If you’re a serious student of philosophy, ignore all videos and summaries of philosophy books until you have read the actual book—or at least until you reach an impasse in your understanding of some concepts.
Even if you find some concepts difficult to understand, you ought to think on your own and not make a habit of having your thinking done by someone else.
Think for yourself as much as you can. By doing this, you will train your mind to solve difficult philosophical problems, and it will develop your own creative thinking by arriving at solutions to philosophical problems on your own.
I will not recommend a history of philosophy at the start of your philosophical journey until you get a grasp of the basic philosophical concepts that are the bedrock for the rest of the ongoing philosophical conversation. You cannot meaningfully be a part of the conversation if you only have a “historical” approach to philosophy. You need to actually understand the concepts and be able to argue why those concepts are true or false with justification.
That said, the first philosophy book to read is The Apology by Plato. This is the easiest and simplest introduction to philosophy that I can think of.
After that, read either Euthyphro or Ion by Plato. After that, read Crito, Meno, and then Phaedo.
After that, read The Republic by Plato. The Republic will bring together many of the different concepts and philosophical problems presented in Plato’s dialogues and is an essential part of the philosophical conversation.
After this, read Aristotle’s Ethics. Now, Aristotle is going to be more difficult to read than Plato in some respects; nevertheless, this is a book that you want to master; it will sharpen your thinking for when you encounter much more difficult philosophical texts. This is a book that will send you on your way towards becoming a true philosopher. (I linked the Signet Classics version of the Ethics because it gives you the essential parts of Aristotle’s Ethics and you get his other works along with introductions to each work; however, if you want to get the full Ethics by all means, get it.)
If you are up for a short challenge, then read The Categories by Aristotle, though I would try reading this in tandem with Aristotle’s Ethics. Learning about the categories will help you understand in depth Aristotle’s manner of metaphysically organizing things.
After this, you can read Politics, On Interpretation, Poetics, Posterior Analytics, Metaphysics, or even Physics. Here, it all depends on what you are curious about or what you think is important to understand. (An important note: I think it is good to read about the presocratic philosophers before diving into Aristotle’s Metaphysics or Physics.) Another recommendation would be to read a book on basic formal logic, i.e., learn about syllogisms, deduction, induction, fallacies, etc. Here is a recommendation: “Logic: A Complete Introduction.” Or you can go back and read some more Plato. Whatever you prefer.
After studying what you think are the essential parts of Plato and Aristotle, you can pursue theology or more philosophy. I will not recommend any theology here since the purpose here is to focus on philosophy. Further, it is here that I will recommend Will Durant’s “The Story of Philosophy: The Lives and Opinions of the World's Greatest Philosophers.” However, you can find the audiobooks of his book for free on YouTube.
After reading the essential works of ancient philosophy, it is time to proceed to modern philosophy, which entails reading René Descartes’ Meditations on First Philosophy and an optional work of his, namely the Discourse on the Method.
Of course, Descartes is responding to a certain philosophy in his works, namely empiricism, so it is going to be important to understand empiricism, which will entail understanding Hobbes’ account of how we attain knowledge—his epistemology, that is—which he expounds on in the Leviathan.
After that, read Leibniz’ Monadology and Discourse on Metaphysics—or read Spinoza’s Ethics—or you can read both. Both Leibniz and Spinoza are rationalists; however, the two have different approaches to understanding reality within the rationalist paradigm.
After this, consider reading the empiricist David Hume’s “A Treatise of Human Nature.” After Hume, you should then read Immanuel Kant, who proposes an entirely new paradigm in response to the problems of both empiricism and rationalism, namely “transcendental idealism” in his Critique of Pure Reason.
After Immanuel Kant, consider reading Georg Wilhelm Friedrich Hegel’s “Phenomenology of Spirit.”
Finally, consider reading Friedrich Nietzsche. Here, I recommend a compendium of his work: “A Nietzsche Reader.” Now, in some way, Nietzsche's philosophy should not be difficult to understand since if you grew up in the Western world and went to public school, then you probably already have a materialist/Darwinist worldview, so Nietzsche’s philosophy should be, I think, intuitive.
This isn’t a strict list to adhere to; it is just an outline to illustrate and help you understand the great philosophical conversation of the last couple thousand years. However, I would stick to understanding the essentials of Plato and Aristotle; that, I think, is a must for any philosopher.
Now, I don’t expect you or anyone else to actually read and understand everything that these philosophers wrote. We have to be realistic; that is why one has to learn how to reduce the various philosophies to their axioms or main points. Once you read more and more, you can learn to parse out these points; thus, you don’t necessarily have to spend one lifetime trying to understand one philosopher. That would be dumb and boring! Learn the essentials and get moving. We don’t have multiple lifetimes to spend on any one philosopher.
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