This post is personal, not in the sense that it reveals personal details that would usually be kept private, but in the sense that it's not intended to make universally valid claims, but instead only to report the experience of the author. (With the implicit hope that this experience is shared by others.)
That experience is this: I like philosophy, and I like board games, and the two activities don't feel all that different to me, and here I'll say something about why.
I feel guilty on revealing this (maybe the post is personal in that sense after all) because I seem to have both trivialized philosophy and unduly elevated gaming in a single unconsidered action. But I'll try to overcome that problem as I write this post.
I am having trouble tracking down where I got this idea, but my favorite definition of "game" (pace Wittgenstein!) goes something like this: A game is an activity whereby one or more people limit themselves artificially to certain rules, in pursuit of a goal that has no value independently of that activity. ("Artificially" here meaning the rules are not simply reducible to rules found outside the activity. The rules are special to the activity. Otherwise, life itself would be a game, and it's not, is it?)
Meanwhile, my favorite definition of Philosophy is one I made up, though there are clear shades in it of things several famous thinkers have said in the past. That definition is this: Philosophy is conceptual thrill-seeking.
Thrill-seeking? What I mean by this is the kind of thing we do when we ride roller coasters, or go bungee jumping, or chase tornadoes. What's in common here? We're putting ourselves into a position that forces us to be aware of how tentative our security is—but typically, we're doing so in a way such that our security is not really that much in question. We're simulating life-threatening loss of security, though not necessarily actually experiencing a life-threatening loss of security. (I say not necessarily, and put this in terms of what's typical, because thrill-seeking can involve greater or lesser degrees of actual danger. But most thrill-seeking activities involve numerous fail-safes such that the activities basically are safe.) Strangely, though we know we are safe, much of our reaction to the situation involves the same kinds of feelings we would have were the simulation actual—were we actually unsafe. It is this combination of feeling unsafe while knowing we are safe that allows for thrill-seeking to be a fun activity—and a valuable one.
Why is it valuable? We learn about ourselves, our limits. We can use the experience to prepare for genuine emergencies. We discover facts and ways of doing things which would not occur to someone in a totally safe situation. And so on. The utility of thrill-seeking seems fairly clear. It has basically the same value as exploration does, though what's being explored isn't a surface but rather a person or a community (in the case of communal thrill-seeking activities such as sky diving or mountain climbing.)
So what I'm claiming about philosophy is that it is a kind of thrill-seeking. Well, I'm reporting that that is definitely what it is for me, and I suspect it is so for many others as well. Even the kind of philosopher who builds intricate systems in defense of a dearly held religious belief (who you might think isn't thrill-seeking at all, instead doing something like building a fortress) I would say is likely engaging in thrill-seeking. For in Philosophy, there's no distinction between the architect and the construction worker. To plan out the system is to build the system. And the construction worker must climb out onto dangerous ledges, balancing on beams where a slight misstep will lead to terror followed by death. And so, therefore, when it comes to system-building, must the architect as well—for the philosopher fills both of these roles simultaneously. In defending a dearly held belief by building an intricate conceptual system and elaborating in in response to attacks, this kind of philosopher must often ask herself about the consequences of possibilities that are very uncomfortable for her dearly held belief. This can't help but be thrilling. And going out on these limbs has all the same value as thrill-seeking for her, allowing her to anticipate things that can't normally be anticipated, to create a new way of thinking about her self (or her system) and her/its limits, and so on.
Meanwhile, for me (and I'm sure at least some other philosophers) the thrill seeking aspect of Philosophy is much more direct. I like to think about personal identity because it is great fun to consider what it must be like from the inside to realize one has no continuing self. I may or may not become convinced that this is so, but more than half the reason I consider the question in the first place is to get that abyssal feeling of being on the brink of realizing one's own destruction—all the while knowing I am actually perfectly safe because my kids are going to enter the room in the next moment and whatever else is true or false about the metaphysics of personhood, I will be a father again (or at least, I will not be able to help but think of myself that way, and I am happy for that even if it turns out it is an illusion of some kind).
I've gone a little off topic, but to recap: Philosophy is conceptual thrill-seeking, and games are activities of following artificial rules in pursuit of goals with no value outside the game.
And on reflection, I think we can see the two things I just defined must share a number of similarities. What is the goal of bungee jumping? It is to hang in the air unsuspended. That has no value outside the activity of bungee jumping! Indeed, in most other contexts, it is absolutely disvalued! And, in order to bungee jump, one must wear a harness, and one must jump off a bridge (or other high platform). These are artificial rules! These are not things one must do just to live or be part of a community or anything everyday such as that. These are special rules one imposes on oneself artificially in order to engage in a particular activity—an activity with a goal that has no independent value outside that activity. (Engaging in the activity itself has utilitarian value as I argued above, but the goal internal to the activity is not valuable itself.)
Okay so then Philosophy is a game. Not a particularly new thought at all, but I think the thrill-seeking/gaming connection is an interesting addition to that notion anyway.
I started out talking specifically about board games at the beginning of this post. There's nothing particularly insightful about that—it's just that I've never been much of a physical game-player, my own personal style is much more (cripplingly) oriented toward the intellect, and so on. So since board games are a primarily intellectual activity, of course they are the kind of game that will feel, from the inside, most like philosophizing to me. I know this not to be universal—I know philosophers who encounter philosophy as an activity, and don't recognize any ultimate distinction between physical and intellectual activity. It's all stuff you do with your body. I recognize that intellectually—but like I just said, I recognize it intellectually.
Is doing philosophy more like playing a game, or more like creating a game for others to play? After all Philosophy isn't just about finding solutions to known problems (that'd be playing a game) but also about finding problems for known solutions (that'd be creating a game). The two activities probably aren't actually distinct for any problem that's really complicated anyway. So the answer is just "both," I think.