You're not thinking about the longterm consequences of this. Once it's posted it on the internet, it's out for the world to see - FOREVER. Even if the essay is anonymous, it wouldn't be difficult to figure who wrote it based on the activities and leadership roles that might be mentioned in the essay. What you wrote on the essay could come back to haunt you. I mean, imagine if your patients, colleagues, and spouse could read what you wrote years ago. Not only that, but the residency director and attending physicians might read it for kicks - which would be bad because these types of essays tend to sound naively childish.
And then there's always the liability issue. What if you were involved in a malpractice suit and the lawyers dig through your file and discover that you mentioned a DUI charge in your essay? What if you decide to run for office one day or get appointed by the president or Congress? Don't think for a minute that the media and the public won't put your essay under the microscope. They will find out about any involvement that you had in college with any controversial, idealogical groups (pro-abortion, socialized medicine, etc) and these things might hamper your chances of being elected or appointed for whatever job it is you're looking for.