Op-ed: We need to stop the ‘privilege of stupidity’ among leaders

Picture this: You’re at an award gala for a project you and your team spent over a thousand hours working on. It went through revisions, blood, sweat, and tears, and finally garnered an award nomination. So when the winning team (not yours) accepts the award and says something like: “We don’t even know how this happened! We’re kinda dumb?” you would be forgiven for flipping a table.

Was that hard to picture? Or was it your lived reality of working in business? Maybe you didn’t witness this at an awards gala. Maybe it was in a boardroom, a Zoom call, or even a Slack message. I didn’t even tell you to picture the winning team, but you may have had an idea, right?

It’s an infuriating phenomenon for people of color, queer folks, and women who could never stand on stage and say “I don’t deserve to be here” and shrug, telling the tale of their success like a standup comedy routine, without serious backlash. Especially at a time when DEI initiatives are under fire and affirmative action has been all but erased.

Quite frankly, it’s a privilege to act stupid without fear of repercussions.

“Stupid” sounds harsh, but it needs to. The acceptance of this lackluster character trait for business leaders is harsh for those of us on the other side of the demographic coin. So let’s look at the privilege of stupidity: where it comes from, how it plays out, and what we can do about it.

What is the ‘privilege of stupidity’?

It started, as with many questionable workplace trends (mandatory beer pong, anyone?) in Silicon Valley. Tech amplified the myth of meritocracy in the workplace, lauding ideas that anyone could be successful or become a unicorn company if they worked hard enough and wore enough American Apparel hoodies. Suddenly, dropping out of college, a là Steve Jobs and Mark Zuckerberg, was the new Ivy League degree. Under it all, these leaders weren’t “better than anyone else”—they were relatable.

To be seen as “relatable” and “casual” in the workplace, to showcase your own shortcomings, or even to play stupid to get others to do your work (a whole other conversation), is a privilege. Of course, we’ve seen time and again, this has its limits. But while Silicon Valley has had more of a reckoning with questionable leadership, many of the same leaders are still out in the world receiving funding and trying again. Meanwhile, many others aren’t even given a first chance.

Why this is harmful

According to research, men start new businesses at a rate 64% higher than women and white people start new businesses at a 22% higher rate than Black people. These numbers don’t just fall from the sky; they illustrate what we know: It’s much harder for women and people of color to gain access to the social and financial capital to start businesses. And if you’re a double minority (a woman of color or a queer person of color), it’s doubly difficult.

You’ve probably heard the phrase “working twice as hard to achieve half as much.” But working twice as hard isn’t even just for us, as individuals, it’s for us as a community. If we fail, it will take much longer for other Black people, other women, other LGBTQ+ founders, or anybody who isn’t a white man, to get that chance or opportunity again. Our successes and failures are connected to an intricate tapestry of others and us. And that weight that we all carry for one another is heavy.

Consider the startup world, where the notion of “fail fast, fail often” is almost exclusively applied to white male entrepreneurs. Their ventures receive significant funding and support despite a track record of poor decision-making. Look at Justin Caldeck, an investor who resigned after six women accused him of unwanted sexual advances, who is right back to investing. He even received such softball coverage on Maxim. Or Adam Neumann of WeWork, who failed spectacularly in his goals, but was given a golden parachute and even recently tried to buy back the company. Behind every blunder of this group of founders, there’s a safety net made of privilege.

In contrast, women—particularly women of color—face a drastically different reality, one where failure often results in the end of our entrepreneurial dreams rather than a stepping stone on the path to greatness. Intersectionality plays a major role here. It’s why businesses can identify as Black-owned, women-owned, or queer-owned. The playing field is so uneven that businesses not run by white men need to be amplified to get in the game. While the aforementioned tech leaders may still have access to their network and resources, venture funding for Black-owned startups has fallen as much as 79% in 2023.

I also want to note that when I say “privilege,” I don’t mean that these leaders have had it easy or didn’t work hard. We know they did. That’s half the point. The privilege here is that none of the challenges these leaders have faced have been due to inherent characteristics like the color of their skin, gender, or sexual orientation. So when they stand up and point out that they had it easy and it’s played for laughs, it’s insulting.

In reality, working twice as hard is the bare minimum. When your existence checks multiple “diversity” boxes, you have to damn near work through an algebraic equation to get close, but still not equal. That’s why the “shrug emoji” acceptance speech, internal message, or Tweet is so infuriating.

How we can do better

This is not just about punching up to white men or singling out a few high-profile figures. It’s about a broader system that allows certain people to make mistakes, feign ignorance, and still land on their feet (if not be lauded for it). Meanwhile, the rest of us not only face the consequences of our errors with a much harsher reality, remembering and revering every step we took to get where we deserve to be.

Business leaders need to be accountable. If not for themselves and their companies, for their teams, communities, and industries. Do not stand on stage and say you didn’t work for your award. Do not relay your rise to stardom as a comedy of errors. Take your flowers without diminishing the experiences of those around you, and when you’re at the top, reach back and help those who might not have had your (multiple) opportunities for success.

Let’s work toward a business landscape where everyone, regardless of their background, has the same chances to succeed—or fail—without the safety net of privilege.