The intriguing topic of whether people should work for the same organisation in the entire working life or rather creating some variations and opportunities throughout their career has sparkled a debate where people in society are mired in this controversy about their ensuing careers. From my perspective, in this dynamic world, both ways have their own uniqueness to assist an individual on their own path to success, but as a long term strategy, choosing to work for different organisations could be the better option. In order to draw an analogy to scrutinize the bone of contention, a holistic analysis will be established on both sides of the spectrum before making a conclusion.