Philosophy is the name of the field which includes topics like: What is reason? How does reason work? How do I learn? How do I figure out which ideas are true or false? How to I argue and evaluate arguments? How do I seek the truth? (Those questions are from the sub-field of philosophy called “epistemology”. That’s the philosophy of knowledge, and it’s the most important area of philosophy.)
How do you learn philosophy?
When you disagree with something, or don’t understand something, or feel uncomfortable/hesitant/doubtful, stop reading and post to the Fallible Ideas Discussion Forum. Don’t gloss over problems; bring them up. Don’t pretend you’ll go back and discuss when you get to the end of the book; discuss now. You need to get issues addressed now so that you can take those answers into account while reading the rest. Mistakes will spiral out of control, and destroy the value of reading the rest, if unaddressed.
Mistakes are very common. When you read a philosophy book, you will form literally thousands of misunderstandings. This is unavoidable. However, most of them don’t have to last very long. If you think carefully enough about what you’re reading, as you go along, you can fix lots of mistakes. And if you discuss your thoughts, other people will point out more mistakes that you missed, and tell you ways of thinking about things that you hadn’t thought of, and give examples of their own thinking that you can learn from. Between your own efforts to identify and fix your mistakes, and the efforts of others you discuss with (who have different strengths and weaknesses than you, different blind spots, different knowledge), you can learn a lot without too many mistakes. But if you read a book passively, your understanding of the book will be so full of mistakes it will be pretty worthless.
Even with short pieces, like emails or blog posts, you should write your thoughts/replies/doubts as you go along. It’s typically best to write your comments/questions/criticism after each paragraph. If you’re concerned that your question/comment will already be addressed later in the text, you can write them now but only share them for discussion later. For the points that get addressed later, you can add followup comments on what you think the answer is, which is generally a better idea than dropping the issue. You’ll learn more by writing your thoughts out, even if they get addressed later, because it’ll help you figure out what you think and why. If you aren’t writing your thoughts, it’s because you aren’t thinking much, or your thoughts aren’t clear enough. If you have clear thoughts, they won’t be hard to put into English words. (If you’re really not used to writing, it will take some getting used to. Writing is a necessary skill if you want to be any kind of rational thinker, and writing will be enjoyable if you have a rational attitude towards it.)
If you want to learn much, it’s going to involve a lot of discussion. Even some of the world’s greatest thinkers – like Ayn Rand, who figured a lot out herself – valued discussion and benefitted from having a lot of discussions. And it’s much easier to benefit massively from discussion if you aren’t already one of the world’s top ten intellectuals.
Learning rational philosophy is more about the methods you use than where you start, the particular resources you use, or the topics you find interesting (you should pursue your interests and try to learn things that you will be able to usefully apply in your life). What matters is how much effort you put into learning (persistently over time), and whether you’re using that effort effectively. The key to effective learning effort is error correction. Mistakes aren’t effective, and building on mistakes (which is what most people do for most of their lives) can be hugely wasteful.
If you’re looking for and discussing errors, and you start with some bad ideas, that will be OK. You’ll end up investigating some contrary ideas after you don’t know what to say in a debate, or get asked a tough question, or get curious enough to survey alternative ideas.
Your approach to learning should be organized so there are Paths Forward for your mistakes to be corrected, and you aren’t overreaching. You should be trying to address all criticism of any idea you accept, and you should write down the reasoning (or endorse and take responsibility for someone else’s writing – there’s no need to repeat some work if it’s already good enough). Never ignore flaws, mistakes, or problems. Have high standards from the beginning and build up knowledge which meets those standards. Don’t learn things in a shoddy way and expect to fix the quality later.
How do you know which ideas are correct and which are mistaken? By critical debate. Argue the case, publicly. A criticism is an explanation of a flaw in an idea. Seek out ideas with no known criticisms. Nothing less will do. This is achievable using the philosophy knowledge I’ve recommended reading above, such as Yes or No Philosophy. You should also investigate rival ideas you think may be correct, and discuss them in the same way described above.
How do you know if you’re making progress? By whether you learn things, and they are clear in your mind, and your knowledge is effective in life. If you have trouble using an idea in your life, or putting it into words, or figuring out how it applies to a scenario, or answering questions about it, or debating the topic, then there’s more for you to learn there.