Kronman's account of deliberation about ends focuses on those "decisions ... [that] present me with a choice between incommensurable ends -- ends so different in kind that it seems meaningless to treat the conflict between them as a problem of tradeoffs with a quantitative solution." (64) These, then, are the issues that cannot be resolved by calculation, even Herculean calculation, because there is no scale of value on which to make the calculations.
I'm not sure that this category actually exists. It may well be that no universally accepted scale of value permits me to measure the relative benefits of, say, liberty versus security. But that doesn't mean that these values are incommensurable for me. I may conclude that for me liberty is more important than security, or that this particular form of security is more important than that particular aspect of liberty. In doing so I have made the incommensurable commensurable, at least for me.
Moreover, Kronman himself ultimately seems to say there is a criterion for making choices among incommensurable values. "The mark of a wise judgment in the personal sphere is its tendency to promote the condition of integrity." (97) But if that is so, then "promotion of integrity" is the scale on which otherwise incommensurable values can all be rated. Not only can incommensurable goods be rated on this scale, but they should be -- assuming that wisdom is what we seek.
But if the subjective experience of true incommensurability is rare, still it may exist; I may not be able to say that liberty is or is not more important than security to me, and so I may be hopelessly uncertain about how to choose between them. So how should I deliberate about them, either in an effort to find commensurability after all or in an effort to make the choice I must make despite not finding any scale of judgment to rely upon?
Kronman answers that "part of what one is attempting to anticipate in imagination are the causal consequences of the various choices one might make." (69) So if I am considering, say, whether to "help my aging father fulfill his wish to die" (one of the examples of fundamental choices that Kronman mentions, at 65), then I would certainly want to know whether I could successfully assist him, and whether I would likely endure prosecution or imprisonment as a result. But, Kronman writes, "that is not all one hopes to learn by means of this imaginative exercise. One hopes also to gain some understanding of the alternatives in another sense, to learn something about the experience of actually committing oneself to them." (69) From this proposition, Kronman develops his argument for two critical virtues of deliberation, sympathy (to understand and feel the attraction of the various lives that might flow from my choice) and detachment (to be able to stand back and judge among those lives). Without "entertaining with a combination of compassion and detachment the values that define [these alternatives'] internal points of view," one cannot fully understand these choices, any more than a child can understand the internal experience of being drunk. (73)
The case Kronman makes for the value of such deliberation is persuasive, but only to a point. Valuable as such reflection may well be, it may not be what people who have good personal judgment actually undertake when they are making their decisions. Kronman doesn't seek to offer survey research or similar evidence of what good decisionmakers actually do. If we look instead, as I take it Kronman does, to our own sense of how we decide -- not an illegitimate source to rely upon, especially since survey research evidence may be hard to come by -- I suspect that Kronman's detached but sympathetic exploration of the values associated with the lives our choices will open up or preclude simply isn't a central focus of what most people think about when they are making many profound decisions, for at least three reasons.
First, many profound decisions are made in moments where detachment is unattainable. To take an extreme example, people facing the death penalty cannot make detached decisions about whether or not to plead guilty, yet they must choose. Many other choices, often involving much happier emotions and less acute circumstances, also seem intrinsically "attached" rather than detached.
Second, some profound decisions don't seem to turn primarily on future life-visions. Instead, they may turn more on present experience. "Do I want to change my life" is a question that certainly raises issues about what life I might have if I do or don't change this one; but it may turn most on whether I like the life I have right now. Or these choices may turn on issues of morality rather than prediction. Some choices certainly are about shaping one's future life; but others -- such as the example Kronman raised of assisting one's father in ending his life -- seem to have less to do with one's own future life than with the morality of helping someone else end his.
Third, and perhaps implicit in some of what I've said, I suspect that if we ask people (including ourselves) how they make decisions, we won't find, as a matter of fact, that the key element of the process is an effort to imagine their future lives with compassion and detachment. It seems to me, at any rate, that in clinical law teaching about client counseling, the bulk of what lawyers are urged to do with their clients is to help them accurately assemble a full list of the pluses and minuses of each available option. A part of that may be to ask, for example, how the client expects she would feel about a particular choice years later, but I don't think questions like that are usually seen as necessarily the most important ones.
Of course, the counseling lawyer's focus on the prosaic may just be a vehicle for assisting the client to make an ultimate, more profound judgment. Or the focus of both lawyer and client on the prosaic may be a sign that the decisionmaking lawyers and clients engage in (or at least that clinicians have urged lawyers and clients to engage in) is less profound than it ought to be. Or it might even be that the kind of decisionmaking most people engage in, with or without lawyers, is not as profound as it ought to be. Kronman is trying to describe what the virtue of deliberation entails, and he is by no means committed to saying that most people display this virtue very fully; in one of a number of remarks to this effect, he says of practical judgment by politicians: "But it is what every politician who hopes to be a statesman must aim at as his goal, and if its objected that far fewer succeed in this effort than fail, a good reply would be Spinoza's famous observation that 'all noble things are as difficult as they are rare.'" (106)
But I'm not persuaded by that response. Certainly it isn't valid to the extent that, as I've just suggested, some choices are intrinsically un-detached while others are reasonably viewed as involving primarily issues other than future life-visions. Beyond that, though, I find myself just unconvinced that the deliberative focus Kronman highlights is the primary tool for resolving profound life-choices. It seems to me that people in fact make decisions by quite a range of methods, and I think it is quite possible that other questions than the ones Kronman underlines will in fact, for many wise decisionmakers, provide a framing that is equally or more valuable.
To me, what this adds up to is that the case for the proposition that "practical wisdom" consists above all of a combination of detachment and compassion in the envisioning of alternative life-paths simply isn't proven. Why does this matter? Because if lawyers' distinctive virtue is practical judgment, then we need to know accurately what that virtue consists of, so that we can do our best to attain it and (if we're teachers, or mentors, or supervisors) to help others achieve it as well.