In the author's role as an academic dean, she frequently meets with students on probation who have not yet learned how to fail and are consequently paralyzed academically. One of the most pivotal skills for a student who wishes to succeed in the academic arena is the ability to fail well. "Good failing" requires the strength to make use of a self-generated mess. Of course after the mess, the learning can begin, and that is precisely what the students whom the author works with discover. It is a lesson more valuable than the lessons learned in the courses in which they will ultimately earn A's. The energy, even courage, to rethink a failed piece of work, write, rewrite, inquire, and respond to the comments and questions of a critical reader is crucial for anyone aiming to excel in college. Moreover, the shame and embarrassment of producing a less-than-perfect paper or exam becomes a handy shield against the hard work it takes to build on failure. Unfortunately, more often than not, students placed on academic probation because of a poor performance in their first semester of college resisted turning in an imperfect paper, completing a flawed exam, or appearing in subsequent classes because they were too paralyzed by criticism to prepare or move forward. Their self-defeating actions stem from fear of criticism. In short, they are bad at failing. The author contends that the role of a good adviser or dean is to engage the student in dialogue, to encourage her to examine the causes of failure, to give her room for honest self-assessment, and then to guide her toward taking responsibility for improvement. The goal is to help students listen to themselves and make the needed connections so that their failure fuels success.