It might sound a bit silly, but I've always wondered, if I was a 'successful' musician, in a band, how I'd prefer my career to span.
Like, would you rather be in a really decent underground indie band that builds up a big following, and is the kind of... in band, but only lasts for two or three records (like the NME people now, not the super big ones, but Klaxons or something). I mean, you'd have lots of credit, and you'd be able to fill medium sized venues.
OR, would you rather be in a band who's music isn't very 'buzzing' or current, but has a 10 year or more career and end up being pretty rich. Like Coldplay maybe? You still do what you enjoy, but to a lesser extent. Play up to the record company's wishes more, than being able to be experimental and doing what you like.
My comparisons are really shit, I know, but I think you get the idea of what I'm saying.