If there is no principled way to proceed, then we face the real possibility and prospect that philosophical inquiry itself cannot be coherently pursued. I think that this, perhaps grim, skeptical possibility is one that we philosophers must, if we are to be honest, take seriously. The very possibility of philosophical inquiry is thus, I believe, something that should always be in question for philosophers.--Michael Della Rocca "The Taming of Philosophy."
The original impulse toward a philosophical turn to history is a certain unease, perhaps bewilderment, at the 'live' options thought/taught available in the present.* These all must seem 'off' in such a way that constructive disagreement seems like a trap that will only make matters, well, worse. When one has a sense that one cannot explore the existing 'issues' or 'options' with conviction, one may then be moved to retrace one's teachers' (including one's temporally prior self) steps back to a moment where the older, live options become, as it were, alive again. This impulse once nourished and cultivated by study is, thus, accompanied by a certain wariness of the victors's tales official and informal), especially -- one realizes, when these are told not as partial accounts attentive to the effaced options, but as the unfolding and articulation of the (progressing) truth.
The previous paragraph is stylized autobiography. But it understates the terror of stumbling on the thought that the alternative to believing that one's teachers and so-called epistemic peers are in a non-trivial sense mistaken -- not just about the facts and what is intellectually promising, but -- in all their most important commitments, is the live possibility of one's own madness. (Let's call this the 'haunted thought.')
As a biographical aside, there are fin-de-siecle stances toward the history of philosophy inculcated by Dreben once at Harvard and BU and a neo-Wittgensteinian quietism that emanates from Pittsburgh philosophy, which have a family resemblence to what I have just described. In both instances there is an engagement with professional moves while simultaneously declaring their futility. That's like being a master magician, explaining the hard tricks of the trade to the novice in order to exhibit one's superiority at the most difficult tricks. (During my PhD, these fin-de-siecle stances, with accompanying magisterial forms of education, were well represented at The University of Chicago.) The probem with these stances is that while claiming to offer a cure, they merely suffocate the haunting thought. I needed to be immersed in contemporary, Lewisian metaphysics to be able to breathe again, and so landing a position at Syracuse saved my life.
The original impulse described above has a kind of hidden assumption: that one can be legitimately at ease with the taught/thought available, philosophical landscape; that one can step up and explore the next move within existing constraints or, more daringly, explore an alternative to the encountered research frontier. This hidden asumption when accompanying the original impulse toward the history of philosophy marks one as somehow abnormal. Until I encountered Della Rocca and his students it never simply occurred to me that the original impulse may also be accompanied by the thought that this unease, perhaps, bewilderment is the healthy response toward the diagnosis that at any given time, "philosophical inquiry itself cannot be coherently pursued." [The so-called, "grim, skeptical possibility.]
This is not the place to rehearse and evaluate Della Rocca's argument for the grim, skeptical possibility. (Personal interest: buy the book!) His account is a searching, critical analysis of certain recently privileged methods of philosophy.** Della Rocca speaks with a certain authority because he is also an accomplished practitioner of the crafts of philosophy.
But I wince at Della Rocca's 'honest.' It implies that much of professional philosophy, which leaves very little room to pause at the grim, skeptical possibility (after all, writing a paper about it as a contribution to so-called meta-philosophy, is oddly self-undermining), is, in a non-trivial sense, dishonest. It's not because I recoil from insulting or provoking my hard-working and productive peers. Rather, honesty and sincerity are the wrong, for lack of a better term, registers of truth for engaging with the grim skeptical possibility. To put my disagreement with Della Rocca, first, jokingly: one does not throw more truth at a skeptical possibility, and expect the possibility to disappear. Seriously, Della Rocca's grim possibility is subsequent truth; so, being honest at this juncture would only worsen the very possibility of philosophical inquiry.
* There are, of course, lots of other motives that may prompt the study of the history of philosophy, even professionally. These do not concern me here.
**One can read my own reservations about explication as an extension of his analysis.