The recent New York Times expose on the Trump family—and how Donald’s father passed along hundreds of millions of dollars to his son—has once again exposed the way great wealth is often the result not of hard work and talent, but inheritance and intergenerational handouts. Although the focus of the story was on the Trumps, its value goes well beyond piercing the veil of self-dealing and occasional graft at the heart of one family’s empire. The narrative of “rugged individualism” and the myth of meritocracy—the idea that people “make it” or don’t based on talent and hard work—is firmly ingrained in the American psyche. Exposing the falsity of the notion as it regards the Trumps can allow us to examine the broader concept as it regards the rest of us and the society we share. In this extended commentary, I explore the reasons why the notion of meritocracy is so compelling, psychologically, even for folks who are struggling. I also examine the evidence suggesting the notion is more mythical than real, and then delve into why the mythology is actually dangerous for most Americans, both individually and in terms of the kind of society people beholden to the concept end up creating. Finally, I offer a method for progressives to push back against the notion of meritocracy and individualism, which can begin to chip away at this key stumbling block to solidarity: namely, a radical and transparent humility about our own stories. By acknowledging our own path—the unearned advantages we had, perhaps because of economic status or racial privilege, or even the luck and serendipity over which we had little control—we can forge an honesty that makes it harder to judge those below us and less likely that we’ll undeservedly praise those above. And by sharing our stories with others, we can build sustainable movements rooted in humility and a sense of collective purpose, both of which are critical to the creation of a more just society.