I was just reading this Hegel book I'm trying to (finally) understand, five minutes ago, and only in the last day or so have I really felt like I have a grasp on Hegel, for the first time in years. I always knew tidbits about him or about how he was employed by others, but I never really GOT Hegel, and I knew nobody else does either. So this is my first interaction with a contemporary, would-be authoritative attempt at "What Hegel Actually Meant," and it's been brutally, mind-breakingly difficult to understand.
But I finally had the breakthrough (where your mind finally goes "ohhhhhhh, that's what all of this means" and it all clicks into place) like yesterday, so I was thinking: How would I have advised myself to do this years ago, when I was just learning who Hegel was and I obviously would have appreciated having such an understanding?
I tried to think of the pros and cons of various approaches, but in the end every approach came down to this basic maxim: "Just keep reading, and you'll get it eventually." I wouldn't have understood this shit if it hadn't been for a very vague and nebulous skillset in a hundred other areas of philosophy, that I've gained by haphazardly reading my way through the discipline. Bad books can be as useful as good books, if you read them right. Mistaken interpretations provide the ground for correct ones, later on. The answer really is always just: Keep fucking reading.
I think the only thing college did for me was force me to do this, to keep reading, and to keep reading lots of things rather than becoming provincialised. As long as you're serious, and you make a life's work out of being an autodidact, there's literally no reason you can't do it.
In fact, if you really pull it off you'll be way better off than most college kids, because most of them read the bare minimum skeletal framework of talking points required to pass exams, and don't contextualise anything. They never reach those critical mass moments when islands of knowledge crash into each other and you realise you've been limning a greater whole all along. Even grad students mostly "keep reading" only until they get to grad school, and then ultra-specialise in something incredibly narrow.
So yeah, just keep reading broadly, widely, keep relating it, and always take it seriously. Don't think of it in bourgeois ways, like "I want to be better-read so I can show off at parties."