Ask HN: How did you get from A - B?

As I seriously consider a change in career I find myself wondering, how windy is everyone else's path? I know I'm not alone here, I started off (in college) striving to be a starving writer, moved on to CS when I realized I liked eating, then (after a semester of machine language) came Mech. Engineering. Now, after graduating I find myself heavily involved in the financial sector, and I've begun planning on working my way into a start-up/younger company in the Bay.

How many hats has everyone worn? What were they? When changing roles what have people done to gain traction? (both in finding work as well as developing the needed skill set if it was absent before)

Just curious for curiosity sake.

edit : cleaned up a sentence that was bothering me