I recommend trying to familiarize yourself with the main fields in philosophy first (aesthetics, ethics, postmodernism, whatever) and major contributors. I did this mostly through podcasts. Pick a few philosophers from you favorite field and try to read some of their smallest essays. There's usually an online copy floating around and then flesh out your understanding against secondary sources (reviews, response, wikis or podcasts discussing the piece, etc). Eventually you can work your way up to bigger game, but that's how I do it as an amateur with a passing interest