Interesting that you seem to be like me in wanting people to find their own path instead of influencing them in one direction too much. My meta is that this gives them more ownership over their chosen path, from which they'll potentially derive more pleasure and more meaning :)
Trying hard to have people make up their own mind can be hard for dating, though.
I can't tell you where you could/should start, because I feel like I would already influence you too much by taking some sort of choice away from you.
I will link a few essays I could find that are available for free and are not too long. I'm already influencing you a little bit by making this selection, but I urge you to do your own research: If you like one of the stories, try to find out who was influenced by whom (e.g. Kafka doesn't directly address meaning but influenced Camus; Nietzsche was influenced by Schopenhauer), and consider reading things challenging the author.
[1] The Last Question - Isaac Asimov (http://www.physics.princeton.edu/ph115/LQ.pdf)
[2] Metamorphosis - Franz Kafka (http://www.gutenberg.org/ebooks/5200)
[3] A Clean, Well-Lighted Place - Ernest Hemingway (http://www.url-der.org/a_clean_well_lighted_place.pdf)
[4] On Truth and Lies in an Extra-Moral Sense - Friedrich Nietzsche (http://www.jpcatholic.com/NCUpdf/Nietzsche.pdf)
I've often see people link the Stanford Encyclopedia of Philosophy, so I'm gonna do it as well: http://plato.stanford.edu/index.html
While I'm writing this gutenberg.org seems to have some problems, but just search for "Metamorphosis Kafka", and you should find plenty of other sources.