“Our job is to prepare them for the real world.” This statement is not an unusual, nor an unreasonable, justification for pedagogical decisions throughout legal education. The dual role of law school as both an intellectually challenging academic endeavor and a training ground for the profession places it at an intersection ripe for “real world” considerations. As one example, many professors argue that inflexible deadlines (and dire consequences should they fail to be met) are necessary preparation for legal practice. However, as many experienced attorneys will report, extensions are hardly uncommon in the practice of law. This Article argues that the ability to not only ask for an extension, but also to avoid procrastination, anticipate when an extension will be needed, and communicate professionally in that request, are skills that law schools must teach. The necessity of these skills, and their place in the law school curriculum, is a matter of professionalism, equity, and practicality. Bringing together educational pedagogy, the Model Rules of Professional Conduct, and actual cases of attorney discipline, this Article makes the case for extensions in law school—and in the “real world.”

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