Kialoa III

There are small episodes in any given day where I catch myself daydreaming the different ways that life could play out. They include what I might do if I had more money, or resources available, the right contacts, had made different decisions when I was younger…and the list goes on. They all express my acute desire for attaining the things that I believe would lead to a fulfilling life. Some of them are reasonable, while others are definitely outlandish. A numerous selection of them are seemingly selfless, and some are completely selfish. As enrapturing as they can be, they are a panacea that vanishes upon the slightest interruption of my thoughts. I then find myself back to the world as it is; not as how I have dreamed it to be. Daydreaming is so enticing because it presents a world in which the impossible is plausible, and the possible feels actual; even if for a brief moment. In a daydream, risk and personal sacrifice are overlooked, if not completely eliminated. It presents the mountaintop view without the need for the climb. Risk is real, but before anything meaningful about risk can be said, a detour must be taken.

I took the six hour train ride down to San Diego to help transport the Kialoa III maxi yacht back to the Channel Islands Harbor*. The owner of the yacht and his family had been there for a week already on holiday, and I was arriving the day before they left. Hearing that the owner and his family were good natured I was looking forward to meeting them. I also had never met anyone who had wealth in the billions of dollars and scenarios went through my mind of impressing him with some philosophical knowledge, shortly to be followed with a job offer that paid ridiculous amounts of money. The seriousness of such thoughts passed quickly from my mind and I laughed at myself. I then turned to the more realistic possibility of saying something completely idiotic in front of him and shuddered as such scenarios rolled through my head. I decided it was best to always smile and keep my comments short. I passed the remainder of the time reading and the train eventually arrived at the station. The weather was a humid eighty-five degrees and the open sky made conditions perfect for sailing. Being picked up by my great friend Alex** we drove to the marina to meet up with the owner and crew. As his wife and son were out shopping, it was decided that we take advantage of the weather and soon pushed off of the dock to tour the harbor. In a friendly atmosphere with more waving hands than chopping waves, we towered over dinghies while overshadowed by much larger vessels; enjoying the day under the bright sun. As the sky was reddening we docked and the owner treated the crew to dinner, being joined by his wife and son.

Daniel, the owner’s son, set the pace of conversation for the night. Two days prior to my arrival he had just gotten over being sick for several days and was in high spirits.  He was just taller than six feet with blonde hair and blue eyes. If I recall correctly he was either turning seventeen or had just turned seventeen. Sitting near him at dinner I heard recounting of childhood antics; he was one who loved to play pranks. He was very talkative and exuded high energy. His confident tone was made agreeable by his earnestness. He was at the cusp of entering university and the possibility being accepted into the ones he preferred were all based on his test scores. He was applying mainly to universities in Europe and possibly some in the U.S. Mathematics and Economics were his two top choices of study. He went back and forth with his father about all of the upsides and downsides of each university and major, weaving in witty comments to make his points in parts where they disagreed. He was also keenly interested in my interests and prodded me clear candid questions. Why was I interested in philosophy? What were its uses outside of academia?  How wouId I make use of my degree outside of school? I answered his questions as best I could and where I lacked clarity he was amicable enough to give me the benefit of the doubt that I was on to something worthwhile. As we talked I found out that he had just about vacationed to every continent and was giving serious thought to just staying in one place for a time. He felt that he had seen enough of the world for now. He asked if I had ever traveled outside of the states and I somewhat sheepishly admitted that I did not even have a passport. Without a trace of condescension assured me that whenever I did go, I would have the time of my life. Conversation boomed as glasses were filled and hot plates were set on to the table. The evening continued as we made our way to the yacht, playing card games that caused roaring laughter late into the night.

Everyone rose early the next morning. We took a quick breakfast and said our goodbyes as the family departed to the airport in a taxi. The crew then made preparations for leaving that afternoon. Out on the water I was looking to the horizon searching my thoughts. I began thinking about where I was in life compared to Daniel. At that point in my life I was certain that I was no longer going to pursue a career in academia. I had just finished reading Antifragile with Ivar two months prior and was convinced that I needed to pursue a different path. While I did not have a clear idea what that would look like, I was sure that Daniel would be successful in any endeavor he chose. To be honest, I felt a tinge of jealousy. I thought of all the great opportunities that he had. In my mind I was running through all of the reasons as to why he had it ‘better’ than me. Few of them were factual but I knew that one of them did not match up with reality. It was the idea that he was living a life without any real risk. It was always in the back of my mind while I was talking to him, but it took an hour or two out on the water to tease out the preconception that I had in assessing the options that life gave him. The sting of jealousy I felt faded after that and here is why.

The idea that affluent people do not face the same risks as less affluent people is real. The idea that they do not face any risks at all is false. What they face are just different risks because they are in a different set of circumstances. Now, I do not mean that the difference between being affluent and not is somehow zero sum and that we are all on an even playing field of sorts. That would be naïve. What I am saying is that it is equally naïve to assume that people of affluence or those born into it do not face any risks in life. Now any person reading this would be more than willing assent to that. However, I contest that in life we do not regularly live as if the above statements are true. Daydreaming is a convenient, telling example. As often as we daydream, I would argue that more than not our thoughts lead to we picking out an individual who has achieved what we desire, or their child who is going to grow up with connections and opportunities not afforded to us. We think that they must have it so good, and confer on them the feelings that we felt in our daydream; that of satisfaction and happiness where risk and personal sacrifice do not exist. Now there are real differences between the types of risks that people are faced with, no doubt.Nevertheless, the small truth to glean is that risk is ubiquitous.

The trip went on without trouble and we sailed back to the Channel Islands harbor within two days.  I am grateful to have met Daniel, and I am still sure that he will succeed in whatever he chooses to do in life. As for myself, I gained a great deal from our short interaction. Walking up the dock and waving goodbye to the crew I was left again to my thoughts. When accepted as true, the proposition ‘risk is ubiquitous’ has numerous corollaries. That it is ‘ubiquitous’ is necessary, but the value of the proposition comes when we begin to examine the concept of ‘risk’ and the concepts closely associated with it.

So what’s next? I have a working idea, and it may take some time to fully plan out and translate content into something that is worth reading. However, I will be sure to post much sooner while coherently organizing my thoughts.


(*)Before it sounds like I have any in depth knowledge when it comes to sailing; I was basically there to hang out and do some light manual labor. Hats off to Captain Smitty and the crew for letting me tag along.

(**)Thanks for making all the Kialoa adventures happen!


Mapping Life Backwards

If you go to the Starbucks on Victoria Avenue in Ventura California any day of the week at just about any time, you are bound to see Ivar. For as many characteristics that would push Ivar to blend into the background of a public coffee shop during a busy hour, there are an equal amount of characteristics that push him right to the forefront. While pushing sixty, Ivar is in the kind of shape where he could do an impromptu triathalon and legitimately compete with those thirty years his junior. He has peppered gray hair styled in a gentleman’s cut that is tight on the sides and is clean shaven. Four out of seven days a week he is wearing a gray shirt, light blue jeans, and Nike running shoes. His large aviator styled glasses frame around his light blue eyes, accented by a slender chin. His demeanor is steady and reserved having been shaped by his past military service, yet his shoulders slouch from time to time. Always earnest, his accented voice projects across the room when he speaks. He is not, however, eager to jump into conversations. You would not notice him, quietly checking his email, until every third person who walked into the store said, “Ivar! Good to see you, have a great day”. Only then would you see Ivar in his corner look up with his light blue eyes and give a wave, adding a faint smile. Ivar is a fixture at Starbucks.

I began frequenting Starbucks regularly at the beginning of 2014. I was not there as often as Ivar, but I was a close second. Life at that time was fairly hectic for me. I was commuting an hour to school five days a week, working two jobs as an English tutor and Supplemental Instructor on campus, and I was an active participant in the Student Philosophy Society on campus that had weekly meetings. I had also just changed my major from English to Philosophy and was immediately falling behind in my Advanced Philosophy of Language course because I was contemporaneously taking a Logic course that; while not required for the class, was strongly recommended. I was finding out quickly why that was. I had a lot of catching up to do in a very short amount of time. When I went to Starbucks I was completely focused on studying, only taking a break every now and then to get a refill for my tall coffee. My interactions with Ivar had for the most part been limited to head nods and short conversations about the weather. That all changed on a particularly busy Saturday morning when I walked in with my laptop and philosophy books and found myself sitting directly across from Ivar at the large table sharing one of the highly coveted wall plugins. I came right into contact with one the qualities I came to most greatly admire about Ivar; his frankness. While his question was, “What makes you think you can just study philosophy?” what I inferred from his tone was something more like, “While I know philosophy gives you a great aerial view of life, how are you keeping your feet on the ground?” That is, where is the pragmatism?

Philosophy to me at that time in life was not just a major; it was a defining part of my identity. All I did every day of was read, think, and write about philosophy. So his candid question definitely put my ego on high alert. I am not exactly sure what I said to Ivar, as I had become very hyper aware of how sweaty my hands were getting from being put on the spot. I do remember that after mentioning that I was working two jobs he seemed satisfied with my answer. On top of that, he seemed genuinely interested in what I was studying. Having frequently longer conversations when we saw each other at Starbucks, Ivar asked if I was interested in giving our talks more structure. I quickly agreed, realizing only after that I would realistically have little time to devote to reading an extra newspaper article or two a week. Ivar suggested we start with a whole book. Now I was really wondering how I would fit that in to my schedule that barely allowed me four hours of sleep a night. It was however, too late to back out. As it turned out, over the next year two years we read and discussed five books. The topics of those books, and conversations furcating from them ranged from economics to political philosophy, contemporary political issues, moral philosophy and religion. The theme weaving all of those topics together was; given what we now know, what concrete changes are we going to make in the way that we live?

I am convinced that the peak, the zenith, of all of our conversations came from the book Antifragile, written by Nassim Nicholas Taleb. The book however wasn’t interested in helping us answer our themed question. In fact it essentially turned our question on its head. That is: Given what you do not know, what concrete changes are you going to make to the way you live?

Antifragile, for me, has become much more than just a book. It has become a project that I am working on and hope to continue for the rest of my life. While I have known that for a long time, I haven’t exactly relayed that message to the people closest to me. And when I try and articulate what Antifragile is about or entails, I don’t really do a great job explaining it. That is probably why most of the major decisions I have made in the past three years of my life have appeared to come out of left field for the people who care about me most. However I think with this blog I can finally begin to explain why I am doing what I am doing. Life is something of a conundrum at times and hard to navigate. As textbook over-thinker my default is to come up with the perfect plan before I do anything. Usually resulting in actually doing nothing. I really like having a plan, but I sometimes don’t know even know where I plan on going. Antifragile, in short, helps you map life while walking backwards without a full plan.

Coming up next: conversations with a billionaire’s son.

Overthinking: Lose Your Excuse

This first post is close to two weeks past the deadline I set. There are six pages of content scribbled on a notebook that cover what this blog is going to be about. I have three anecdotes that aim to articulate the feelings and reasons that motivated me to move from California to Seattle with a bike, a backpack, and a duffel bag. I’m sure they would all be perfect for the start of the blog. The only problem is that I started overthinking, again. Not only are they not perfect, they are not even finished. So this first post is being written off the cuff and will be posted without even checking for grammar errors.

I am a textbook over-thinker. I habitually try and solve every actual and anticipated problem before I start a project. More than not, my ideas rarely make it off the page, and even if they do I rarely follow them through to completion. In fact, I have another blog on Blogger with practically the same title that I “started” about three years ago. To this date, there are zero posts.  This blog is not really even meant to be about overthinking. It is going to be about planning my trip to Italy next summer, documenting the process of getting my captain’s license, espousing true scholarship through praxis, and teasing out the concept of antifragility. All that, of course, cannot be done unless I start writing.

While this blog is not about overthinking, I suppose most generally it is a blog for over-thinkers; with the end goal of providing an example of an over-thinker who is determined to become a doer. As to how I found myself on a train Seattle bound starts three years earlier at a coffee shop with a Norwegian, and his question, “I hope you don’t take offense, but what makes you think you can just study philosophy”.