the partially open window and had been humping their poodle in the backseat of their Jaguar for the past hour and a half. Even though it was mid-summer, the windows were completely steamed up. We were all laughing ourselves silly as Jack recounted the tale.

After another few pints at a different pub, we stumbled down to the dock in the rain, Jack wearing a piece of cardboard as a makeshift hat, got in the wet dingy, and ferried ourselves back to Elde. Back on board we finished off last night’s stew, which had improved with age, and fell into bed, save for Dom who went back ashore for another couple of pints.


I awoke this morning to the sound of the windlass grinding above my head as it hauled up the anchor. I got out of bed, battened down the fo’c’sle hatch, as Jack had instructed me to do before we headed to sea, and went out into the heart of the ship. The weather had broken. It was a beautiful morning and we’d soon be away.

The light was low and the river quiet as we motored along. I asked Jack the time. “7:20,” was the reply. The plan was to sail to Salcombe which lay around the next head. He said that the seas would still be rough and indeed they were. How strange is was to see whole landscapes sliding towards us. We took them as they came, down one hill, and back up the next.


Salcombe was nice, pretty, nestled down by the shore. We went on a nice walk over hill and dale. Now, for the last couple of days, we’ve been lying in Falmouth again waiting for gale-force winds to pass.

Written in my notes:

Why go?
See the world
Meet nice people
Let Dom and Jack’s no-holds-barred sense of possibility rub off on me.
Stories to tell
VIP ticket to far off lands

Why stay?
Sailing is tedious
Meet my friend Mira from San Francisco in Paris this summer.
Do a poster campaign in Europe
Scilly during the summer
Buy vintage posters in Hamburg

It might be good for me to go but I don’t want to do it just because I feel like I should. Am I afraid of a challenge? No. I just feel like I’m convincing myself that I should go. If I go, and then end up not enjoying myself, I’ll tell myself, “I told you so.” What’s my resistance? Do I know that, ultimately, Dom and Jack’s bravado doesn’t match my personality?

What’s the deal with my wanting to go see Mira? I’ll probably end up getting together with her. It’d be easy to go down that road. I so enjoy spending time with her. And I worry about messing up our friendship.

Maybe I should just go on the trip and see what comes of it. It could be a right of passage, with Jack and Dom as my guides. Eh, maybe I’m a little old for a youthful right of passage. Is that my resistance talking? Could I do three months of bobbing around in the ocean? Sometimes I feel like such a city dweller.