Gangsters, Drag Queens & Hookers

A story: a few years ago I had a client. He was a good client, as almost all of my clients are. Nice guy. Strong test scores. Not an outstanding career history, but he showed solid advancement at his company and, more importantly, he showed a willingness to go beyond his basic job duties and the necessary skills to succeed in those endeavors.

The only problem was that he didn't have much of a personal life. He had few hobbies, but that didn't matter anyways since he had no free time. His career was his life. In fact, he was so focused on his career that when it came time to write a "personal essay" (e.g., Describe how your background, values, academics, activities and/or leadership skills will enhance the experience of other Kellogg students.) he insisted on describing how he had worked nine different part-time jobs in college to prepare himself for his job. For my client, the most important thing for the adcom to know was the number of jobs he worked. From an admissions perspective, such career focus is clearly admirable, but not if it requires sacrificing a well-balanced life. I told him to try it his way first and see what happened.
We went back and forth over a few drafts that he wrote, each one quite boring in my opinion because he was in essence discussing his career, which had been covered already in several other essays. Finally I asked him, "Which of those nine jobs was the most interesting?" He paused. Looked down. Thought quietly for a moment. Then he said brightly, "There was the time I worked at a gay bar."
Well. After that, he proceeded to tell me one of the best MBA stories I've ever heard. He worked as a bar back at a pub in a seedy part of town. The clientele consisted of off-duty prostitutes, gangsters, and gamblers. The owner was a drag queen. He became friends with them all and had a great experience. Now, my client went to a very conservative college and worked at a very conservative company, and on the surface, was quite conservative himself. He said his friends and parents thought he was crazy for working there, but the experience opened his eyes to a new world and introduced him to people he would have never met otherwise. He said he had been enriched by the experience.
This was the story he needed for many reasons. It provided balance to his essay set and showed a surprising and positive side to his personality. It showed a willingness to take a risk and do something unexpected that the people around him didn't approve of. It showed he was open to serving and working with people that were very different from him. In some ways it was a small story, but it had big messages. (Most applicants have these stories if you know where to look.)
I used these reasons to convince my client to write about his experience. He agreed to try, and his next draft was almost perfect. This essay became his favorite and he insisted on sending it to every school, either as a main or an optional essay. In the end, he received invitations from almost every school he applied to, and while I cannot say with 100% certainty that his personal essay was the main reason for this success, I can say with great confidence that the essay made a positive and lasting impression on the adcom and that it played an important factor in receiving so many invitations. I worked with this client several years ago, and I can still remember the details of his story. These are the kinds of stories you want to include in your application packages.
This story for me also illustrates several important things that I often tell my clients:
1) Balance among your essays is crucial.
2) You can write about almost anything in your essays if you handle it properly. Indeed, some of the most memorable essays I've read came from "small" stories.
3) Taking a chance in your essays by telling an unusual story can pay big dividends, especially if you have nothing to lose.