"I used to think that establishing boundaries required strong emotional responses. I was wrong. Learning to say no and express oneself in an empathetic way is a valid alternative." James Agapoff (Twitter: @ dragonnovelist) recounts an experience that taught him about establishing boundaries, making compromises, and knowing when to keep his opinions to himself. This essay was published in the Teaching and Learning Moments column in the July 2019 issue of Academic Medicine. Read the essay at academicmedicine.org.