To understand philosophy one needs to read few books, but I would like to suggest some guidelines that might suit the vast majority.
Be a Hedonist
At first, be hedonistic for philosophy before studying this subject. Let’ say you have started studying philosophy to be educated or for a cocktail party storytelling then you will learn nothing since you will never find it interesting and rewarding and eventually it will drive you to stop before starting your journey. It’s amazingly unlikely you’ll thoroughly enjoy Aristotle, Hume, Descartes, Heidegger, Hegel, and Sartre. Start your journey with love and passion only.
Find out which best describe you from below
1) “I want to learn more about the history of human thought on the most comprehensive level. I don’t care if the Greeks I read about have been improved upon, I want to know what Aristotle spoke and how later philosophers answered. I get why people warn me off, but I’m still driven toward an immense historical knowledge and I never get bogged down in technical reading.”
Read: A History of Western Philosophy by Bertrand Russell
2) “I’m interested in a philosophy that describes things clearly and builds technically upon those clear definitions. I’m interested in free-will and careful investigation into what can be recognized for sure and how it can be known.”
Read: Bertrand Russell’s The Problems of Philosophy
3) “While a glance shows the most interesting philosophy will be found in metaphysics and epistemology, I know from human nature that studies of ethics can be enthralling. I don’t weigh the search for meaning a ‘soft’ topic.”
Read: Simone de Beauvoir’s The Ethics of Ambiguity
4) “All I know is that the dog-eat-dog world is not satisfactory. I’m looking for something deeper, but typical religion doesn’t appeal to me. I’m interested in the philosophy of mindset, but I don’t know where to begin.”
Read: The Way of Zen by Alan Watts
If you chose 3 or 4, you can skip this. It’s a warning about options 1 and 2. And note that my bias away from 1 and 2 is acknowledged.
If you chose 1 or 2 (the “Anglophone” philosophy options), beware of a common pattern of distress in would-be philosophers. Douglas Hofstadter once wrote about a youthful vision that symbolic logic would unlock the secrets of the universe. It doesn’t. Words have limits, so be careful how much you invest in them. Nowhere is this concept better explained than in the following, highly recommended post by Paul Graham.
Most of the philosophical debates are not merely tormented by but driven by confusions over words. Do we have free will? Depends on what you mean by “free.” Do abstract ideas exist? Depends on what you mean by “exist.”
So, If you don’t want to discover how to think for yourself. Study different religious holy books as much as you could instead of philosophy. If you want to learn how to consider for yourself, start by learning how to think, and after you make that, you might choose to get around to studying what some other people have resolved, intending to challenge them, and yourself, to think better thoughts, and come up with better beliefs and ideas.