It is commonly accepted that we should and often do learn from our mistakes, and it is also quite common to be afraid of making mistakes. International educators are no exception to the experience of learning from mistakes. This author describes a professional meeting where several of the attendees who had been in their field for decades shared some of their greatest lessons reaped from mistakes. At the gathering it was learned that, while cultural gaffes were common, so were mistakes the attendees had made in working with students, bosses, and co-workers: not listening carefully to all sides of a problem, rushing to conclusions, making poor decisions, and so on. This led to wondering about the larger field, and to ask the question of others, "What have you learned from your professional mistakes?" This article comes out of that research. Participants in this project were recruited through requests made on international education listservs. In the end, 40 people answered an online qualitative survey and twelve people were interviewed for deeper insight and information. The results show that the work of an international educator is challenging, due to complex situations across multiple cultures, conflicting values, and paradigm-pushing educational encounters. It is to be expected that these professionals will make mistakes. The overarching lesson here is that one should not be fearful of tripping up, but rather be open to learning from the mistakes made.