I can’t possibly examine my life unless (1) I’m able to take a reflexive stance toward my desires, beliefs, and values and unless (2) I’m willing to test those desires, beliefs, and values. The first condition concerns my capacity to reorient myself toward my life while the second condition stakes the possibility of my thinking well on the indispensable virtue of courage. The paradox of the philosophical adventure has ever been that philosophy is available to any basically, decently rational person but is practiced, and has only ever been practiced, by a select few.

Condition 1: The Reason Why Humor is a Saving Grace. To see why humor is so important to one’s capacity for philosophical self-reflection, let me tell you a story. It’s around noon, and I’m running in Central Park. I’m headed north, not more than a mile into my run by this point, when I see a black guy listening to Janet Jackson, walking along with a boombox on his shoulder. This is patently absurd, I think, completely incongruous with the arcadian surroundings: the autumn leaves, the blighted trees, the gently sloping hills, the bubbling brooks. (This is a second joke, by the way, a spoof of the picturesque, a parody that  Austen was already making of the picturesque aesthetic tradition back in the early 19th C.) Or could it be that running in the park is, in the grand scheme of things, the more absurd thing to do?

Humor of this kind implies that we’re able to stand back from our lives and look at ourselves while we’re in the midst of a scene. It’s as though we were saying “action” and “cut” at the same time. The general test is whether you have the capacity to take any scene you’re in as potentially comparable to the one with the man holding the boombox or the guy laced to his running shoes. The most familiar scene can, at any moment, turn awry: here the too earnest man on the subway; there the girl (still…still!) wearing Ugs at the grocery store; over there the couple in Midtown both scrolling through their BlackBerries, both miffed at the traffic; and over there the guy with the 10 year old cashmere sweater who’s clucking over his herb plant and musing about the fan behind his armchair. God, what a fool that guy is. Oh, but that’s me!

Once we stand back from the flux of our lives, we show ourselves that we’re able to stand back from the brink. Although life is serious (the first lesson of growing older, the lesson that the young have yet to learn), our lives are not so serious that they will go on indefinitely (the second lesson: facing death). Standing back is tantamount to learning, paradoxically, how to live otherwise but also how to die well. How to live otherwise because in this self-reflexive moment we reckon that our lives, having gone this way, could still go on differently from here on out. We are indeed the klutzes who trip on the sidewalk (the actors in scene), but we are also the spectators who look on in amusement (the spectators just off scene) at the klutzes who trip about. But then also how to die well because we practice the art of letting go of this self and then this self and then this self, giving each a slightly comic turn as we say good-bye to each in turn. As we, now the spectators, say our goodbyes…to each in turn.

Sadly, most will remain gripped by the moment, held fast by the pull of the scene, unable to pause and say “cut” and try things over a different way. Unable to step out of character, they may very well go under. Or, Zinfandel in hand, become bored with life. About a week ago, I had to say good-bye to one conversation partner because, in his early 20s, he was simply too earnest, simply couldn’t fathom how to take a step, a half-step, a quarter step, out of his life. Rather, he was caught, pre-philosophically, in the middle amid the buzz and whir. To him, nothing could be amusing and nothing much done.

Frankly, there’s nothing that philosophy can do for someone who does not come to it with open arms, dancing shoes, and a very limber back.

Condition 2: Really? I Mean, Really? Are You Really Sure About That? A while back, I’d been working with one conversation partner for a couple of months before she’d told me a story about a contract that she didn’t fulfill. Why, I asked very gently, didn’t you complete the project. Because, she said, she had the intuition that something wasn’t right about it and that this was God’s way of testing her. To be clear, this woman was highly intelligent, had finished advanced degrees at Ivy League universities (a Ph.D. in fact), had a warm demeanor, was very likable, and could provide clear analyses of her acquaintances, family members, and the broader world. There was a good deal to be said in her favor. And yet, her religious worldview, which was pretty sensible on the whole, didn’t allow for some “basement level” philosophical considerations. I didn’t feel as though I could ask whether this was really a test and whether the scenario didn’t admit of better reasons, fuller explanations, and more accurate accounts of motivation and desire. Once we hit a certain point in our conversations, there was no room for the “Really, are you so sure about that?” question. Wisely, I sat quietly and, weeks later, said my good-byes.

Depending on the context, the “Really?” question can mean: (a) Are your beliefs true? (b) If they are true, are they justifiable? On what grounds? (c) How consistent are your most basic beliefs? How well do they ‘hang together’? (d) Are these desires primary, secondary, tertiary? (e) How about those values: do you really value (e.g.) worldly ambition above all else, because you know, don’t you, that you’re going to die? See this skull that’s–waha!–in my hand? (f) Above all, are you really really committed to, really all in this form of life? Are you in it, all in there, wholeheartedly?

Bear in mind that the “Really?” question doesn’t entail any particular conclusions. On its own, it doesn’t imply letting go, holding on, or leaving everything up to doubt. More humbly, it suggests a holding up to inspect for a time, a holding up long enough as if whatever were being held up were a breath held for a moment or two in mid-breath. We don’t know yet where the “Really?” question will go, but we do know what it signals. It tells us–tells the few courageous, blessed philosophical souls–that we’re not already there. And perhaps this makes us laugh because everyone else assumes as much. We laugh because we’re less unwise now than we were before. Thank God.