Majority of the time, this phrase is used with a negative connotation. Gaming the system has nothing negative about it. In fact, it is a way of life when you are part of a society. And in this ultra-connectedness era, nobody can claim to be living a life of their own, totally unaffected by what is going on around her. We are all integral to the system(s) that exists.

We are always looking to understand what needs to be done in order to achieve something, be it studying for an exam, preparing a resume, buying a new car, getting a promotion, securing admission for children in good schools, or anything else. We identify what needs to be done and then we go about getting that done. This is plain and simply, gaming the system.

Marketing is where this is most apparent. There are standard practices for gaming the system here. It is part of the job description to understand what it takes to sell something to a potential customer, be it offering a discount or changing the product features altogether, and then get that done to make the sale.

Gaming the system is inevitable. Everybody ends up doing it. But it is up to you to decide how often you wish to do it. With short-term goals, you will end up gaming the system for every new goal that you set yourself. This will be so frequent that you will not build a coherent profile of yourself (or your brand). This will progressively make it harder for you to game the system because every time you identify what needs to be done, you will find a growing list of things to be undone (things that you did to achieve your previous short term goals).

Gaming the system is inevitable. But do it with a set of longer term goals in mind. Or you will live a life where you're constantly putting out fires.