When I graduated from Harvard, it never occurred to me that eight years (and one Masters degree from Yale) later, I’d be desperately trying—throat tightening, palms sweating, will to live shrinking—to solve a tough question on the SAT. Even worse, I was expected to know the answer; I was the SAT tutor, after all. My student, whose parents were paying two hundred and fifty dollars an hour for my services, stared at me expectantly. There was only one thing to do: Smile mysteriously, assign the problem as “extra credit homework,” go home, and check the back of the book.

The deeper question that was gnawed at me was both simpler and more intractable: What in the world was I doing? I had degrees from Harvard and Yale (okay, they were in English and Acting, but still) and here I was supplementing my totally rational plan to become a massive star of stage and screen by working for an elite New York tutoring company, employed by wealthy parents, hoping to give their child an edge. (As a friend said, “They’re rich and desperate. Make the most of it!”)

After I raised my students’ SAT scores, I was expected to help with their college applications, coaching them on topics for personal statements (Golf? My cat? The color green?) and then meticulously editing their essays into something presentable. When I told a worried parent that I would be happy to provide young Johnny with essay “suggestions,” she looked at me, brows knit: “Honestly, I think Johnny needs more than just suggestions. He needs someone to sit there with him and get the words out. Not write it for him, of course.” Oh no, of course not.

I felt torn. On the one hand, after you’ve spent four hours with a recalcitrant high school senior, quizzing him in the hope of finding something—anything—that you can use as the basis for his personal statement, you pretty much hate him. On the other, I felt great sympathy for my students. I’m sure a handful of next year’s Harvard freshman class split the atom in pre-kindergarten, but for most of us, the prospect of summing up who we are with one brilliantly crafted piece of prose is daunting, to say the least.

I myself shuddered at the thought. But then again, I was living in my parents’ basement and stealing their food and toilet paper. So I began to care obsessively about my students’ applications, staying up late proofreading attempts to perfectly describe “When I lived in Brazil,” or “The Museum Trip That Changed My Life.” Before long I found myself switching out vocabulary words to make the prose more impressive, cleaning up a paragraph, suggesting a new ending, or even restructuring the entire essay.

Admissions committees are—or should be—well aware of the leg up that rich kids have in the application process. But the more I coached and tutored, the more I wondered whether the so-called advantages I was providing might actually be hurting more than helping. Was it really an advantage to spend Saturdays drilling test taking strategies that (unless you become an SAT tutor) have pretty much zero relevance to your future life? And what would it feel like to be admitted to the college of your dreams on the basis of an application that had been managed, tweaked and supervised by somebody else?

Perhaps no amount of tutoring can make up for the feeling of not having truly earned one’s admission. “Gaming the system” sounds a lot like a euphemism for cheating, and too much coddling and coaching may do irrevocable damage to a young person’s budding sense of integrity. Now I see that the most valuable gift I could have given my students would have been to let them succeed or fail on their own terms, maybe even learning that what seems like failure can be success in disguise.

As I wrestled with my own feelings of failure—Harvard grad turned mediocre tutor and night-time toilet paper bandit—I began, slowly, to write about it. “Johnny’s” mom’s words, along with those of other parents and students, slowly worked their way into scenes, and ultimately became my first full-length play, IN, which tells the story of a high school senior and his mother, who is desperate that he get into Harvard.

They hire a tutor, Sara, a slightly lost and miserable Harvard grad (where did I get that idea?), who learns over the course of the play to mistrust simplistic visions of success and failure, ultimately finding the strength to stand up for what’s true. Writing that play led to my first playwriting agent, and then more plays, screenplays and television work—and suddenly I had a career as a writer. I am proud to report that it’s been a very long time since I stole a roll of toilet paper and, while I still am stumped by problems all the time, none of them are from the SAT.

Bess Wohl '96 is a writer and actor, working in theater, film and television.  She divides her time in between New York and LA.