For years, wise and successful women have been urging their sisters not to be afraid of their own ambition—to be strong, to take control, to “lean in,” as Facebook exec Sheryl Sandberg famously put it in her eponymous 2013 best-seller. (As perhaps the wisest woman of all once said: “I’m not bossy—I’m the boss.”)
Yet in practice, it’s not always easy to follow the advice of these strong, confident, famous women—especially if you’re, say, an anxious millennial who’s been socialized to care far too much about what other people think of you. Perhaps nobody knows that better than the multi-talented Rachel Bloom, who’s spent two seasons expertly skewering gender and social norms on the CW network’s Crazy Ex Girlfriend. (The Golden Globe-winning musical series is a lot funnier than we’re making it sound.)
So when Vanity Fair asked Bloom to make a video in honor of our very first Founders Fair—a conference celebrating female entrepreneurs—she really leaned in, composing an ode to the confusing conundrum of being both a leader and a woman at the same time. The song starts out as a standard empowerment anthem, before, like most of Bloom’s work, it takes a swift left turn:
“Ladyboss”—sorry, that’s “#Ladyboss”—can’t answer that question, or the immortal quandary of what, exactly, an empowered woman should wear to work. (Read: “How much boob is too much boob? How much boob is too much boob?!”) But it does pose those queries in an exceptionally catchy way, and presents at least one conclusion: that no matter how confusing it is to be a woman at the top of the food chain, nobody cares what Derrick has to say about that.
V.F.’s Founders Fair will be held April 20 in New York City.
