That's an interesting question Zeeno. I believe in the age old adage ... change is the only constant. We are always in flux even if it is not a concious decision.
However you are asking about making that decision to change and I guess feedback, self evaluation and reflection are some tools to look at yourself and your life and help yuou with that decision. We do it constantly with our work in our annual reviews, performance evaluaitons and project feedbacks, lesson learned, etc... we should apply those to our lives as well I guess.
I dont knwo if I've answered your question... I have a lot more to say so let me know what you think and we can keep the dailogue going...