In a rapidly changing world, with boundaries of statehood, citizenship, influence and authority difficult to discern, attempting to interpret society is a necessary but uncertain enterprise. Using our diverse experience as heads of contemporary institutions, we explore the limitations of social interpretation, suggesting that those who are trying to make sense of society use their organizational and group memberships as organizing contexts while they listen to and negotiate the differing interpretations of others. Amid the pressure of conflicting roles and interpersonal projection, providing structured spaces that are free from interpretation may be crucial for individuals to locate themselves and claim their unique perspectives. Those who interpret society should be ready to notice their limitations.