Prudence is not the most attractive of words, and it is not one I find in wide currency– and certainly haven’t found it in any of the lists of 21st century aptitudes I have been surveying.    I know it partly went out of favor thanks to Dana Carvey’s frequent mocking of the first President Bush– “wouldn’t be prudent.”  

But David Brooks, whom I find a great guide, writes today about prudence, and I am struck by the way he describes the word, and how well the word captures so many of the intellectual capacities I think we need to be developing in ourselves and our students in the 21st century. 
To quote: Prudence “is the ability to grasp the unique pattern of a specific situation.  It is the ability to absorb a vast flow of information and still discern the essential current of events– the things that go together and the things that will never go together.  It is the ability to engage in complex deliberations and feel which arguments have the most weight.   The prudent leader possesses a repertoire of events, through personal involvement or the study of history, and can apply those models to current circumstances to judge what is important and what is not, who can be persuaded and who can’t, what has worked and what hasn’t.” 
In writing these words I am reminded of a description of Frank Boyden’s leadership style.  Boyden, among the most legendary of independent school leaders, headed Deerfield Academy for 66 years, from the age of 22 to 88; he is brilliantly profiled in McPhee’s book, The Headmaster (originally published in the New Yorker).    It is just a short line, almost a throwaway, but I always think it contains important insight about smart leadership.   Boyden, McPhee writes, “has the ability in conversation to give his undivided attention, and the perception to understand the implications of practically anything that is said to him.”   
This perceptive ability, I would suggest, is closely related to Brooks’ notion of prudence– the ability to discern what is important, to recognize patterns, connect dots, evaluate the implications in any proposed course of action.   And I think we can seek to teach this: provide students challenging dilemmas or complex problems, and ask them to think them through, identify multiple pathways or remedies, and then evaluate each.    We would be instilling this important quality of judgement which is best captured in what is an old-fashioned word, prudence, but which is also a critically valuable 21st century aptitude.