Inequality, wealth and how it shapes cities, and the lives of those who live in them, have long been prime objects of research in social sciences. However, investigating the lives of the wealthy city-dwellers is a challenge for researchers as it comes with many methodological hurdles. In her book Uneasy Street: The Anxieties of Affluence, Rachel Sherman overcomes these obstacles to offer a rare analysis of New York’s upper class at the crossroads of sociology and psychology. Drawing on in-depth interviews that she conducted with fifty affluent New Yorkers—from hedge fund financiers and artists to stay-at-home mothers— the researcher examines their lifestyle choices and understanding of privilege. Rachel Sherman upends images of wealthy people as invested only in accruing social advantages for themselves and their children. Instead, these liberal elites, who believe in diversity and meritocracy, feel conflicted about their position in a highly unequal society. As the distance between rich and poor widens, Uneasy Street not only explores the lives of those at the top but also sheds light on how extreme inequality comes to seem ordinary and acceptable to all.