I'm not suggesting that learning the rules isn't important. It's crucial. You must learn the rules. But learning the rules is the easy part. The difficult parts are two-fold: first, figuring out how rules really operate to decide the infinite variety of disputes that arise between human beings living in an infinitely complex world, and, second, figuring out how to use that understanding of how rules really operate to counsel and argue for clients in ways that best serve the clients' interests. Law isn't a matter of determining what is legal and what is illegal. It's a matter of figuring out how to operate within a system of rules that have consequences large and small, likely and unlikely, and judging best how to act given those consequences.
Contract law is primarily concerned with figuring out how the rules really operate to decide the infinite variety of disputes that arise between human beings in connection with the private agreements they make or seem to make among themselves. Inevitably, it will be necessary to the understanding of how those rules operate to consider how lawyers and clients, given those rules, act in the real world. But to begin, we have to focus on the rules and analysis. It is no easy task.
Edward H. Levi, in a law review article later expanded into a book, An Introduction to Legal Reasoning, introduces the complexities of legal analysis as well as anyone I have ever read:
[I]f the legal process is approached as though it were a method of applying general rules of law to diverse facts -- in short, as though the doctrine of precedent meant that general rules, once properly determined, remained unchanged, and then were applied, albeit imperfectly, in later cases [--] it would be disturbing to find that the rules change from case to case and are remade with each case. Yet this change in the rules is the indispensable dynamic quality of law. It occurs because the scope of a rule of law, and therefore its meaning, depends upon a determination of what facts will be considered similar to those present when the rule was first announced. The finding of similarity or difference is the key step in the legal process.Edward H. Levi, An Introduction to Legal Reasoning, 15 U. Chi. L. Rev. 501, 501-03 (Spring 1948)(emphasis added; citations omitted).
The determination of similarity or difference is the function of each judge. Where case law is considered, and there is no statute, he is not bound by the statement of the rule of law made by the prior judge even in the controlling case. The statement is mere dictum, and this means that the judge in the present case may find irrelevant the existence or absence of facts which prior judges thought important. It is not what the prior judge intended that is of any importance; rather it is what the present judge, attempting to see the law as a fairly consistent whole, thinks should be the determining classification. In arriving at his result he will ignore what the past thought important; he will emphasize facts which prior judges would have thought made no difference. . . .
Thus it cannot be said that the legal process is the application of known rules to diverse facts. Yet it is a system of rules; the rules are discovered in the process of determining similarity or difference. But if attention is directed toward the finding of similarity or difference, other peculiarities appear. The problem for the law is: When will it be just to treat different cases as though they were the same? A working legal system must therefore be willing to pick out key similarities and to reason from them to the justice of applying a common classification. . . .
It could be suggested that reasoning is not involved at all; that is, that no new insight is arrived at through a comparison of cases. But reasoning appears to be involved; the conclusion is arrived at through a process and was not immediately apparent. It seems better to say there is reasoning, but it is imperfect. Therefore it appears that the kind of reasoning involved in the legal process is one in which the classification changes as the classification is made. The rules change as the rules are applied. More important, the rules arise out of a process which, while comparing fact situations, creates the rules and then applies them. But this kind of reasoning is open to the charge that it is classifying things as equal when they are somewhat different, justifying the classification by rules made up as the reasoning or classification proceeds. In a sense all reasoning is of this type, but there is an additional requirement which compels the legal process to be this way. Not only do new situations arise, but in addition peoples' wants change. The categories used in the legal process must be left ambiguous in order to permit the infusion of new ideas. And this is true even where legislation or a constitution is involved. The words used by the legislature or the constitutional convention must come to have new meanings. Furthermore, agreement on any other basis would be impossible. In this manner the laws come to express the ideas of the community and even when written in general terms, in statute or constitution, are molded for the specific case.