As I started reading through Phillip Lopate's introduction to his anthology The Art of the Personal Essay, I expected to find the usual pages I have to flip through to get to the good stuff. Instead, I found a great description of the personal essay. As you try to figure out whether your essay is on the right track, here are 7 questions - adapted from Mr. Lopate's introduction - you can ask yourself about your essay:

  1. Is It Conversational? "The hallmark of the personal essay is its intimacy. The writer seems to be speaking directly into your ear, confiding everything from gossip to wisdom."
  2. Is It Candid? "'We must remove the mask,' says Montaigne."
  3. Is It Vulnerable? "Part of our trust in good personal essayists issues, paradoxically, from their exposure of their own betrayals, uncertainties, and self-mistrust."
  4. Is It Self-Questioning? "Personal essayists are adept at interrogating their own ignorance. Just as often as they tell us what they know, they ask at the beginning of an exploration of a problem what it is that they don't know - and why."
  5. Is It Provocative? ""It is often the case that personal essayists intentionally go against the grain of popular opinion. They raise the ante, as it were, making it more difficult for the reader to identify frictionlessly with the writer."
  6. Is It Self-Contradictory?. "The novice essayist often errs by taking a strong moralistic stand and running it into the ground, with nowhere to go after two paragraphs. Here the personal essayist will open up a new flank, locating a tension between two valid, opposing goals, or a partial virtue in some apparent ill, or an ambivalence in his own belief system."
  7. Is It Uncertain? "To essay is to attempt, to test, to make a run at something without knowing whether you are going to succeed." Also: "There is something heroic in the essayist's gesture of striking out toward the unknown, not only without a map but without certainty that there is anything worthy to be found."

Write to Discover

I write blog posts to chronicle my progress or, more frequently, lack thereof, in identifying the process that will take a student from "I don't know what to write" to "I just wrote my best essay." If you ask me, "What is that process?" I will tell you, "That's what I'm writing to figure out." I write to discover. You should do the same.

If you skim the questions above, you'll notice that they all hint at tentativeness. There is the sense of casting about for something. There is more doubt than certainty. There is something to be discovered.

Be a Spider

You just have to channel Whitman's poem A Noiseless Patient Spider. I tried to figure out how to sever a couple lines to illustrate the point, but I'm not that talented, and it's more fun to read all 10 lines anyway:

A noiseless patient spider, I mark'd where on a little promontory it stood isolated, Mark'd how to explore the vacant vast surrounding, It launch'd forth filament, filament, filament, out of itself, Ever unreeling them, ever tirelessly speeding them.

And you O my soul where you stand, Surrounded, detached, in measureless oceans of space, Ceaselessly musing, venturing, throwing, seeking the spheres to connect them, Till the bridge you will need be form'd, till the ductile anchor hold, Till the gossamer thread you fling catch somewhere, O my soul.

That sums it up. Explore. Launch your filaments until you connect. Onward, my spiders!

Poke at the Bugs

Every young child knows the excitement of overturning a rock, especially a big one he has to tug at to move. What will we find underneath? You might see worms, sowbugs, earwigs, and all other sorts of scurrying or wriggling unpleasantness. Once I saw a millipede. When that rock is overturned, you can do one of two things. You can put the rock back and pretend nothing's there. Or you can find a stick and poke at the bugs.

If your goal is to write your best personal essay, then you have to accept that you don't know what your honesty will reveal. And you have to resolve that whatever it reveals, you will examine, even if you don't want to. You're going to reconcile the person you are with the person you want to be. That's the self-questioning that leads to a good essay. That's what it means to poke at the bugs.

Good luck writing!


Jon Perkins holds a B.A. in English from Stanford University and a J.D. from Harvard Law School. He helps students with their college, law school, and medical school applications.