While attending evaluation and feedback is crucial for resident development, perhaps equally important is a resident’s self-assessment. If a resident does not accurately self-assess, clinical and professional progress may be compromised. This study compares emergency medicine (EM) resident milestone evaluation by EM faculty with the same resident’s self-assessment. Residents over-estimated their abilities in every sub-competency assessed, which underscores the importance of feedback and assessment transparency. More attention needs to be paid to methods by which residency leadership can make residents’ self-perception of their clinical ability more congruent with that of their teachers and evaluators.