I have always worked for myself and very much have a portfolio career. It's what I know and it is what I love- especially now I have a family as I can be flexible and combine my career and home life.
I know many who take the traditional career route that is encouraged by schools. You know the drill; get good grades, pick a respectable college, go to a reputable uni and do well so you can land a secure, high earning job. However when these expectations are shared, there is often an emphasis on what you 'should' do rather than what maybe makes you happy. I'm sure we have all found ourselves simply 'go through life' and not really thinking about whether this is what we want or not...well until we have that moment at 2am/after a few wines/