Hackers are creating knowledge and sharing information since the inception of technologies. They do have a deep understand on the inner workings of systems and different motivations. Just like a company that faces competition and external challenges, and tries to build their products to face those challenges, improving at each generation (or not), a hacker builds up knowledge and evolves based on that. Given different objectives and targets, they will focus their abilities in separate areas. If a hack seems easy to someone, maybe it is because he already built the knowledge, understood the challenges, but that does not mean somebody else is not in the process of doing so, or that this other person does not have fun while doing it (and thus, really does not care about the real complexity). Different objectives, different measures. And it is possible to have fun, do interesting (and challenging) things while having the usual benefits of a work: in different ways (and each individual needs to understand that, take responsibility for their own decisions and pay the prices for the wrong ones as well). Either in a technical career inside a big corporation, or as an individual collecting bounties (two apparent extremes that share lots of common factors), a researcher needs to makes conscious decisions, which we hope will be discussed in this talk. In the end, the objective is to demonstrate that challenges exist, opportunities as well, and that it is possible to have different ways in life keeping the same fundamentally technical priorities: build knowledge and have fun.