An intellectual starter kit

Being an intellectual isn't all navel-gazing, it's the necessary foundation to being able to properly communicate and wrestle with your own ideas. It's something that provides the underlying structure and skillset necessary to be a good thinker and good communicator, both of which will serve you well in your career and your relationships. It is not, as some other commenter put it, "to make yourself feel smart".

I am frankly a bit shocked to find anti-intellectualism to abound on Hacker News of all places. The core of intellectualism is curiosity, the same driving force behind the hacker spirit, and intellectualism at its base is closely aligned to the hacker ethos.

What works best, I think, is to go with what deeply interests you while periodically challenging yourself with things that are out of your comfort zone. This way you can start anywhere - in my case it was Harry Potter, but it can be anything else: LOTR, Stephen King, anything. A possible progression would look smth like: Harry Potter -> the Hobbit -> LOTR -> A Song of Ice and Fire etc. Each step is a bit more challenging than the previous. Once you get to ASOIAF the world is your oyster: you can focus on history, sociology etc.

Always challenge yourself, always approach things critically, always pursue things that spark your curiosity, not some static list of "great books". With enough time you'll get to some of the great books anyway, but you'll do it in a way that makes sense for you.

Also, use books as tools, make notes, fold pages etc. Buy cheap paperbacks, use them, re-use them. Become a professional learner, not a coffee-table "intellectual" full of other people's pre-digested ideas.