There is so much I have to learn about everything! … Any leads on where to start? Do I start with logic, or politics? History or economics? Personally, I know myself best and I think that what I need is something more related to the individual, in terms of books that discuss values and such a la Virtue of Selfishness. Any suggestions.
There are different ways to answer your question, so here goes:
It’s hard to answer your question as stated, because there are simply so many good books out there. If you are looking to put together a reading list, you need to specify your goals and values. The more specific you can get, the easier it will be to answer this question. If what you have in your mind at the moment is something along the lines of “I need to learn as much as possible about everything”, you’ve set yourself up to fail, because nobody - including Ayn Rand - can master every topic under the sun.
That said, a general education across a range of subjects - arts, sciences, humanities - is a wonderful thing. It can provide an overview of the fundamentals of different fields. For someone about to enter college, that can also allow one to explore alternatives if one’s career goals are not yet clear.
14 years after reading Ayn Rand for the first time, I still am discovering new authors such as novelist Rafael Sabatini (Captain Blood, The Sea Hawk) and military historian / classics professor Victor Davis Hanson. I haven’t set out a reading list, but rather have done what Gail Wynand did: took up one book after another in what might seem to someone else a random path. Often I would discover something in one book that perked up my interest and led to another book that I didn’t anticipate. Cliche it may be, but learning really is a life-long process.
Over the years, a secondary Objectivist reading list of sorts has developed. By that I mean books Ayn Rand or Leonard Peikoff have recommended in their writings or lectures, as well as excellent materials in fields often of interest to Objectivists (such as economics or architecture). Some used to be available through the Ayn Rand Bookstore; some are still for sale at The Paper Tiger. You might look through the bibliographies or book reviews in the Objectivist literature as a starting point. These books are among those that Objectivists often read, but nobody, to my knowledge, has read them all.
The best answer to your question: follow your passions. There is no one “correct” way to learn about the world, in terms of starting with a particular field over another. If you want to learn more about egoism or individualism, as you indicate, be aware that very few philosophers even attempted a defense of them; nearly all were altruists. The exceptions were Aristotle, Nietzsche and Spinoza, despite their errors. (I believe I learned this from Peikoff, but my memory is fuzzy on this.)
If you’re interested in philosophy as such (vs. applications), learning the contrasts between Ayn Rand’s views and those of these guys would be quite instructive – and not a small undertaking. One of my favorite philosophy courses was a 10-week class on Aristotle’s ethics.
So if you can be more specific, there are plenty of authors to be recommended. Bear in mind that there’s only one Ayn Rand - someone who was revolutionary across so many fields. I would say the closest person in that regard would be Aristotle.