All too often, people who develop exceptionally astute insights into others remain mysterious to these others. Evidence for such asymmetric understanding comes from several independent domains. Striking asymmetries occur among those who differ in status and power, such that individuals with low status and power understand more than they are understood. We show that this effect extends to people who merely perceive that they have low status: individuals with low self-esteem. Whereas people with low self-esteem display insight into people with high self-esteem, people with high self-esteem fail to reciprocate. Conceptual analysis suggests that asymmetries in mutual understanding may be reduced by addressing deficits in information and motivation among perceivers. Nevertheless, several interventions have been unsuccessful, indicating that the path to symmetric understanding is a steep and thorny one. Further research is needed to develop strategies for fostering understanding of those who are most misunderstood: people with low self-esteem, low status, and low power.