Before people start jumping on Mr. Rad and getting hung up on whether or not you should freelance first, work at a startup, big company, etc, I want to make a meta-comment. Too often I see high expectations from posts like these or biographies or whatever. Like Charlie Munger recommends to study Benjamin Franklin's life, so people read Franklin's auto-biography expecting some magical key to making their life memorabl…
I love this advice. I've consumed tons of people's stories and each person took a different path. When you first start consuming this kind of stuff and noticing that, you get a little miffed, but later you come to the realization dharmon articulates here: there are tons of ways to make it work.
Make a mental note of the advice you like and try it when appropriate. Mix and match to find the cocktail that works best for you. My path is not the canonical one, but it is a path that has worked at least one time. ;-)