We must all, from time to time, make hard personal choices—to get married or divorced, go to law school or drop out, support a parent or renounce a friend. If we find such choices difficult, it is usually because the alternatives seem in some fashion incommensurable. Each has its own balance of advantages and disadvantages and there is no common metric that permits us to assess their relative attractiveness in a decisive and unambiguous way. The choice that we must make cannot, therefore, simply be a matter of deduction or calculation, as utilitarians sometimes suggest. Nor is it a matter merely of waiting for the appropriate intuition, the one that will tell us what to do. We tend to deal with our personal dilemmas, even the intractable ones, in a more active and methodical way than that. Choices of the sort I have in mind call not for deduction or intuition but deliberation, which is another name for judgment. Indeed, it is precisely in situations of this kind, where the choice to be made is between alternatives not easily compared, that our reliance upon the faculty of judgment is most evident. In exercising this faculty, what exactly is it that we do?
The answer, I think, is something like the following. When faced with an important personal decision, I am frequently required to make what amounts to a choice among competing ways of life—different ways of life that might be mine though none of them, by assumption, yet is, at least in its fully developed form. To make such a choice, I must explore the alternatives in my imagination. That is to say, I must make the effort to see and feel, from within, what each would be like were I to choose it rather than the others. The effort to do this is not unlike the everyday attempts we make to understand the experience of other people, and it resembles, too, the attempt that historians and anthropologists make to understand those who are remote from them in time and cultural attitude. In these latter cases, of course, it is other people and not ourselves that we are struggling to understand. But the self I will become if I embrace a certain way of life may very well seem, at the moment of decision, something of a stranger too, a person both familiar and remote in the way that other people often are. So to grasp the possibilities before me, even where they are only different ways of living my own life, I need the same sort of imaginative powers that are required to make sense of someone else's situation or experience. What is needed, above all else, is a certain measure of compassion, in the literal sense of "feeling with." I must make the effort, in choosing a life for myself, to feel along with each of the persons I might become the special cares and concerns, the risks and opportunities, that give the experience of that possible future self its own distinctive shape.
(Anthony T. Kronman, "Living in the Law," The University of Chicago Law Review 54 [summer 1987]: 835-76, at 851-2 [italics in original; footnotes omitted])
Keith Burgess-Jackson, J.D., Ph.D. 