Crew: Andrew, Lena, Neil, Sergey
Heavy Rain |
Parts of boston were still hiding under heavy fog by the time we took off but the rain had stopped. Andrew is always happy when sailing. |
Minot Light |
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Exploring Scituate Harbor |
The first half of the year was difficult for me, leaving me feeling burned out, anxious, and overwhelmed. Although change is inevitable and this wasn't my first rodeo dealing with uncertainty, 2025 was different. I had been stressed and anxious before, and usually, I could process it and manage it by meditation and journaling. This time was different. This time, my usual tools weren't enough, and the stress and anxiety manifested themselves physically. Fortunately, caring colleagues took care of me and that situation got resolved. That was the headspace I was in by July 2025: knowing that my usual way of dealing with stress might need an upgrade, but not knowing exactly how.
This time on the boat, I've been confronting my own fragility. It's one thing to have a moment like that with people I know and trust—I'm incredibly lucky it happened where it did and that I didn't get seriously hurt. But it's unsettling and nerve-wracking to know it could happen again, anytime, anywhere, without warning.
We debated for a while and then tried another yacht club and got the same message—their launch was only for guests. When I explained our dinghy problem, the exasperation in my voice must have worked—the young man on the radio caved and said he'd come get us since we were stranded. Success! We were soon on our way to town in his launch. He was a nice guy and earned a good tip.
Our main goal was to visit the lighthouse, since it was under construction the last time we were there. It was super clean and beautiful. We then went into town. I still hoped we could find a way to fix our dinghy pump, but others were less confident. We found little more than a CVS and no hardware stores with boat equipment. There was also some sort of carnival going on, but our only interaction with it was watching a guy covered in puke come to the harborside looking for a place to clean up.
The carnival |
I’ve been feeling a lot of shame about that May stress-related incident. For a long time, I've been the "let me sit over here with my problems and be invisible until I solve them" kind of person so you can imagine how difficult it is to realize that I've made others around me feel uncomfortable.
Shame, I learned recently from youtube, is a shield we create because we were led to believe that our true self is inadequate—that we are so broken we have to hide from others at all costs. Shame is also a habit; it gives us something to do so we don't have to deal with the need to grow... Like a lobster that has outgrown its shell and needs to grow a new one. But pushing through it and remembering to look at it for what it is takes effort. So on that day on the boat, I accepted shame as a thing that I need to outgrow, and I made an effort to remember that it does not need to shape my reality.
Way too often, on top of this shame, my subconscious has an urge to build a persona that it wants others to see. My subconscious works hard to protect me from pain. And that's why I am so incredibly grateful for the people in my life who, every once in a while, see right through that persona. They reach the true self and gently remind me: you are not worthless, you are not broken, you can ask for help. When that happens, the mask melts away. It always feels unsettling and uncomfortable for a moment, but that discomfort is how I know it's real. So that day on the boat, I revisited my shame, not as a wall, but as an old shell that needs to be discarded, and to learn to sit in the discomfort and vulnerability of growing up.
The fog was thick as we got going around 7 AM, heading toward Provincetown. |
The true highlight of the day was spotting whales. |
The fog cleared as we approached Provincetown. |
Sergey probably contemplating what needs to be optimized on the boat next. |
Love cape cod |
Entering the Marina |
Our arrival in Provincetown was uneventful. We grabbed a mooring next to the fuel dock and, for the first time, tested our newly inflated dinghy to get to shore. We walked around for a bit, looking for a place to eat, but the main streets were packed. We eventually found a great spot a little closer to the shore – Pepe’s Wharf – that not only had space for us but could seat us outside. Provincetown, as always, was awesome. As we were walking back to the boat, we had to laugh at a banner hanging over the main street that read, "Make America Gay Again."
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While we were underway, we dragged our now inflated dinghy behind us, and it was surfing our wake. It was fun to watch. |
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The Provincetown Marina is awesome - this was the second time we stayed there and between location and the firepit, it was hard to leave! |
When we're sailing, Neil always asks if anyone wants to take the helm. While I'm out there with the guys, I never think, "I wish I could take the helm." I'm usually lost in my own thoughts, trying to stay present instead of letting my mind wander into its default state of worrying all the time. It dawned on me that I'd had very little helm time the day before—barely an hour. Why do I give up the helm so quickly? Why don't I volunteer to take the helm more readily? The question 'what's wrong with me?' always sneaks in too. That was the topic of my meditation on day 2. I want to help and be an equal part of the crew, but I often don't volunteer. "But why?" I wondered. I suspected it had to do with self-worth.
The events of the spring and summer forced me to look closely at my habits at work. I realized I had started diluting my time in ways that didn't support my core goals and values, often letting myself be pulled into meetings and commitments that I didn't need to attend. It was easier to let go of my power in certain decisions, possibly driven by a subconscious fear that protecting my time might trigger the kind of stress that caused the May incident. I know the connection is irrational, but that is what my body was feeling.
Decisions require mental energy. And when I am feeling overwhelmed, the last thing on my mind is to make a decision. Yet, I realize now that the only way to reduce the overwhelm, the only way to handle it, is to decide: this is what I am going to work on right now. Regardless of what demands are on my plate, I still have to make a decision from moment to moment, day to day, week to week. I cannot be successful at building something if I am not a good steward of my own time.
It takes belief in oneself and courage to make decisions that affect others. And taking the helm does include making decisions for the whole crew. So at that moment, I made a decision. And took the helm.
Then somebody noticed (probably Sergey) that the wind was just right for some spinnaker action. And off he and I went to set up the spinnaker. It was a nice shade of blue and white, and it flew us toward Rockport. We had hoped to see whales since Stellwagen is known for its whales, but no luck this time. It didn’t matter; we still had a very enjoyable sail and fun with the spinnaker. Nothing much happened this day other than happy sailing and mucking around with the spinnaker.
Somebody (probably Sergey) noticed the wind was just right for some spinnaker action |
The realization from the day before… that I need to take control of my decisions and ensure my time on this planet is well utilized and the investments that others have made in me are well stewarded... struck a chord with me. During the trip, the conversation drifted into AI, as it tends to happen when a group of people watching the world spin notice the tremendous implications something like that can have everywhere. But at the same time, it’s worrying—I’ve been using more AI to do things like draft emails, get me started on a presentation, or “vibe coding.”
That in itself is not a problem; it’s that the effort to understand and look carefully at the code that was written, or the structure of the text, is high. When I used to write research papers, every word was measured; I would form the message in my mind before I wrote things down. My English is not the best, but at least I was able to create a consistent message sentence after sentence, paragraph after paragraph—one that flowed from the previous sections.
Before LLMs, I often dealt with the anxiety by regularly reminding myself of the TTT: Things Take Time. Now, with conversational AI, it’s different… I lose my patience very quickly because "Can't AI just do it?" The LLMs often create a wall of text or miss the message I am trying to convey. I spend a lot of time telling the LLM what’s wrong with its answer… but it's not clear whether that time is well spent. Am I teaching the LLM … or is LLM teaching me. Anyway, regardless, the main conclusion is: I need to take back my agency and decide how I am going to use my time from now on, and what decisions I will make rather than let them be made for me.
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I barely remember the morning of day 4 but I remember that Neil brought out the drone and now we have a beafutil 360 flyby of our lovely boat. |
We caught some seaweed with our anchor that needed to return to the sea |
We sailed happily and enjoyed the morning sun for a while and then the fog came back... we saw some ghost ships, blew the fog horn a few times and while we were at it, we crossed some state lines: first New Hampshire, then Maine.
Fog rolled in and we could not see anything |
I remember at some point we sent Sergey over to the bow to set up a jibe preventer, which in Sergey's world means a line attached to the main sail on one side and a stenchion on the other, preventing it from accidentally jibing and hitting someone in the head. However, it also prevents us from jibing on purpose when we are approaching land and need to change directions. The moment I remember was Sergey happily enjoying his lunch and Andrew screaming, "Stop eating, we need to jibe!"
Islands emerged out of nowhere. We then saw another sailboat |
Finding a place to anchor for the night took all of our attention. |
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The lady can stop us from visiting the island but she can't stop our drone :D |
Our dinghy in Smuttynose Island. |
We had been warned by a family having dinner that the seaguls might nose dive. We didn't want to risk it |
The famous drone. Which birds and seagulls hated. |
My thoughts that day kept coming back to the horizon, or the lack of it. Could that also be the reason for all the doom and gloom I have been feeling around AI? Not even the people at the top—the ones with the "radars" and the tools—can really see what’s next. It’s just less fun when you can’t see where you’re headed. But we’re caught in the middle of it anyway; we just have to get through it.
Going back is definitely not an option; that would just mean returning to the same conditions, or worse. So, I guess you just have to push on. Keep going based on the chart, trust that land is out there, and trust that other boats (ie. people) will see and hear us, so we avoid a collision (ie. abandoning our goals and letting AI define our goals).
Mirages are also a possibility in both scenarios. You want to believe in something, that AI will make you more productive, that land is close by. But looks are deceiving. And sometimes mirages can be more dangerous than the fog.
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Drone based reconnaissance |
We executed a clean sail off the mooring with a nice, precise tack. We didn't need to steer much for a while, but we did have to keep a sharp eye out for lobster traps, which were everywhere. This was Maine after all (or close enough). No point in getting angry.
Visitor from another boat |
We actually didn't need to steer much for a while, only small nudges. |
We reached Newburyport, docked for a bit, visited the city, provisioned and had lunch. We needed to pump out, but there was no pump-out station where we were docked—sometimes this happens. There was some issue with the water pressure. This offered an opportunity for an interesting side quest: we had the opportunity to go under a bridge to find another pump-out station. The bridge was open, and we just had to radio and ask them not to shut it, which they had already started doing. It forced us to adapt, and we got the job done.
And so, we just make other plans, much like in life when something we need and hoped to find in a place isn't available.
The bridge was open, and we just had to radio and ask them not to shut it. |
Then, with our bellies full after lunch and our boat pumped out, we set sail to Rockport. That’s when the tacking back and forth began because we needed to go south and the wind was blowing from the south. The ocean was wide and blue, and we were forced onto a wrong heading. Now that we were well fed, the boredom of holding the wheel seemed a little more bearable. It became a constant need for a small nudge to make it go left when the winds and waves pulled us to the right. Long passages require this discipline of small nudges. I learned this a long time ago: one of the most important lessons is that moving in the right direction is often just about ensuring we’re nudging the wheel ever so slightly. Just like in life, it's about making small corrections when things drift too far in one direction or the other. To break the boredom, we looked out into the vast ocean hoping to see some spouts that would interrupt the monotony, but of course, there were none.
Wild whales do not respond to our desire to be entertained!!
It was after dark when we returned to Rockport. |
It was after dark when we returned to Rockport. The lobster traps, which were annoying nuisances earlier, now became a serious threat. The crew grew more alert as darkness fell completely; we couldn't see where we were going. Echolocation would have been nice. We anchored safely after avoiding a couple of traps we didn't see until the very last minute.
We finished the day with grilled fish. The night on deck was clear, the fog a distant memory.
My mind keeps going back to work even when there’s nothing urgent on the boat to worry about. The way we deal with lobster traps on the boat reminded me of the traps we all face in life—like difficult situations that can’t be wished away. There is no point getting angry or frustrated about them; you just have to accept they are there and deal with the constraint they create in your life. Just as on the water you adjust the rudder left or right to avoid a lobster trap, and then return to your course, even though the optimal path would be to keep steering in the same direction, you sometimes need to steer away from the optimal path at work to avoid getting caught in obstacles and traps.
I found myself looking at the fancy houses lining the banks, idly wondering what it would be like to live there, and which one I would prefer. The river was long and lovely, though the current was strong.
Anisquam River floating homes |
Would be fun to live in one of these houses along the river |
Open up please. We would like to pass. |
And then, the crossing was over and we existed near Gloucester and picked up a mooring near Half Moon Beach. We jumped in the water, had lunch, and watched lots of people on the beach. Which made me remember that I had brought my snorkling gear. I'm not the bravest when it comes to going deep under water... I have long subconciously feared the imaginary monsters that lie under the surface. My mother used to have to drag me to the water at the beach because of said imaginary monsters. I had to remind myself: "feel the fear and do it anyway." And so I did. And I saw crab and starfish (no monsters).
Lots of people on the beach + Pretty boats in Gloucester harbor |
After lunch, we attempted to sail toward Misery Islands but had no luck—the wind simply died. This frustrating moment presented a decision: keep trying to steer on a frustrating zigzag course, or motor. We went with the motor. We were lucky enough to have that option, and there was no need to exhaust ourselves or become frustrated at something we couldn't control. We quickly made it to Misery Island, grabbed a mooring, put a line through the hook, and went snorkeling again. It was a rather long snorkel, but less visually interesting than the one at Half Moon, though the underwater kelp forests are not to be sneered at. I did spot a hermit crab on a shell, which proceeded to scare another little crab. I followed it for a while until it hid. It was one of those random occurrences—a small, minor detail—that, nevertheless, makes the texture of a sailing trip memorable.
That evening, we enjoyed wine and sunsets before taking the dinghy ashore for a trip to the island, finding the ruins from another life. The row from the boat to the island, putting on a show for all the other boaters watching, was entertaining. One nice fellow, ready to leave on his motorboat, waited and let us pass, calling out, "I got you, Gilligan." Everybody was generally in a good mood; that is the beauty of boating, where people are typically swimming, drinking, and enjoying the communal buzz.
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"I got you, Gilligan." |
The night sky was quiet and full of stars—the first time this trip we had a clear view of them. I promptly fell asleep right there in the cockpit, drifting off as a line from a Coldplay song came to mind (... I think I see you...)
Ruins and lovely sights |
Los amigos and sunset |
Good morning, Sergey! |
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Neil sent the drone on a scouting mission to check out the nest of seagulls. The sea was ultra calm... |
We cast off around 9, beginning another sailing run. This time, we broke the monotony of the passage with a conversation about books-true nerd stuff, specifically Sci-Fi and discussing concepts like vacuum decay and the various ways the universe could ultimately end. It certainly helps having a well-read crew for these stretches. We had drunk to luck the day before, and luck was on our side once again. The sailing was almost done, with decent wind carrying us toward Boston. Before lunch, we decided to head to Spectacle Island and anchor there. We ate the remaining cheese and turkey, along with some veggies, and had a final swim. We then motored all the way to the fuel dock, where we pumped out and refueled. From there, we motored over to the Boston Sailing Center (BSC) with plenty of time to spare, having made excellent progress that final day.
It's probably fitting that I write this blog post close to the end of a chaotic year. A time when we normally reflect on what went well, what could have gone better... This trip went super well. No head problems, no broken lines. The dinghy pump absence was our own fault; we could have checked, but it was quickly remedied thanks to the harbormaster at Scituate (thanks again).
I love, love, love sailing with this crew; it's a good mix of adventure and comfort making for a perfect blend of fun. No other major health events since May, and hopefully nothing more will happen for a very long time. And if it happens, oh well. Now I know I can deal with it.
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