Ha ha ha! I know what you mean man! First of all, the specifics:
1. two pages = 2 sides
2. font size = size 10
Let me guess: Your essay has 1 1/2 pages of just career progress right? Even I was in the same boat. You happily finish listing out and explaining your career achievements and then realize that you went past the word limit 200 words ago. Trust me, the Kellogg essays have pretty liberal word limits. You should see the HBS essays....pure hell, I tell you.
To answer your question, I just painted broad strokes on my career progress to date. So I didn't really go into too much of the details. I guess there is really no other way around it. You write the first draft and then edit it and then re-edit it and then re-edit it....... (you get the picture right?!;)) till you are within the word limit.
Oh, and before I forget, you can shorten your sentences by just reorganizing them a little.
1. Use active voice as opposed to passive (e.g.
My company promoted me can be written as
I was promoted)
2. Use collective nouns wherever possible (e.g.
I was recognized for my efforts by my manager, VP and eventually my SVP can be written as
I was recognized for my efforts by senior management)
Hope that helped!