In my view, there are interesting questions about art, and there are boring questions about art. Boring: What Other Art Does this Look Like? (ie, any sentence that starts with "the work is reminiscent of,"), though I guess if you can't see the piece in question yourself, knowing what it resembles can occasionally be useful. Is it Art in the First Place? discussions get old fast, and tend to result in circular, infuriating conversations. And my least favorite: "This is the Most Important [painting/sculpture/whatever] of the [arbitrary time period]" which I hate because such assertions are gimmicky and impossible to prove.
The questions that really keeps me up at night always center on why I like what I do, and how that can best be articulated. What makes it good? Or what makes it flawed? Why can't I explain what I think is good without sounding like a jackass? If you actually have something to say, is drawing the best way to say it? And so on.
Then there's the fuzzy subject of talking about your art-making experience, which sounds like something that should be interesting, but isn't, at least for me (for Victoria Gaitan, the opposite is true). I've always been astounded that I can take a drawing I adore, and find myself with absolutely nothing to say about it, (which I know you aren't supposed to admit), or that while the art itself may be interesting, its production has made me remarkably dull; my evenings have been spent in solitude drawing for the past couple of weeks, with no funny anecdotes to speak of. But that's the life I have now. The process is wonderful, and the results are fun (and incidentally, I highly recommend All the Devils are Here, One Day, and Freedom, which I've happily listened to while working) but when I try to explain how and why, I got nothing.