Before I started writing my essays, I created a list of accomplishments and experiences that I thought would make good material. I thought I could show good career progress, continual escalation of responsibility, and great initiative. But as soon as I started putting it to paper, I would get discouraged -- nothing I wrote seemed good enough for the top business schools, especially in comparison to the sample essays in the back of my how-to-get-into-b-school book.
One of the sample essays in this book was written by a guy who, in his early twenties, had moved to South America, taken over a fastener company, completely automated their supply chain and inventorying systems, renegotiated their supplier contracts, dealt with unions and corrupt government officials, grew the company by leaps and bounds, and ultimately sold it for a big profit - all before the age of 30. I was managing a $500K project at the age of 30. Seemed a little underwhelming.
In retrospect, I'm not sure how useful those sample essays were. They were discouraging, and they didn't tell me much about how to write a strong essay. When you've turned around and sold a South American fastener company before the age of 30, you don't need to be a very good essayist to give a compelling answer to the question, "What are your three most substantial accomplishments and why do you view them as such?" But when you've spent 8 years as an engineer for a tech company and you're applying to a top school, you're going to have to put some work into it.
I re-wrote my "career progress" essay several times before realizing that the problem wasn't the organization of my essay or my writing style. The problem was that I kept comparing myself to the South American Fastener Turnaround Guy. There was nothing I could do to make my past experiences compare with his; all I could do now was focus on casting my experiences in the best light.
As I read my career progress essay now, it doesn't seem as boring as it did at the time. When you've been working on the same essay for tens of hours, it's going to seem a lot more boring to you than anyone else. But still, none of my essays are exactly Pulitzer material. They flow well, address the essay topics directly, and convey my talents and interests - but they don't magically transform me into some kind of business superhero.
I think one reason why the b-school essay writing process is so difficult for people is they have impossible expectations of their essays, much as I did. It's true that you need to be able to demonstrate career progress, management aptitude, people skills and the rest of it to get into a top school. But even the top business schools aren't filled with South American Fastener Company Turnaround Guys - there may be a few of those people, but the rest are mere mortals like you and me.