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The Free Press
Things Worth Remembering: Money Can Ruin Your Life
Things Worth Remembering: Money Can Ruin Your Life
Betty Field Dancing the Charleston in "The Great Gatsby." (Bettmann via Getty Images)
I was born into poverty, and I believed wealth meant happiness. But F. Scott Fitzgerald taught me that prosperity can destroy you.
By Rob Henderson
03.09.25 — Things Worth Remembering
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The Free Press
The Free Press
Things Worth Remembering: Money Can Ruin Your Life

Welcome to “Things Worth Remembering,” in which writers reflect on wisdom from the past that we should commit to heart. This week, Rob Henderson, author of Troubled and friend of The Free Press, remembers a short story by F. Scott Fitzgerald—and what it taught him about the dangers of wealth. “As someone who grew up poor,” writes Rob, this story about money making a man unhappy “hit me like a bolt of lightning.”

Like most Americans, I read The Great Gatsby in high school and, as a restless kid growing up in foster care, it deeply resonated with me. F. Scott Fitzgerald’s 1925 classic captured the promise at the heart of the American dream: That your origins don’t have to define your future, that no matter who you are or where you started, you can make something of yourself. I understood Jay Gatsby’s desire for self-improvement and self-reinvention, his yearning to transform himself into something grander, to outrun his past and become something more. Something better.

I was born into poverty and grew up in foster homes in Los Angeles and the rural town of Red Bluff, California. I fled as soon as I could at the age of 17, enlisting in the military right after high school, then attending Yale on the GI Bill. I saw education, professional success, and wealth as tickets out—not just from poverty, but from every difficulty. I believed, like many Americans do, that you can self-improve your way into happiness, that enough success or enough money can solve anything.

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Rob Henderson
Rob Henderson is the bestselling author of "Troubled: A Memoir of Family, Foster Care, and Social Class." He holds a PhD in psychology from the University of Cambridge and is a Senior Fellow at the Manhattan Institute.
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