Chasing the White Whale

Like any individual at odds with oneself and on the cusp of an important decision, I turned to the wise words of cultural icon and professional provocateur Kanye West (heard he dabbles in music as well):

“We at war, we at war with terrorism, racism, but most of all, we at war with ourselves.”

There are too many thoughts – ones I can voice, ones I fall short of being able to express – that I find myself picking one up while dropping another, maybe two. The thoughts, the words that are here though will be real, unadulterated, and genuinely me. To my friends, I hope to take you along with me on this journey – one that is as much mental and introspective as physical and outward.

What I do know? I’m thankful for this opportunity. Thanks to my family and, in particular, my parents for supporting me (financially, emotionally, via international albeit low-tier AT&T data plans) and stomaching the fact that it will be at least an additional six months (Dad, let’s hope the inverted yield curve is lying and recessions are economic constructs) where I remain financially dependent (Mom, don’t worry, your fears of me ending up at a nonprofit are unsubstantiated… for now). Brandon, I know it’s extremely irresponsible of me to leave my your college essays behind a mere month before earlies are due. Thanks to my friends who have believed in me and have implored me to think deeper, to ask the simple yet difficult questions, to walk on the line of the real and pragmatic while still straddling the ideal. A shoutout to my roommates as well for smuggling me in and out of my dorm room in Branford when I illegally squatted there for the one week I was at Yale. Thanks to the precise, palatable positioning of the piano in our reading room at home that really got me thinking more deeply about the juxtaposition of the arbitrariness and intentionality of… hah, no postmodern thought will be explored here (at least not explicitly).

But don’t worry, this isn’t a Grammy’s acceptance speech – that’s all the thanks I have. Truthfully, a semester off is a privilege like no other. There are many who take time off due to situation outside of their control; I had the opportunity to make an active choice out of my own agency. There are few times in life when you can just say, screw it, drop everything and take four months out of your life for nothing else but personal growth. It is among the most selfish and privileged of endeavors, but if this time could fundamentally shape me, impact my senior year and years to come, then is this not a risk worth taking? Perhaps SAT II Math 800 scorer and Palo Alto High School alum Jeremy Lin, known best for rocking awful hairdos and nothing more, said it best in a recent interview, which a former suitemate sent me:

“What I fear most is not failure, what I fear most is not being brave enough to chase my dream.”

Translated from Chinese

There is certainly great irony in this universe, how we read books and watch movies and meet characters who seem absurd, so unlike ourselves, and then time passes and we glance in the mirror only to see we are every bit like them. I feel like Captain Ahab from Moby Dick, which, by the way, change my mind that it is not the American novel – none come close. Ahab is driven by a monomaniacal obsession to hunt down the white whale Moby Dick. But the thing is: nobody else in the novel really understands his obsession, and I wonder if even Ahab himself truly understands it. On one hand, it’s simple: Ahab is driven by revenge, having lost a leg to Moby Dick during their first encounter. On the other, it’s as entangled as a bowl of mama’s spaghetti: Ahab sees himself in Moby Dick, he sees his purpose and meaning, the whale is the intersection of his free will and fate, what Moby Dick ultimately represents is absolutely nebulous. Throughout the novel, members of Ahab’s crew begin to doubt the white whale even exists. You see, Ahab, talks a big talk and they spend endless months chasing this whale, but there are no sightings and not even signs. So am I Ahab? Do I even know what is it that I’m chasing after in this gap semester? Am I chasing something so elusive, so unattainable, so impalpable? Do you have faith or doubts in me in this pursuit?

Let’s break down what I do know. I had been thinking about a gap semester since last semester. I began planning since June, cold emailing roughly 100 working professionals across almost just as many firms, primarily in the LA region. I’d been building up this fantasy of spending a couple months in the investment space in Los Angeles since the end of the semester. I executed – sending follow-up emails (pretty sure I’m blacklisted from Some firms given the obscene number of follow ups I sent), hunting down leads, tailoring firm-specific emails, taking calls and coffee chats – like I was Michael Phelps at the ‘08 Olympics (and I’ve been told I’m an athlete on par with his prowess and talent). But when I received no sensible offers, I felt like Phelps in ‘04. I was hurt, a blow to my ego and dreams – or at least what I thought my dreams were.

Regardless, I had to head back to Yale at the end of August given that I had already booked a flight, which meant I would need to decide in my first few days on campus whether or not I was to take the semester off and purchase a return ticket. The days leading up to my return to campus, I felt awful and torn. I was still empty-handed with no internship. How could I take a gap semester with no solid plans? And to add on more, I felt like I owed it to my parents and myself to make some money first before traveling. In this time, my mom found a column written by an undergrad Jerrica who attends a vocational school in the greater Boston area that you likely haven’t heard of, Harvard, and had just returned from a gap year. So much of her column resonated with me. At one point, she quotes Harvard Dean Fitzsimmons, who actually encourages students to take a gap year:

“Yet the paradox is that the only road to real success is to become more fully oneself, to succeed in the field and on the terms that one defines for oneself.”

Reading her columns triggered a recalibration of my gap semester vision and goals, reminding me of what I was here for and why, despite my empty-handedness, my heart was still so set on a semester off. I had no idea yet how to “become more fully oneself” or what it even meant, but I felt exposed. I realized how much I had tied this idea of a gap semester to an internship, that this gap semester had unknowingly devolved from a deeply complex, personal pursuit to a singular, reductive, preprofessional desire. I realized I was subconsciously looking for familiarity and optimization in this time. Familiarity came in the form of LA, a place I could sell to myself as unfamiliar, but deep down, I knew I wouldn’t grow much nor would it be the kind of growth I was seeking. As for optimization, I knew I intended to use this investment opportunity as a stepping stone into my dream internship for the upcoming summer, yet this semester was supposed to be anything but that. I had been optimizing parts of my life for so long, why not optimize on a different dimension, another axis, or, more daringly, not optimize at all? I realized I had become so enamored by one particular, minute aspect of a grander vision that I not only failed to see the scale and multidimensionality of my original vision, but I also began to forget my vision completely – why I was taking a gap semester in the first place. How often do we walk into situations with our own preconceptions and let them inform our world view and, ultimately, what we do and believe in? Then to realize later that what we’re doing is, in fact, not what we want nor what we believe in, and maybe even the opposite? This isn’t me looking back in hindsight trying to retroactively apply makeup to an ugly situation – trust me, true ugliness is defined by the fact that no amount of makeup can rescue it. Rather, this is me being – oh here comes the word again, guess I lied – thankful for what hurt in the moment but was a blessing in disguise. If I had ended up in Los Angeles, I would’ve loved it, but I never would have found Moby Dick.

I didn’t want to spend a semester doing things I’ve done before or could easily do later, I wanted to spend a semester doing things I hadn’t done before and would have difficulty doing later. I wanted to spend a semester building habits and working on hobbies that I had spent more time thinking about than doing. I wanted to spend a semester reading the books I’ve always wanted to read and the books I’ve never heard of before. I wanted to spend time with family, to record my grandparents’ oral history. I wanted to better understand myself, my tendencies, my habits, my triggers. I wanted to improve traits I already possessed and cultivate ones I didn’t have. I wanted to actively sharpen and define my values. I wanted to challenge myself, to be truly self-reliant, to broaden my horizons and world view. I wanted an education: a deeply personal and dynamic one.

So when I was illegally squatting in my room at Yale, equipped with this refreshed mentality, I realized that this very situation – a lack of concrete plans, an expansive and empty canvas – was exactly what I needed. I needed this lack of structure. For so much of my life, I’ve had all the structure I needed. I pivoted and started reaching out to firms abroad, starting with China. And when things didn’t materialize there, I was bummed out, but I was no longer anxious. I knew an internship would be nice but not necessary for my goals.

I ended up talking over the phone with Jerrica. She told me her story, which helped me move from recalibration to ideation. It sharpened my reasoning, motives, and goals for my gap semester, and it gave me the confidence and courage to take on an indefinite time abroad, solo-traveling.

This mental recalibration didn’t mean all my concerns were over. The days leading up to this solo-travel and backpacking trip, which would be my first, I had my concerns. You might be thinking one of two thoughts: props to me for pursuing something so personal, so meaningful, maybe even noble, or – this is neat and all, but is there any true value in something so outwardly intangible, seemingly impractical, and possibly idealistic? And, listen, I’ve floundered between both. Despite my deep belief in the immaterial, the intangible – too often are we objectified in a deeply subjective world, quantified in our unquantifiable self, enumerated when we are anything but numbers – I spent a lot of time in the second camp of thoughts. Had I fallen into a trap of airiness? Was I pursuing something far too intangible, too ethereal to grasp? Had I been too ideal? Would I be able to survive for weeks using nothing but squat-style Asian toilets?

Almost immediately, these questions were answered. Moments into my first flight, I befriended Austin – a Burning Man frequenter, Nevada City resident, and professional videographer & photographer – and Ade – an Indonesian grandma who immigrated to the US, settled down in the Bay Area in 1979, is a breast cancer survivor, and runs her own travel agency.