Building, connecting, and questioning my way to meaning

July 5, 2020
10 min read

Recently, I’ve been thinking a lot about how I should think and act to steer my life in a purposeful direction — “maximize the potential of your life,” as TKS co-founder Nadeem Nathoo puts it.

Four months ago may have been the peak of my life so far in terms of feeling like I knew what I was doing. College apps had been turned in. My grueling 20-hours-a-week tenure as Executive Digital Editor of The Phillipian had come to a close, my two major initiatives — rebuilding the website and launching a live broadcast news show — carrying on strong under the new board’s leadership. I had made it through all the required and perquisite classes, picking up a love for the humanities in the process, and thoroughly enjoyed the various electives I was taking. I embarked on an independent research project and was selected to present a TEDx talk. I gave up my phone for 72 hours for a philosophy class assignment, and didn’t take it back until I left for break — I no longer needed anybody to tell me what to do.

As I wrote in a blog post two months ago, I held that “the purpose of my life…is to continuously learn and think and seek out a larger meaning.” Being on Andover’s campus validated this, rewarding me for engaging indiscriminately with all disciplines and directions of classes, clubs, and people. I was a leader and changemaker within campus organizations and its community, but not beyond — there was so much to do and learn within the campus, there was no reason to really extend beyond it. If I had continued on the ideal trajectory, going on to an elite liberal arts institution, then grad school or management consulting or whatever after that, I could have continued to find fulfillment from this mindset, forever accumulating knowledge, intellect, ability to lead. Yale professor William Deresiewicz calls this the “paradox of potential” in his book Excellent Sheep, criticizing elite educational institutions for creating a culture of stifling original thought and seeking of individual purpose. I don’t entirely agree with his judgement on the matter, but he identifies the same kind of semi-insulated, philomathean bubble that I was in at Andover, and didn’t intend to leave behind.

This bubble began to thin away, however, when my college decisions came out. I had planned to double major in English and Computer Science, but ended up committing to Georgia Tech, a school that was amazing for CS but didn’t offer an English major at all. Moving forward, seeking excellence (i.e. through CS projects and internships) would require specialization, not idealistic exploration. The course of my life suddenly felt deeply derailed, not because my specific prospects were changing all that much — I planned to major in CS wherever I went, after all — but because the value system on which I had built my understanding of myself was no longer viable, and I quickly began to compensate. “I had often looked forward to college being a confident fresh start, the continuing growth of my potential and self,” I wrote in my senior reflection piece. “[Instead], it seemed like it was once again time to humble myself, just put my head down and move forward through the uncertainty. I scrambled to apply to internships, programs, whatever I could find. I completely forgot the self that I had previously found.” To Georgia Tech, I submitted an application for deferred admission after a gap year.

Faced with uncertainty, I fell back on the tools and frameworks I knew best. The first of these: “do to learn, not learn to do.” This is one of my longest- and deepest-held principles, learned from my dad pushing me to learn outside of class as a kid, to found clubs and design my own experiments. As a middle schooler, I taught myself filmmaking and web development by running a tech YouTube channel and constantly iterating on my personal website, respectively. From project to project, iteration to iteration, I continuously added new techniques and used new tools, building my skills and polishing old ones. My ability to learn quickly and endless raw self-initiative helped me provide value wherever I went: as a graphic designer for a political campaign in ninth grade; the founder of my robotics team’s media team; the Executive Digital Editor of The Phillipian, chosen with minimal prior experience, but abundant vision and drive. I was frequently validated for this trait, gaining leadership positions and success not by grinding the “traditional way,” but by my own initiatives. Unsurprisingly, I began to rapidly build and learn after my more recent moment of crisis. I had attempted to learn d3.js multiple times before, but now I bashed out an entire customizable charting library that was deployed on The Phillipian’s State of the Academy project. I had long been terrified of React, but blitzed through all of serverless-stack.com in about a week and a half, starting work on a full-stack webapp right after.

My self-initiative was once my proudest trait, my slogan of “do to learn, not learn to do” plastered across my resume and website. By the time I got into Andover, though, I had began to lose faith in it. Sure, doing my own thing led to a good amount of learning and recognition, but I also missed out on a ton of opportunities — things like competitions, research, or even new clubs, that my “do to learn” framework deemed less valuable than working on my own projects within the track I was already on. At Andover, I attempted to contain my urge to create more than nurture it: piling on classes, prioritizing connections with the people around me, pushing myself to stop doing and talking and do more listening and learning. Indeed, in class discussions and late night conversations, I found a new sense of fulfillment and appreciation, which I then built my value system upon. hen the initial thrill from my recent surge of building faded, this same doubt soon found me. The things that I’ve been doing lack focus; no part feels truly meaningful, or like it’s building directly towards something truly meaningful. I wasn’t happy with how I was spending my energy; something was missing.

The feeling of needing to do more was further hammered in when I went to a talk by TKS alum Ben Nashman. Nashman is the 20 years old founder of a wearable biometrics company. He had entered TKS at 16, researching MRI technology and inventing a new MRI technique. When trying to implement this technique, Nashman found that the required hardware was infeasible; but in the process, he discovered a way to measure blood concentrations of glucose and other biomarkers, the technology that he eventually dropped out of college to pursue the development of. TKS co-founder Nadeem Nathoo asked him a question after his talk. “What is the vision behind your company? How will the world be completely changed because of your work?” Nashman answered that these measurements aren’t usually taken until something goes wrong; the vision of his work is to make them beforehand with real-time monitoring, furthering a revolutionarily impactful shift towards preventative medicine. Even if the technology itself wasn’t incredibly powerful or directly impactful, there was a huge vision behind it, and this is what struck me. Nashman was 16 when he entered TKS, starting a journey of just four years to where he is now. I’m 17 now, going into TKS, yet I don’t even know what direction to look in for any semblance of a specific, impactful vision or purpose. How do I begin to find this direction and ensure that I move down it? How do I move from my unfocused, half-finished webapps to actually meaningful learning and building?

The first answer that I briefly came up with was the familiar idea that people and environment are everything. After passion, vision, and discipline, IndieHackers co-founder Courtland Allen names “other people” as critical ingredients to “staying focused.” I had joined a literary magazine as a staff writer before being promoted to Associate Editor and finally Executive Board; I’m on the Board of Directors of a food rescue organization, starting up a branch in New York as well. I pour time into meetings and work for these commitments not because I believed they would be directly impactful or meaningful, but because it allows me to work with people and leaders that I admire. Similarly, even though my CS projects feel like a slow drag, through them I’ve been able to connect with lots of other developers and entrepreneurs, including industry professionals who have offered lots of insights and advice. I reasoned that, just by virtue of being around purposeful and successful people, I would find my own way back to fulfilling work and existence.

This mindset would probably have gotten me where I wanted eventually — maybe just continuously building would have too; but success would either be one-time (give a man a fish…), or resulting from a further epiphany, as confronting and taking charge of myself in my new reality seemed to demand new, deeper ideas. I didn’t have to wait long to stumble upon a hypothesis for what this new idea might be, though. In the same talk that had heightened my crisis, I was able to find one.

In his talk, Ben Nashman had emphasized the importance of being in an environment that nurtures your innate curiosity. At first, I had just brushed this off as, “oh yeah, environment and people are important, I’ve heard this before.” It wasn’t until a few days later that I processed the second part of what he had said. I read an amazing blog post by Laura Deming titled “Advice for ambitious teenagers” that put it in a more dramatic way: “Question everything.” She points to Isaac Newton’s notebooks, in which he wrote questions like “what is heat?” and “what is light?” These seemingly oversimplistic, or unworthy to be pursued, questions, are what lead to Newton and other mathematicians’ and scientists’ greatest discoveries.

Reflecting on my own past year, I find that these kind of questions are at the root of my most fulfilling experiences. “Inside this box is the meaning of life,” our Existentialism teacher told our class on the first day. “If you open it, what do you think you’ll find?” This unanswerable question, “what is the meaning of life?”, lead into the weighty and intricate of Dostoyevsky, Kierkegaard, and Sartre, that have shaped my understanding of existence and life ever since. Similarly, for an independent research project, my main question was: “what does it mean to be Asian American?” It’s a terrible, terrible research question. It has no scope and reflects zero background research. Yet, fixating on it, reading without immediate aim about Asian American history, ethnic studies, and whatever else, was a revelatory experience, leading to me beginning to understand America in a totally new way, to understand what systemic racism and race itself actually mean at a much more meaningful level, knowledge that has proven itself incredibly important in the past few weeks.

My hypothesis, then, is that this innate curiosity is what drives human innovation and progress, or at least is one critical component of what does. I’m reminded of something I saw in an interview of Susan Cain I edited for my literary magazine just last night: reflecting on the performative nature of today’s youth art/literature world, Cain encouraged artists to create something that they never want others to see. Art is about revealing deep truths, she said, and isolating yourself can be a way to better access them and bring them out. The kind of purpose, meaning, and eventually impact that I’m seeking is no less a form of art. Though external frameworks can help, the root source of accessing the deep truths that lead to meaning and progress is ultimately our purely internal and fundamentally human curiosity. There must be a question at the foundation of every meaningful endeavor, though it may only be found once it has been started. This explains why going into Ethnic Studies or sociology or some other form of humanities academia strongly appeals to me as a way to lead a meaningful life; it explains why, though I’m building and learning so much each day, I struggle to find fulfillment in my CS pursuits; or why, though I’m connecting with so many amazing people across the organizations I’m a part of, I find myself questioning if my time would be better spent elsewhere.

This framework doesn’t lessen the importance of building, learning, and connecting; rather, it offers guidance on how to do so in the most meaningful way possible. Working off of questions that you care about provides you with vision and passion, half of Courtland Allen’s aforementioned four key ingredients to focus. For a bad stupid question, either vision or passion may falter, but that’s okay, you’ll know when it happens and can move on. A good stupid question, on the other hand, will provide the strongest possible forms of vision and passion to drive your work. For building and learning, this framework tells us to do so in service of questions that we truly care about, that are stupid, naive questions coming from a place of internal curiosity, for this is how we find deep truths, original ideas, meaning, and progress. For connecting with others, I return to Laura Deming’s blog post: “Find the best person in your field. Grill them relentlessly on which problems they find interesting.” The way to get the most out of your peers and mentors is not by seeking partnership or advice in relation to your own trajectory; rather, it’s to access their innate curiosity, what they care about most, the deep truths that they have spent their time and energy unearthing.

All said, am I going to re-evaluate everything I’m doing, purging everything that isn’t rooted in worldview-challenging questions and relentlessly chasing the deepest ones I can summon in myself? Of course not. One complication is that I still don’t know how to do this well; this framework is a value system, not an instruction manual. I’ll keep following the principles that I now view as a little less fundamental, building and connecting my way forward. But innate curiosity is something I have a new appreciation for now, and will try to nurture deliberately: I’ve started a Notion page just for writing down questions, big or small. On my list right now: “How are quantum computers programmed?” “How do we prevent or alleviate causes and effects of climate change?” “How do we make meetings not a huge waste of time?”

I’m not sure if what I’ve written here is actually grounded or useful. Perhaps a year later I’ll look back and find gaps and false assumptions. But that’s okay! Life is complicated, and continuous learning is a crucial tool for getting through it. The purpose of this post is for me to document my journey and thoughts for myself, and to have something to share out for feedback and for others to better understand me. For now, then, I’ll be attempting to question my way to meaning!1

  1. I tried to write this blog post as soon as I had this sequence of realizations. I spent the majority of two days with this as my priority task, and utterly failed to make progress on it, instead just getting behind on all my other writing and deadlines. This writing only came together accidentally, a rough draft accidentally emerging in an email to TKS New York director Hayley Caddes. I’ve been putting off some other work to do this, but oh well, it’s done now and I’m really glad that it is.