Why College Applications Shouldn’t be “Fun”

Josh Stephens
6 min readOct 7, 2021
Probably more fun than final exams.

By Josh Stephens

A while back, the late, venerated David Foster Wallace warned his fellow Gen Xers about the indignity of taking a vacation cruise, which he declared “a supposedly fun thing I’ll never do again.” Emphasis on supposedly.

Wallace’s original essay, which inspired a book, is memorable because he’s undermining conventional wisdom. It’s understandable that bobbing around the ocean on a floating hotel with limitless buffets might, under certain circumstances, be enjoyable. Wallace tells us instead that a cruise is “an enormous primordial stew of death and decay.” So, there you go.

Sometimes the opposite situation arises — the insistence that something patently unpleasant is fun. In particular, what I find baffling is the assignation of “fun” to the process of applying to, daydreaming about, fretting over, and, most likely, getting rejected from highly selective colleges.

I admire highly selective colleges and understand why ambitious, elite students apply to them. I even appreciate the application process, if not for the decisions it elicits then at least for the self-reflection it inspires. I love supporting credible applicants to these schools, and I find the whole thing fulfilling, as I hope my students do. One thing I would never call it, though, is fun.

Apparently, some people disagree with me. Thousands of them.

The number of students who apply of highly selective colleges has been rising steadily since the beginning of time. Last year, partly because of pandemic-related test-optional policies, application numbers spiked like crazy — by 100% at some schools. Many of these applications were viable and earnest. Many were not.

Highly selective colleges can have such outsized reputations in adolescent lore that students often, regardless of qualifications, want to “take a shot” or apply seemingly for the sake of amusement. Last year, for instance, one of my students’ parents told me that her son applied to four well-regarded tech schools — and Harvard. She wrote, in the jauntiest terms, “the first four are for their CS, engineering, or technology specialties, and the last one was just for fun. :)” [emoji included].

I admire her sunny disposition. But I can’t imagine what’s so “fun” about near-certain rejection.

Absent an exceptional background, there is no honor in applying to an ultra-selective school only to add to the school’s body count. Applying to a highly selective college is not like buying a ticket to see if you win the raffle. It’s more like getting elective surgery to see if you have a tumor even though you have no symptoms. Applications often involve multiple supplemental essays, that all demand serious work. And that’s just the labor of the applications themselves, which can be negligible compared to the months of anticipation and anxiety that students endure before getting their decisions.

The odds are better at the casino. At some colleges, a full 95 percent of applicants lose their “bets.” While it’s true that applicant pools are so strong that some of the decisions are random, they are random within limits. The 50 percent of applicants whom Harvard rejects almost instantly are not random at all. They simply don’t meet the school’s minimum expectations. Among the strong applicants who remain — many of whom are strong for different reasons and fulfill different institutional priorities — decisions are unpredictable. That is, of course, the point of applying to multiple schools: everyone who takes the process seriously, evaluating themselves and their prospective schools soberly, will “win” in the end.

The college application process does not, by definition, reward students seeking instant gratification. There are no blinking lights. “Fat envelopes” don’t drop from the sky with balloons. The most successful applicants approach it deliberately, not impulsively.

The most immediate harm that comes from treating college applications like a game is that applicants focus on one “prize” at the expense of thinking deeply about all of their options. Even for students who promise not to get worked up about a long shot, it’s too easy to get excited about a school with a shiny №1 ranking. It’s harder to learn about less selective, less famous schools. And yet, when students put in that hard work and shake off the distractions, they almost invariably discover many schools that excite them.

Ideally, though, applicants shouldn’t focus on schools at all. They should focus on themselves.

There’s no doubt that the college application process involves a bit of self-promotion. If, yesterday, you tripped down the stairs in the morning and cured cancer in the evening, you’d probably want to tell colleges about your evening and let the morning slide. But, before applicants make fine decisions like these, they must first be honest with themselves. Promotion works only when it’s reasonable; otherwise, it’s basically lying. (Meanwhile, while we’re on the subject, the colleges’ promotional fervor is, let’s be honest, partially to blame for dashed hopes of tens of thousands of under-qualified applicants.)

Applicants who want to apply to selective colleges first must ask themselves whether they are, to use a fraught phrase, “Harvard material” (or “Texas A&M material,” or “UCLA material,” or “Georgetown material” or “get a job and start a career material” — or whatever). Here’s the thing: it’s difficult, and rare, to be a credible candidate to many schools. But “difficult” doesn’t have to mean “inscrutable.” Many different factors — including factors ranging from grades and test scores to life experiences and socioeconomic status — can contribute to an applicant’s appeal. And, of course, sometimes the most humble students, who think they don’t have a shot at all, are exactly the ones about whom colleges get excited. The key for students is to understand those factors and understand how they do or don’t apply.

Beyond the odds and predictions, a crucial component of asking yourself if you are “Harvard material” is that it’s OK not to be Harvard material. Billions of people get through life just fine without having gone to Harvard. Self-awareness, self-acceptance, and self-confidence are far more valuable than misplaced optimism is (and more valuable than a Harvard diploma, if you ask me).

Self-awareness means you can identify not only colleges that are realistic and right for you but also colleges that are wrong for you and unrealistic. It means spending time getting to know the colleges that seem most right and most realistic. It means that you can properly account for your strengths and weaknesses and, ideally, highlight the former on your applications. It means you can define your ambitions and come up with a reasonable plan for achieving them. Self-acceptance means that, once the application process is over, you can be satisfied and successful whether you get into your top choice, your “safety,” or anything in between.

And here’s what’s really cool: if students are honest with themselves and apply to appropriate colleges, then the application process can actually be fun. Rather than worry about an unrealistic reach school, they can get excited about well fitting schools and they can get even more excited about the varieties of self-discovery and self-expression that the application process entails.

Finally, a note for parents: Please don’t make your kids over-excited about a long shot college or feel badly about a less selective college. You have no control over the colleges’ decisions, and you never know where they might actually go. Don’t inflate a choice that is going to reject them instantly, and don’t undermine what might end up being their best choice.

Let’s be honest: college applications, while they can be exciting, entail plenty of drudgery. They are not fun. But they yield fun. That’s because almost every college you can imagine offers everything from classes and activities to football games and frat parties. Applicants will find fun, and much more, no matter where they go. And they’ll find the most fun when they’ve applied to schools that are suited for them and when they gain admission to schools that they’re excited about.

And, if ever they’re feeling down, they can at least be glad they’re on dry land, facing bright futures no matter where they go to college.

Josh Stephens is a veteran teacher and college counselor based in Los Angeles. He earned his bachelor’s degree in English at Princeton University and his Master of Public Policy at the Harvard University Kennedy School of Government. He can be reached at josh@joshrstephens.net.

Image courtesy of Stella Maris UK via Flickr.

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Josh Stephens

Josh Stephens is a veteran teacher and college counselor based in Los Angeles. Josh can be reached at josh@joshrstephens.net.