This is not about mussar. It is about when and how we allow situations to develop which present us with a choice between two evils.
Generally speaking, people make compromises and “choose between the lesser of two evils” only when, fundamentally, they consider both “evils” acceptable choices. This was the point of the analogy to a lawyer. For the lawyer, this choice simply does not exist – he must be on time, and he must wear a tie.
Here is another analogy: A bachur in yeshiva may want to choose the lesser of two evils: Skip breakfast (thereby compromising his ability to learn) or come late to seder (so he can eat). The fact is, he should wake up earlier. Several years later, the same individual (now married with children, and not afraid he might be asked to do gelilah) will never have a problem waking up on time for the early minyan. All that changed is whether his new situation allows for the choice to exist.
Obviously, there are exceptional cases where it is impossible to avoid such a situation; these, however, are few and far between. Most often, the choice only arises because the person’s value system allows this to happen. ????? ?? ?????.
If a Rebbe comes late or without a tie several times in his career, that’s probably due to circumstances beyond his control. [Incidentally, in such a case, I would probably go without a tie]. If it happens often enough that he wants to know what to do next time, that’s probably because one or both of these things is not important enough to him.
Not mussar; just objective analysis.