I've read that guide before, I just thought it was too much for what I want. After some thought, I guess my main interest is mostly towards critical theorists, some contemporary existentialists like Sartre, and other "outward" philosophers like maybe Macintyre. I've always been fascinated by them, through my professors, through my adjacence to the left, to the thoughts and literature of existentialists. I've read Society of the Spectacle and I wanted more of that, but of course I've read sort of other "philosophical primers". I don't expect myself to be a philosopher, but I want to delve into the ideas of the people I'm interested in headfirst. I know it sounds arrogant, but I believe that I'll read and study Nietszche, Heidegger, Kant, and even Hegel once I'm done fully indulging myself with their successors, and once I believe the best way to understand contemporary philosophies is to delve deep in the past.
So far, my arrogant "curriculum" looks like this: Reading Plato (am doing this right now, I actually expect to be finished reading in two months, since I'm pretty disciplined, and I think I'm capable of comprehension) Another two months of Aristotle's foundational work. Then I wanna read the liberal/enlightenment era philosophers, Hume, Rousseau, Locke, Hobbes, etc and a bit of Frege since I'm a STEM student. For some reason I expect it last two months still. Then I'll brush up on the history of German idealism and French philosophy in the books listed in this thread, and finally modern critical theorists, post-Marxists, existentialists, the whole shebang. This one has no time limit, since I'm pretty much reading for "leisure" now. If it ever takes longer than that, I'll adapt my timeframe, but whatever happens next, like studying Hegel or Nietszche himself for example, is dependent on what I learn or wish to learn after reading such works
So basically, the question on "What do i have to lose?" is not about the value of the knowledge itself, but rather the impact of me skipping in depth studies of past work. Thanks for the input though, I hope this post also gets a reply.