A successful private company re-engaged my services in connection with its election to pay out participants in its ESOP (which I had helped install many years previously) and terminate the plan. As I reviewed the situation, it occurred to me (along with the company’s accountants) that, were the ESOP to terminate, leaving only natural persons and US residents as investors in a single class of the company’s common stock, the company would become eligible to elect to be taxed under Subchapter S of the Internal Revenue Code, meaning that Federal income tax would not be leveled on the company’s taxable income. Major savings were in view. I huddled with the company management and its accountants to review the situation and we quickly concluded that the window for making the S election for the year in question had terminated several months previously. Had it been timely made, the election would have become operative as soon as the ESOP no longer owned company preferred shares. In the course of the conversations I made a suggestion which proved to be fortuitously productive; while not a tax specialist, it had occurred to me earlier in my career that a well rounded lawyer, one focused on so-called ‘green goods’ (transactional corporate finance), needed a basic grounding in all the accoutrements … executive compensation, ERISA, partnership and LLC structuring; and partnership federal tax. The point of this narrative is that the ‘value add’ proposition is necessarily bottomed on skill sets which go well beyond the narrow focus on one slice of the business … well beyond activities which, as one of my former colleagues puts it, are largely “clerical.” The lawyers, hoping to attract compensation tied to “value,” needs to be literate (if not expert) in the each of the disciplines likely to be encountered by his paying customers. One way to acquire and maintain that level of familiarity is to add to a lifetime of practice the ‘humbling’ experience of teaching, researching and writing in the various sectors involved. I say ‘humbling’ because there is no better way to expose what you don’t know on a given subject than to undertake to teach it and/or to research and write on the subject. Students, indeed, are often the quickest to pounce on errors … and they do so gleefully. The short of the matter is that I was able to call on prior experience and come up with a solution. The IRS, if approached openly and respectfully, is prepared ex post facto to extend the time limit, given a plausible excuse, for filing the S election. It did so in this case, after, of course, a fair amount of give and take. The client was considerably better off.