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How and why do upper-middle-class and upper-class people go against the grain of accumulation? Answering this question is critical, especially in an era of extreme social and economic inequality, where wealth is accumulating rapidly for those who already have it and increasingly unattainable for those who do not. Existing scholarship reveals how the financially privileged make sense of their ongoing accumulation, but we do not know how or why people develop a countercultural relationship to money, choosing to “go down,” or to live communally in a capitalist society. To answer this question, I conducted 50 in-depth, semi-structured interviews with middle, upper-middle, and upper-class Americans who adhere to political and religious moral traditions that challenge accumulation and who strive to put these traditions into practice. I explore what kinds of people marry their moral frameworks and their financial practices, the “decumulative” and “downward” practices they adopt and choices they make, and the consequences of adopting a countercultural orientation to money within a capitalist society. I find that going against the grain of accumulation allows people to experience a more robust relational life and a "deeper" sense of economic security, one that emerges through actively distributing, rather than accumulating, capital.