It depends on what you're looking for. If you're looking for Drescher style stuff then you're looking for a very specific type of contemporary, analytic philosophy. Straight off the top of my head: Daniel Dennett, Nick Bostrom and some stuff by David Chalmers as well as decision and game theory (good free introduction here).
If you're interested in contemporary, analytic philosophy generally then I can't really make suggestions because the list is too broad (what are your interests? Ethics? Aesthetics? Metaphysics? Epistemology? Logic?). Good general resources, however, definitely the Stanford Encyclopedia of Philosophy (which is a great resource), Philosophy Bro (for a lighthearted take), Philosophy Bites (for a podcast). The list here, cited by someone else, is a good guide to prominent papers some of which will be harder to understand without background knowledge than others.
If you have specific questions during your self-study, feel free to PM me and I'm happy to try and help (I'm far from an expert but also know substantially more philosophy than the average person).
Hello LessWrong,
I just (finally) finished Good and Real, by Gary Drescher. It was a very stimulating read, and I'd like to continue learning philosophy on my own. However, I'm running into a bootstrapping problem. I don't know what I don't know, and therefore, I don't know where I should get started. I've tried searching the LessWrong archive to see if anyone has made a post outlining a curriculum for someone looking to teach themselves the fundamentals of modern philosophy and logic, but either my Google-fu is weak or no such post exists. So, what should someone who is looking to reduce the inferential distance between themselves and modern philosophical thought read, and in what order?
Or, do you all think this is a quixotic quest that I should give up on?