As a young teen I wanted to start with all of Plato’s Dialogues (yes including Parmenides, which I loved, but I didn’t finish The Laws) plus the major works of modern philosophy. I used the old John Hospers text to identify Descartes, Leibniz, Spinoza, Hobbes, Locke, Berkeley, Hume, and Kant. I read some Aristotle too, although he bored me. Then I read lots of Karl Popper and Brand Blanshard, the old-fashioned defender of rationalism and critic of positivism. I gobbled up George Smith and Antony Flew on atheism. I was influenced by Ayn Rand’s moral defense of capitalism, though I was never impressed by her as a philosopher.
Much later I read Nozick, Rawls, and Parfit. Parfit made by far the biggest impression on me. The other two, however smart, seemed predictable.
In graduate school I read Quine avidly. George Romanos’s book on Quine I found more useful than any single Quine work, although Word and Object and the essay on "Two Dogmas of Empiricism" are the places to start. Quine remains a major influence, including on how I think about blog posts. Which thicket of assumptions might lead one to a possible conclusion? I took a class on philosophy of language with Hilary Putnam and developed interests in Kripke and others, but they never displaced Quine in my affections. I developed a fondness for William James. From Rorty I saw more value in the Continentals, although I prefer to misread them. I flirted with the early German romantics and their rejection of philosophy, at times mediated through J.S. Mill.
Later experience with Liberty Fund interested me in "deep" readings of Montesquieu, Tocqueville, Maimonides, and some of the other "Straussian" texts. I’ve never been a Straussian, though. I’ve made attempts to understand Heidegger but without any success.
Right now the philosophy journals I read are Ethics and Philosophy and Public Affairs. When it comes to metaphysics, mind-body problems, and the like, I prefer books, usually of a semi-popular nature. The academic debates on these topics are too rarified to interest me very much.
That is my path, in a nutshell. I don’t pretend it is an optimal sequence for others.
The bottom line: I have learned to focus on the philosophy which clicked with me at the time. The rest was just so much blah blah blah. Philosophy books are more like self-help tomes, or fun record albums, than they let on.
Any suggestions for how our reader should choose a path?