Long ago, in a distant land, I was an earnest high schooler trying to educate myself. I discovered Kant and Descartes at around the same time, and read the Discourse and Meditations while I was just getting into the first Critique. At first, I wanted to read philosophy because I had a firm conviction that Christianity was true, and I wanted to find a demonstration of it from logic. I had read the Republic and thought it was wonderful, and Mortimer Adler told me that great books make great minds, so I was enthusiastic. I swallowed Descartes whole, believed in the whole cartesian project, believed in his path out, etc. Reading Kant, I found a development and challenge to that project and over the course of a year gradually had my hopes of proving Christianity dashed. Kant's system was right and beautiful and coherent, but it clearly showed that you can't even prove the existence of God, much less all of Christianity. But Kant throws a bone to the Christian, by pointing out that you can't prove his non-existence either, and this gave me a tool to use in arguments: anyone's non-belief is just as arbitrary as my belief.
Then a month or two after I finished with Kant, I came across Russell's history of philosophy and read his chapter on The Master. He was unkind. His treatment of Kant is dismissive and cuts right at the heart of the kantian project. I was devastated. Kant my hero, who had already smashed half the certainties of the world, had himself been smashed in under 10 pages, leaving no certainties at all. I gave up and read Dostoevsky, still committed to the "my arbitrary belief is just as warranted as yours" defense of Christianity.
What followed over the next year was a series of misadventures: a lot of Kierkegaard, some Epictetus, some Lao Tzu, some Rushdie, and more Kierkegaard. I defended Christianity with skepticism, but my notion of Christianity was vague and disconnected from my life. I believed that life has meaning, that the soul lives on, and that there is some being who cares for souls. I had a loyalty to scriptural literalism, but was willing to interpret things loosely in order to make them agree with my philosophical views. From Kierkegaard I had a strong sense of the importance of self-presence and resolute consciousness, and tried (and failed) to better myself by working toward "faith". Faith never came, and so I just cycled in and out of despair.
Because the whole original project of believing in something rational and figuring out the world from first principles had bottomed out, I changed my life goals. I wanted to be an academic instead, so I decided to go with continental philosophy and become good at that. I picked up Heidegger and spent a month reading Being and Time. By this point I had become aware of my tendency to instantly adopt all the convictions of whoever I was reading, so I was more careful with Heidegger. I kept in mind all the other people I'd read, and compared. Heidegger's approach to philosophy was novel and very powerful. The first principle at work in Being and Time is that understanding is an interpretive exercise. Given my experience of the plurality of internally consistent philosophical systems, that understanding was a function of hermeneutic prejudices made total sense (it still does). The question then became one of method, and I read Being and Time more as a methodological handbook than anything. Heidegger's method is brilliant. He begins by proposing an investigation, and then proceeds through a sequence of cyclical exegeses of the problem, each time broadening the scope of his analysis by introducing some new concept or aspect for consideration. There are few arguments in Heidegger, because he recognizes the futility of trying to prove a philosophical foundation. "They will say I assume too much," he says, "but they assume too little." There is logic, but the logic is that of interrelated ideas unfolding various aspects of each other. Truth, he says, is not best understood as adequatio res et intellecta, since we have a degenerate view of "res" and "intellecta" and our notion of "adequatio" is absurd. Instead it is the self-disclosure of things.
There are great faults in Heidegger, and the core of Division II is stolen from Kierkegaard, but as a methodologist he is brilliant. His treatment of hermenutics and his critique of cartesianism (both in Division 1) are both among the best philosophical analyses I've ever read. Where Kierkegaard had gotten past the either/or of Kant and Hegel by asserting that truth is inwardness or individual subjectivity, Heidegger points out the faults in the entire cartesian problematic and restores a hermeneutical primacy to the structures of everyday existence: community, care, equipment, goals, etc. He does this not on the basis of a self-satisfied appeal to "common sense" or "the obvious", but because he finds the modern exegesis of reality ultimately inadequate. To talk about things the way Descartes does or about subjects the way Kant does is unrealistic, on one level because this is simply irrelevant to the way they actually present themselves to us. But even more than this, Heidegger's critique centers on the fact that the cartesian and materialistic modes of speech are generated by intentionally mutilating one's gaze on the world, creating perspective which intentionally ignores the way things ordinarily present themselves to us, and so reconstructs reality based on fragments of things, instead of their wholes, to produce a weird vision of the world totally detached from what we actually live in.
After Heidegger, my philosophical attitude was much more optimistic. I had a way of thinking about pluralism and, through hermeneutics, a way of adjudicating between rival claims to truth. I had a new sense that proof was not the best method in philosophy: that to convince someone of something you mainly have to show them what you see. Foundationalism and the quest for certainty had had their day, and had by their own standards shown themselves fruitless. Now there was something new that was capable of taking hold of the world and dealing with philosophical problems. I took a seminar that fall on Hermeneutics and Critical Theory, for which we read some Gadamer. This developed the project further. Gadamer explains intersubjectivity and the adjudication between radically different worldviews in a way that Heidegger does not. Furthermore, Gadamer's critique of the enlightenment is much less obscure than Heideggers, and exposes the implicit epistemological inconsistencies in the project.
The next term was my introduction to French philosophy, which I delighted in. I realized how fun philosophy could be when it was totally divorced from reality and wrapped up in logic (Derrida), and I saw the power of Nietzsche's genealogical method applied to history (Foucault). It didn't do much else for me. Meanwhile from Heidegger and Kierkegaard I had a received a neat little tool for assessing the practical value of customs behaviors and objects, and assessing the significance of things. This was repetition. SK has a wonderful little novella about the problem of Repetition, which you should read. Significance comes from the ability to sustain an ever shifting but nonetheless constant action or affirmation through time. In life this takes the form of little rituals: the way a meal is consumed daily, the rituals surrounding it — in society this takes on larger forms. And of course I was interested in religion. (I won't fill out the details here, I assume you can see how the connection works.)
After this period I was introduced to Newman and Chesterton and though I continued to tried at mastering Kierkegaard, I was not very optimistic. Under the influence of a friend, I convinced myself that philosophy was dead and needed to be abandoned. Fortunately the ladder of philosophy had brought me up to these heights, but it was time to kick away the ladder and read G.K. Chesterton and more C.S. Lewis. I was an idiot, and I paid for it dearly in general anxiety and self-loathing, not to mention a huge amount of wasted time fretting over absurdities.
I entered the Church, which did a lot of things for me. It gave me a new and more coherent understanding of history. It explained for the first time what Christianity actually was. It gave me a lot of joy and love and (in time) courage (oh, and grace). But aside from this I was in dire straights for a while. I had this idea that I should immerse myself in Balthasar, but I had no motivation to do it. People kept telling me to read Ratzinger, but I found him unappealing. What was there to respect? I could never get myself to read contemporary authors. They were unproven, and I wanted great things. I bought the Summa out of a sense of duty. It was the obvious thing to do, though Thomas's style is tedious and impossible to get into. Meanwhile I just affirmed everything and began to read up on catholic dogma.
[to be continued, maybe]