I finally left the dock and Mahon for good. I really needed to do that, I was going a crazy there. I even found a rat on the boat, it ate part of Slick. I stayed a few more days to see the horse festival, and these are some pictures. I don’t particularly want to talk about the horse festival other than its a full-contact fiesta where horses are ridden through crowds of people in a wild manner. The caballeros rear the horses up and the pomada-drunken crowd touch the horses front legs and stomach for luck. The longer you can hold the horse up the luckier you are. OK, I touched a horse’s stomach, I wasn’t in any shape to hold it though. Leaving the dock made feel I was a captain again. I need to be, I have an ocean to cross still. This is going to be a long blog post.

I want to focus on what it means to be a captain of a small boat in a big ocean. The psychology, I think, is different than the average land-lubber. So I want to try to elaborate on what that is and how I got there. I certainly wasn’t born this way and even when I left I was not really a captain. I thought I was, but I wasn’t. I know three different boats in the last week who have either decided to sell their boats or ship them home because they didn’t want to do it anymore, mostly thanks to stress from weather. I understand that, I’ve been there for sure. For a different but similar take on captaincy, see Cresswell Walker’s book, “Sailing the 7 C’s”.

So, what is the difference in terms of the reality of my day that makes me think I’m any different than anyone else? I think the primary thing is the peak-stress level. Yes, I sit most days with my feet up and a cocktail in my hand in some gorgeous foreign land after a fantastic day of sailing. That’s the image anyway, and its partly true. What this image doesn’t portray is the stress involved in pushing your boat around the world. Most people, land-lubbers, have stress. I’m not saying they don’t. Few of them, though, have ultra-stress. The worst things that happens to people in a given day is perhaps losing some (or a lot of) money, losing a job, perhaps divorce or dealing with death. But they don’t get in their car and think “OK, if now is not the right time to drive, I will have to deal with severe consequences,” No, they just buckle their seat belt (actually in much of the world they don’t even do this) and go. When they get home, they don’t have to check the weather to make sure their house is in a safe location, it probably just is. And if it isn’t, well, accidents happen, but there will be help.

A skipper has to deal with this and have it on his mind every moment of the day. Every anchorage you stop in, every passage you plan, every choice of crew, every upgrade to the boat, everything you do, has a consequences that involves loss of ship and loss of life. And you have to be able to deal with it. You have make choices, usually none of which are from a list of good ones. Your crew and your boat count on you not to mess this up. When you are in the middle of the ocean, help can be days away, if it even comes. You can’t outrun the wind so you have to deal with it. You can’t shut down, you can’t pull over and park, you can’t say “that can wait till morning” you just have to deal with it. What is this IT that you must deal with? Well, IT can be an anchor dragging onto a lee shore at 3 AM in a massive thunder storm after a long passage, IT can be a medical emergency at sea during a period of large swell, IT can be cyclones that you just can’t out-run, or dealing with major material failures like the loss of a mast (or worse the keel). IT happens, you try to remove all possibility of IT, but IT happens. And you have to have that on your mind at all times and make decisions to prevent IT or deal with IT when IT does happen. Just to make it worse, IT usually comes when you are tired, hungry, cold and fatigued maybe even to the point of hallucinating.

There we go, if you think that I am making up the idea of ultra-stress, when was the last time you had to deal with a compounded major event at work or at home while you were hallucinating? I want recommend three books to potential ocean going captains out there. No it isn’t the The Venturesome Voyages of Captain Voss or The Long Way
or Sailing Alone Around the World or any of that. Those are great books and they will inspire you and when you get somewhere that is discussed in those books and read that passage again it takes on new meaning. But the ones I want to recommend are ones that tell you what the IT is that can happen, how bad IT can get, and how fast IT spirals out of control. They tell you how to deal with IT as well, but until you actually are dealing with IT, you don’t know if you can. So, the books – Adlard Coles’ Heavy Weather Sailing by Peter Bruce, Advanced First Aid Afloat by Peter F. Eastman and John M. Levinson and Adrift: Seventy-Six Days Lost at Sea by Steven Callahan, and if you can imagine yourself, your boat and your crew in any combination of situations from these books (IT always come in combinations) then you might be ready to be a skipper on a blue water sailing boat. If you want the ultimate freedom of captaincy then you have to be able to deal with the responsibility and consequence of choice, with no safety net or perceived security. If you screw up the responsibility and dealing with the consequences – its over.

Most people think they can do this, but they can’t. Which might be why they never actually try. So if you made it this far in my post without thinking I am some sort egoist, then please read on and I will explain how I got there. I certainly wasn’t there when I left, I thought I was but I wasn’t. I want to select a few life lessons that helped me become a captain. Some are funny, some are personal, some are tragic, but in the end they all helped me grow.

I remember my third time skiing. That was the first time I ever went down a black diamond. Black diamonds in the west are completely different than blacks in the east, as in the eastern ones are really blues. Anyway, it was a little pimple of a mountain in Eastern Washington called Bluewood. I went up for the day with three other friends who were good skiers and were going to help me get better. At some point, we stopped and looked down the steep face of the hardest run of this hill, Jackhammer. To me, it seemed a snow-covered cliff with speed-bumps in it. Why would I want to go down that. Two of the skiers were very good and dropped in and took the moguls with ease. I looked at the girl next to me, also a much more experienced skier, she could see my hesitation. “You’ll never get better if you don’t do it, Tim.” With that she dropped in and fell at least five times down the hill. I’ll never get better if I don’t. I think I fell the entire way down the hill, bouncing off moguls, leaving things behind, just making a general yard-sale of ski-gear. Did it hurt? Yes, a lot. But did I come off the bottom of the appropriately named Jackhammer a better skier and more confident person? Yes.

A few years later my life was kind of shitty. I failed out of college, I was living in my brother’s basement. I realized my life need to change. No one was going to change it for me. I had to take responsibility and do something to improve it. I was 20 at the time. I remember being stuck in traffic and looking over at the military recruiters and then looking ahead at the hot Eastern Washington pavement, the traffic and my overheating car. Then I look over at the Navy office and there is a chief leaning against the wall in his dress whites holding a cigarette and a coke. I looked again at the traffic ahead. I took the last possible turn into the recruiters block. Eventually, after taking all sorts of tests and things, I qualified to be a nuke, and I volunteered for sub-service. I made a choice, I took control of my life. That single choice changed my life. The schools were harder than anything I had ever done before, of the 22 in my first class that started, less than 10 of us made it to the fleet. This was were I learned that not everyone has the capacity to do everything that anyone else does. Some people fail, they need to go seek life elsewhere and succeed there. Not everyone earns a blue ribbon, or a red or even white one for that matter. The last thing the recruiter said to me, after explaining how hard of a path in the military I chose was – If it was easy, everybody would do it.

After 6 years in the Navy and almost a year of life underwater in an intense and difficult environment working as a reactor operator on a submarine, I understood stress. And I understood how to deal with it. I had 140 brothers to help out, but as we say down there, all of us surface or none of us do. The education, skills and training I received in the military where more than just academic. I learned how much suck I could deal with, and how much stress I could deal with. The answer is a lot.

I don’t know why I ever chose to sail around the world. I’m not sure where I even got the idea. When I bought Slick I had only sailed a few times, I really had no idea how. In my first semester in grad-school I got divorced. This happens to submariners, even after they get out. Anyway, for some reason, probably an escapist idea, I wanted a boat, and I wanted to sail around the world. One night, I was meeting some friends in a bar. One of the guys I had never met before, we will call him “Steve.” I told him I wanted a boat and to sail around the world, it turned out he was a very experienced racer and we agreed that if I bought a boat I should call him.

I called Steve 9 months later. I suppose Steve gets calls 9 months later from people he meets in bars all the time, but for a different reason. I bought Slick, and I thought he should come have a look and go on the first sail with me. Especially since she was the biggest sail boat I had ever been on. We went out into Buzzard’s Bay, sailed about and came back to the most beautiful harbor in Massachusetts. Steve tried to convince me to race the boat. I just wanted to get it back to Boston in one piece. My ex-girlfriend and I took Slick to her new home. And Steve spent the rest of the fall teaching me how to sail, we got out as much as we could.

The next spring we went to a big party in Hyannis where a sail boat race breaks out called Figawi. The race is across Nantucket Sound to Nantucket Island. Anyway, the race is not important, its the delivery home where the lesson is. The wind was blowing maybe 25-30 on the cheek. I wanted to delay a day to let the blow go by but the crew didn’t have the time to sit. Well, I will never get better if I don’t, so we put the second reef in and left. I never sailed in anything like that before. Short period, big waves, steep seas in the shallow sound going to windward, we got beat up for 8 or 10 hours on that crossing. I couldn’t handle it, I made Steve drive, not just because I was a terrible helmsmen but because it was beyond my ability to sail in those conditions.

When we got back to Boston, some guys I never met before came over to talk. They also delivered their boat back. The skipper told me he saw boats rounding up all over, two that had to be rescued and at last one that sank. Wow. I didn’t realize I was going into those sort of conditions. I didn’t realize the potential consequence of my choice to go that day. If Steve hadn’t been on board, we very well may have needed rescue too. Steve looked at me at the end of it and said – the boat that is tougher than you are.

I spent three years racing Slick after a season on that other skipper’s boat. This was were I really learned to sail. The first season though, everyone laughed at us. We were terrible, we had no idea what we were doing. My jib trimmer had a winch handle in one hand and a book on jib-trimming in the other. I never actually learned to helm a boat, but it was mine so I was driving. Steve was there, coaching and running tactics. The rest, well it was the girlfriend and whoever I could get from the office to come race. We lost races because we didn’t know what we were doing, the bottom had 4 inches of growth from the winter, my sails were old, and I didn’t know how to drive. I lived on the boat, I was racing my house. It was overweight and I was afraid to mix it up, in an accident those guys lose their toy, I lose my home. The following season I bought a new main sail and took care of the bottom. I had sort of regular crew and we did a little better. Then I bought a racing jib, and a big spinnaker. I had a solid crew that I built over three years and a clean bottom. Every Wednesday and Saturday we emptied Slick of all my belongings. We started winning races, or at least making the podium. No one laughed at us anymore, they were scared. It was great. I then knew how to sail. More importantly, I then realized boats have a woman’s names for a reason. It isn’t because they take lots of time and money, they do, but that isn’t the reason. Its because if you love them and take care of them, they will take care of you. There are wrong boats, and a whole lot more wrong women, but the important thing as a captain, just as a lover, is to take care of her. Then when you need it, she reciprocates. If she doesn’t, it might to time to think about getting new one.

I don’t want to sound arrogant. But after the nuke school in the military, the majority of my grad program at MIT was pretty easy. The math was hard, real hard, but that was to be expected. There was other stuff too that I had never been exposed to but the concepts and the majority of the actual doing, that was comfortable. Part of it was because I learned how to study in the Navy, and part of it was because I entered grad school with a lot of experience in what I was studying. That helps. Anyway, I failed my first PhD qualifying exam. Let’s be clear actually, I didn’t fail it outright, I was close enough to failing that I could be failed if they decided to. And they did. At first I was a bit confused, they said they failed me because of my analytical ability, what the hell does that mean? Eventually I realized that was just the excuse, I really failed because I had upset some people. Well, as they used to tell us in boot camp – if your going to be stupid you better be strong or at least pretty. It wasn’t that I was stupid per se, it was actually that I was just an asshole. A captain has to stay strong, even if he fails as a result his own actions. There is no room for self-pity. You have to take accountability and step-up. Anyway, the following year It was really hard to stay motivated, but I had to be strong, and I passed.

The final thing, and this one is really tough, and I think most people never figure it out. If the boat is stronger than me, how strong am I? This isn’t a question you can answer at a corporate confidence builder or executive-retreat. You find this out at sea, and on battle fields and on mountain tops. I remember getting a phone call one day when I was working in the lab. It was my brother and he said if I wanted to see my dad alive one last time, I had better fly home. I think I was on the next flight. My dad had been dying for years, but it accelerated after my mother went, I think. Anyway, the entire time I was in grad school I always had that on my mind. And then one day I had to actually confront it. Dad had some machines to help him breath and monitor his condition. We watched daily as the machines increased in output and his blood oxygen level decreased. At some point the machines were at 100% of their capacity and his oxygen level was still dropping. This was it. As a scientist it seemed to be a fairly straight forward linear problem. He was going to die, and very soon. The doctors of course, they seem to think it is in the best interest of the family to keep giving them hope. I am not sure why they do this. We realized he wasn’t going to wake up, and after all the loose ends of slow death, like taking care of last minute things, the visits by friends and clergy, whatever, it was time. My brother and sister and I sat there as the machines were removed. They both had their spouses with them. My dad’s best friend was there too. When the oxygen was removed, we thought it would go fairly quickly. The six of sat their watching, crying. It took a long time. Longer than any of us expected. For some reason my father did not just die, he did not go easy. He fought. I had only seen one other person die before, and they just died, nicely, no struggle. He fought and fought and refused. Even though his eyes were closed and he had only a frail body left, he continued in his drug induced sleep to fight. I don’t know if I remember this next part because It actually happened or if in the extreme emotional state of the moment I imagined it. But he woke up and looked at all of us and said “That’s it.” Then he laid down and turned gray starting from his toes. My sister-in-law went and kissed his forehead and closed his eyes.

That’s it. What the fuck does that mean? This devastated me. I fell apart. I had been running a lot, running is good therapy. I was doing it too much though, like 50 miles a week every other week and 35 in between. The day of my dad’s funeral, I ran 20 miles. The next day I flew back to Boston. I ran 15. I just kept running. When I reached 50 miles the next day I realized something. I am going to run 100 miles this week. I made it a goal, I pushed myself. I broke myself. It was physically the most difficult thing I have ever done. I had two running partners. One was the undergrad that worked for me and one was my then-girlfriend. I ran with one in the morning and the other in the evening. It was the fifth day of my personal challenge. I had already run 10 miles that morning. We set out at night to do another 8, 4 out 4 back. The trail, for all you Boston runners was the Minute-Man, we left from Davis Square. As we hit the 4 mile mark I wanted to do another mile, I felt good. At 5 another. My partner, a marathoner, said “remember, every one you do is one you have to do going back.” I felt good. At mile 7 she made me turn around. OK good. That was 71 miles, by the time we got home it would be 78 miles. Good, I can do this. Well, you don’t just go run 14 miles with out a little prep, like water or some snack especially after having already run 10 earlier in the day. I remember very vividly the pain on the way back, it started 3 miles after we turned around. It hurt. My knee, one that had been damaged by being struck by a car several years before, it was felt like it was in vice. My lungs were burning, chest exploding and muscles vibrating in painful weakness, they were trying to give up on me. Finally, at mile 76 for the week, that’s almost three marathons, we reached a drinking fountain, the only drinking fountain, by Alewife. I took a few sips, and then laid down in the grass.

Combat divers, when they are in dive school have something they call “seeing the wizard” this is where you hypoxiate from not being able to breath thanks to the water. It isn’t quite drowning but its close. At the outer reaches of your vision, it turns black and then works its way in till your vision is gone and you wake up on the side of the pool with instructors poking you. This is what happened to me, although it wasn’t quite hypoxia. That’s it. I passed out from the pain. I don’t remember how long I was there, probably just a minute. Then I realized, that was it. That was what I needed to know. That is the absolute limit of my ability, the physiological limit of my body, and psychological limit of my mind over my body. If I was in an actual survival situation, that was the moment I would die, when I could no longer fight. I rested awhile, then limped home. I finished off the last 24 miles over two days. I completed my goal, not just the numerical one, but the one of enlightenment.

So how does this all lead to me being a captain? Like I said, when I left I was not. I remember the last time I felt fear. It was on the way to Grand Inagua, in the Bahamas. We got caught out again, because we made a bit of a bad decision. The waves were big and square and fast. We had no where to run to, except down between Haiti and Cuba, the Windward Passage. Some of the most dangerous waters in the entire Caribbean, at least in that sort of weather. We fought all day and night with this passing front. The auto-pilot was overwhelmed and we were driving. It was pitch black and you couldn’t even see the waves, it was physically and mentally demanding. We were cold, wet, hungry and tired. Sleep deprived, actually. I was having hallucinations. Our lives and my boat really were on the line, based on the decisions that I alone had to make. Do we run, down to even more danger? Do we turn to Grand Inagua, the island we missed, and go to windward? Is Slick up to that? Are we? Neither of these choices are good, both are stupid, so we better be strong as neither of us are pretty. The boat is tougher than we are. But I felt like I was at about mile 75. The stress was overwhelming. There was no getting better here, there was no don’t. I had a choice and I was going to be accountable for that choice, and the consequences of that choice were tremendous. We turned to and made way for the island. We didn’t know for sure we would make it but the other choice would have been suicide. Slick handled the new point of sail well and she was taking care of us. Slick is not really a woman’s name, but she was there when we needed her. I don’t think other cruising boats could have made that point of sail. Eventually, after a a few hours on a hard-tack we got into to the lee of the island and dropped the anchor off a beach, it was like three in the morning. We were safe, we had dealt with IT. Nate asked me – this was supposed to be easy, why were doing this? I just looked him and said – If it was easy, everybody would do it.

I am pretty sure I went in my rack and shut the door and cried. But I was safe, my crew was safe, my boat was safe. Nothing else really mattered. Since then I have dealt with much worse weather and more difficult situations, and made difficult decisions with less information, somewhat regularly. I am a captain and I have a lot of new gray hair and I am still a terrible helmsman.