the elitist dichotomy of the sellout's conundrum -- and the hopeful underachiever's solution

a response to sellout's conundrum by Rona Wang on the MIT blog

Parents and teachers who have known Andover students have a peculiar hesitation about recommending kids to go to the high school.

The hesitation isn't related to any shortcoming of the school itself. With a 5:1 student-teacher ratio and billion dollar endowment, Andover's resources -- physical ones ranging from an observatory to a gender studies center -- overshadow those of many small colleges. Details aside, I like to describe the overall feel of the school as a mini elite college: from the classes (Asian American Literature and Film, Existentialism, and Fluid Mechanics are popular senior electives), to the lifestyle (dorms, dining halls, sports, course selection, pretentiously ambitious intellectual conversation), to the $50K tuition (thankfully with very generous financial aid 😭).

Rather, these parents' and teachers' hesitation is caused precisely by the incredible environment of the school: Andover grads often find themselves frustrated and unfulfilled in the world. A friend of mine at Cornell complained that campus conversation wasn't stimulating enough. Friends at pretty much every school except HYPSMs -- the very few colleges with Andover-for-high-schools levels of elite prestige and endowment, you might say -- have noted the same. Even at Pomona College, for which my admitted class clocked a 6.5% acceptance rate, I find myself half-joking about transferring to Stanford or Brown to other "elite overachiever" friends.

These thoughts were on my mind as I read Rona Wang's "sellout's conundrum" on the MIT blog. Wang speaks for a familiar crowd: the award-sweeping, sky-high-achieving students who bend sheepishly to corporate prestige; those who treated high school as "a four-year-long audition" for "Ivies and top state universities and small liberal arts colleges", where they "eventually switch [their] majors to something safe, like economics or computer science". Citing the overachiever canon of William Deresiewicz's Excellent Sheep and Mihir Desai's Crimson "Optionality" op-ed, Wang spells out her fear that she'll lose her intellectual prowess and ambitions and that "by age thirty, we would make six-figures annually; we would have a mortgage, two-point-one kids, and a nice house in a nice neighborhood, and we would have grown into the boring-ass adults we swore we’d never be."

Why not not sell out, then? Why not "pursue [your dreams]" if they "are apparent to you" rather than letting the pursuit of optionality act as "dangerous diversions that will change you" and prevent you from ever reaching "your dreamy outcomes", as Wang quotes Desai instructing?

Because it's hard, Wang says. In fact, it's impossible, endless, unachievable. "I suspect I will spend the rest of my life searching for the words to approximate the secret, untranslatable language of my mind," Wang writes. And why do so? "Because it is the only way I might reach across impossible distances, the galaxies between people."

Therein lies the conundrum. Life is only meaningful when one has "[learned] every secret of the universe" and satisfied their "amalgamation of curiosities and dreams"; "to be a mindful citizen of the world, to do things with purpose," which can never be learned or done through "math psets" or some comparable corporate sellout work. Grounding her commentary in "the real world" via a friend's quote, Wang writes that "vocational skill sets translated into financial stability; excessive, indulgent consumption of literature and sociology papers did not." The latter, and the "meaningful" intellectual exploration the example represents, only lead Wang to being "more lost than ever". "i am a lost child", reads the subtitle of the post.

Yet the tension between intellectual meaning and "real-world" engagement -- a sense of concrete direction and continuity -- only forms a conundrum if the two are framed as inherently opposing qualities of work. True, the tension exists, and the dehumanizing nature of capitalism strengthens the tension even at the top rung of the ladder. Wang writes about trying earnestly to translate her loves for writing and math into concrete work, in the forms of commercial book authorship and finance respectively, but losing her passion in the process. But the movement from observing this tension to conjecturing that "there simply isn’t enough time" to find a sustainable concrete manifestation of meaning is a leaping one. What happens if we take the time instead to walk the steps in-between?

To consider this tension is to ask what Mark Manson declares The Most Important Question of Your Life: "What are you willing to struggle for?" Or more bluntly, "What pain do you want in your life?"

To claim that a truly meaningful life is unachievable is to answer, "there is nothing I am willing to suffer for but my own abstract version of meaning," and "I prefer no pain over the pain of my own self-absorption and pity".

On a personal level, these answers are childishly pouty and self-limiting. If your understanding of what is meaningful in this world prevents you from ever approaching it, then embrace this foundation and embrace the new standards for joy and meaning that are contained within it -- so goes the optimistic atheistic existentialism that Manson subscribes to.

On a social commentary level, the fact that the brightest, best-educated 20-somethings in this country so earnestly experience these conundrums point at the inhumane ways we've come to think about success, productivity, and labor, if in a way that only affects some of the most privileged and materially comfortable people in the world. Colleges themselves have become part of, or at least complicit in (which is the same as being part of), the problem. Deresiewicz has detailed this line of commentary so many times better than I ever will.

But, aside from colleges and capitalism, tonight I indict the overachiever debate itself -- the discourse maintaining the sellout conundrum as a conundrum -- in its 2019 Rona Wang form, in the present 2021 time -- as being part of the problem.

Deresiewicz advocates for the dismantling of elite educational institutions altogether, and for their replacement by freely accessible, publicly-funded top universities -- "democracy" after "aristocracy" and "meritocracy." But to the "young people who have written to ask...[how] to avoid becoming an out-of-touch, entitled little shit", Deresiewicz writes that he "[doesn't] have a satisfying answer, short of telling them to transfer to a public university."

In this non-answer, Deresiewicz affirms Wang's archetypical overachiever's conundrum: you went to an elite school, and now you're too good to do good. And in doing so, he strengthens in student readers the very hegemony he seeks to dismantle. HYPSM institutions and students mask the lengthening of the gap between them and everyone else with a rhetoric of their own fundamental flaws, and avoid any concrete responsible action by appealing to their own inability to do so. The Andovers and MITs and Harvards of the world continue to churn out geniuses who think that their only possibilities for life are to either sell out to corporate nothingness or wallow in your own inability to matter -- a dichotomy from which it's not so difficult to arrive at as absurd (if you'll forgive my unnuanced and context-less judgement) of a stance as "billionares' actions are far more influential than grassroots efforts," as a Stanford friend once said.

This has been a thoroughly negative commentary so far, but the passion to make it came instead from a deeply hopeful belief of mine -- the underachiever's solution to the sellout's conundrum, if you will.

I spent my gap year talking with techies and dropouts about how useless school is. I spent it trying to leapfrog elite schools in their elitism and harness the power of capitalism directly to elevate myself and other others. I loathed what I was doing enough to apply to and enroll at a liberal arts school to become "a mindful citizen of the world, to do things with purpose", as Wang put it, but I soon was struck by the same fatalistic outlook as Wang's overachiever and Deresiewicz's "out-of-touch, entitled little shit." Confronted by the conundrum of all my friends being pre-law or pre-SWE or pre-whatever and my threatening to be the same vs. the absolutely dismal outlook of the academic literature I consumed detailing how racial, gender, and class oppression will everywhere and always find a way to assert itself and all resistance seemed futile, I wondered if there was any achievable meaning in this life.

Several nights I wrote things along these lines in my sporadic journal, sometimes when I was ahead on schoolwork and feeling empty, sometimes when I was procrastinating schoolwork and feeling stressed.

One night I questioned what I did enjoy, and I wrote about making software, making music, spending time with people. "Maybe life is as simple as just pursuing these," I wrote. "I can't conceptualize a happy life outside of this 'hedonistic treadmill': larger purposes seem like only transitional forms, and overindexing them crushes the joy that does exist in life. Running on a treadmill could prepare you for a marathon, but there's no reason to over-glaromize the marathon and dismiss all else: all should be driven by a love for running in the first place."

This isn't to dismiss larger values and missions, only to assert that centering momentary joy and de-centering self-serving dichotomies of meaninglessness must be a part of their pursuit rather than antithetical to it. Palestinian poet and activist Mohammed El-Kurd: "I get most inspired by [my family] because they are faced with such detrimental challenges to say the least and they are able to face those challenges with satire, with laughter. Laughter is the thing that has most often inspired me these past few years.”

The sellout's conundrum debate is valuable only if its a transitional stage to something more: to students practicing resistance to the conundrum dichotomy after they are made to recognize it, to the harnessing of intellectual ambition for concrete action rather than abstract stupor.