Why Every College Essays Begins, ‘The first time I . . .’ — And Why They Shouldn’t

If you’re interviewing doctors, do you want to know about a surgeon’s first operation, or about the surgeries they performed last year? If you’re a coach holding tryouts, do you want to know the first time a player made a basket or their points per game last season? If a business is hiring, do they want to hear about the lemonade stand at age 8 or the internship last summer? If you’re a guest at a dinner party, do you want to taste the host’s “first” attempt at a recipe?

If you’re choosing a college counselor, do you care where their “first” student got into college?

The answers should be obvious. And they should be just as obvious for college applicants as for all these other types of people.

Oddly, though, on college essays, students almost invariably begin with the phrase the first time that … I see it constantly — on essays about studying science, about debate, about playing soccer, about doing community service, about almost anything a high schooler might have pursued for more than 30 seconds.

I understand the instinct. When you’re telling a story, the easiest way to start is at the beginning. Students naturally go to what they consider the “beginning” to be. They may want to capture a longstanding pursuit, or tell a childhood story that their parents think is cute. Or, they may be eager to demonstrate the ever-popular theme of personal growth. And the farther back you go, presumably, the more growth you can show.

(Nearly as common is the “first time’s” close cousin, I have always . . . as if the student built robots or wrote poetry in the bassinet.)

“First times,” though, are achingly predictable. They usually involve apprehension, difficulty, ignorance, and clumsiness. Nobody is good at anything the first time they try it, and nobody understands what they’re doing the first time they do something. With all due respect to Foreigner, the “first” time is often the worst time.

One of the privileges of telling one’s own story is that the writer gets to define the terms. You get to decide what to keep and what to leave out. You get to decide where to end and where to begin. When applicants spend words talking about first times, they waste words, space, and the reader’s attention on mostly irrelevant details from the distant past, rather than presenting compelling details that reflect who they are and what they can do today.

If a student absolutely must refer to a first time — say, for dramatic effect or because they can’t part with the story — they shouldn’t put it at the beginning. There’s a time-honored literary and journalist tradition, in medias res, in which you start a story in the middle, then fill in the background later. Almost every newspaper article follows this approach, to an extent; many nonfiction books do too. Done well, that can be far more effective than the predictable “first time” story.

Rather than lean on the simplistic objectivity of a “first,” consider instead more nuanced — but far more compelling — possibilities:

• Best
• Favorite
• Most recent
• Most mature
• Most sophisticated
• Most challenging
•Most amusing
• Most emotional
• Most collaborative
• Most revelatory
• Most educational
• Most surprising
• Most rewarding

(Or, dispense with superlatives altogether. Don’t force yourself to come up with “mosts” and, instead, just pick something you’re reasonably excited about.)

All of these approaches can yield great stories and ideas without going back to the beginning of time.

It’s also useful to contrast college essays with other forms of writing. When we read biographies  —  whether written by an outside author or as an autobiography — we want to see what the eminent personage was like in some larval, inchoate stage. But the features that are fascinating in a biography are very different from what’s relevant in a college essay. Biographies are about people who have lived full lives, had compelling experiences, or achieved fame. We typically read biographies because we are already interested in and, often, impressed by the subject.

College essays are about anonymous teenagers. Readers are not going to treat them with the same reverence.

The fixation on first times feeds into what I call the fallacy of longevity. This is the assumption that doing something for a long time is inherently admirable — that it shows loyalty, consistency, dedication, competence, or the ever-popular “resilience and grit.” But none of those things is necessarily true. You can do something for years and remain incompetent. I’ve surfed for decades and have never caught a wave bigger than two feet. There’s nothing wrong with that — but I’m not about to try out for the Pepperdine surf team.

Plenty of people do things out of habit, or because their parents made them, or because they haven’t yet been exposed to other options. Longevity doesn’t necessarily mean anything. It could signify dedication, expertise, and, to cite a cliche, “resilience.” But it could also signify stagnation, hesitancy, or lack of imagination.

Conversely, the longevity fallacy ignores the profound power of new interests and new inspirations.

Life is a process of discovery — especially in high school. Very often, that spark of discovery leads to greater effort, growth, and competence than anything pursued by rote or habit. Plenty of people discover new interests late in life that turn out to be profound. People discover new academic interests, careers, fashion styles, hobbies, art forms, places, preferences, lifestyles, political convictions, and even religions at all stages of life. Sometimes, those late discoveries lead to greater success, enjoyment, and conviction than any of their earlier pursuits did. These discoveries can take place in adulthood, college, and, yes, even high school. (My favorite class in college was in the second semester of senior year.)

As for my first student: I don’t remember who that was, and I’m sure they don’t remember me. The 2000s were a long time ago. Whoever it was, and whatever they wrote on their applications, I hope they’ve had plenty of great discoveries and plenty of new stories worth telling since then.