I made a reading list. If you want to be good at thinking and know much about the world, these are the best books to read by the best thinkers. In particular, if you don't understand Ayn Rand and Karl Popper then you're at a huge disadvantage throughout life. (Almost everyone is at this huge disadvantage. It's a sad state of affairs. You don't have to be, though.) I put lots of effort into selecting the best books and chapters to highlight, and including brief summaries. The selected chapters are especially important for Karl Popper, who I don't think you should read cover-to-cover.
Many other philosophy books, including common recommendations, are actually so bad that people think intellectual books suck and give up on learning. So I want to help point people in the right direction. (If you think my recommendations are bad, speak up and state your judgement and criticisms. Don't silently dismiss the ideas with no possibility of being corrected if you're mistaken.)
Ayn Rand is the best moral philosopher. That covers issues like how to be happy, what is a good life, and how to make decisions. There's no avoiding those issues in your life. Your choice is whether to read the best ideas on the topic or muddle through life with some contradictions you picked up from your culture and never critically considered.
Karl Popper is the best philosopher of knowledge. That covers issues like how to learn, how to come up with solutions to problems (solutions are a type of knowledge, and problem solving is a type of learning), and how to evaluate ideas as good, bad, true or false. Critical thinking skills like this are part of everyone's life. Your choice is whether to use half-remembered half-false critical thinking skills you picked up in school, or to learn from the best humanity has ever had and consciously think things through.
I made a free video presentation covering the reading list. It'll help you understand the authors, find out which books interest you, and read more effectively. Take a look at the reading list, then check out my video overview.
Watch: Elliot presents the reading list. (This video is also a good introduction to philosophy and Fallible Ideas.)
If you have some interest in learning about reason, morality, liberalism, etc, please take a look at the reading list and watch the video. This was a big project to create a helpful resource and I highly recommend at least looking it over.
I also recorded two 3-hour discussions. I talked with other philosophers who are familiar with the material. We talk about what the books say and how they're valuable, who the authors are and what they think, why people have trouble reading, and some philosophical issues and tangents which come up.
If you love reading books, dive right in! But if you're like most people, you'll find podcasts easier. Most people find verbal discussion more fun and engaging than books. The podcasts will help you get information about what the books are like, which can help you become interested in the first place.