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‘Deconstructing Karen’ Documentary Challenges White Women To Stop Being ‘Nice’ And Start Getting Real About Antiracism


There’s a grand paradox about racism. Virtually everyone agrees that racism still rages on, yet virtually no one admits their own racism. Indeed, it seems that our workplaces and broader society are both caught in the grips of an “everyone else is the problem” mentality.

The groundbreaking new Apple iTunes documentary Deconstructing Karen explores the Race2Dinner concept led by founders Regina Jackson and Saira Rao. During these dinners, Jackson and Rao facilitate radically honest conversations about race with eight white women at a host’s home. In the documentary, Rao begins one such dinner with a simple, chatter-stopping, smile-freezing buzz-kill of a request.

“So, I want a show of hands of everyone at this table who is racist.”

Predictably—and some might argue understandably—a deafening silence drops like a thud. After all, while racism is in fact as American as cherry pie, virtually no one associates themselves with the label ‘racist’—at least not without a lot of snarky defensiveness, indignation or even tears. Fortunately, pushing through that predictable, visceral individual defense system is Jackson and Rao’s specialty, and in some ways, their goal.

Jackson and Rao’s unapologetic, determined, persistent approach seems radically different for very good reason—it is.

In the aftermath of the summer 2020 racial reckoning many “progressive” white people have engaged in these conversations—about racism, anti-racism, being non-racist vs. antiracist, inclusion vs. diversity, equity vs. equality—like never before, yet those conversations have virtually all been conducted within the suffocating confines of three unwritten rules that tend to dominate our workplaces and broader society.

Rule #1 – Willingness to participate in conversations about racism proves that you’re a “nice person.”

Rule #2 – Being deemed a “nice person” is more important than actually tackling racism and achieving more equitable outcomes.

Rule #3 – Anyone willing to participate in conversations about racism should not be made to feel uncomfortable or anxious because….well, see rule #1.

Instead of mindlessly acquiescing to these ego-centric, status quo-protective rules, Rao and Jackson instead have only one rule for their dinners—no crying in the room. Why? “Even in a group of women, the woman crying centers herself and deflects from any conversations, learnings, or knowledge being shared,” co-author and co-host Regina Jackson explains. “If a white woman wants to stop any conversation, especially those that are uncomfortable for themselves, they know to cry.”

Indeed, Rao and Jackson are insistent on cutting through the noise and theatrics that too often take center stage because they see these dinners as a unique way to begin to confront racism head on. “The only thing that’s going to change this is if we change the cultural DNA and the only way you can change the cultural DNA is through personal human interactions, and we know that breaking bread with people is the best way to do that,” Rao insists.

Easily misunderstood and misrepresented, these Race2Dinner conversations are radical in their defiance of these tacit constraints that continuously prioritize comfort over progress. For those quick to paint this philosophy or approach as misguided or “aggressive,” it’s important to acknowledge that it’s really not radical or new. Perhaps the most famous advocate of such an approach was Dr. Martin Luther King himself who in his famous Letter from Birmingham Jail railed against the white moderate insisting, “I have almost reached the regrettable conclusion that the Negro’s great stumbling block in the stride toward freedom is not the White Citizens Councillor or the Ku Klux Klanner but the white moderate who is more devoted to order than to justice; who prefers a negative peace which is the absence of tension to a positive peace which is the presence of justice; who constantly says, ‘I agree with you in the goal you seek, but I can’t agree with your methods of direct action…’”

In their recent The New York Times bestseller White Women: Everything You Already Know About Your Own Racism and How To Do Better, Jackson and Rao are clearly more interested in confronting and challenging the subtle yet devastating ways that racism shows up than soothing, coaxing and coddling individual egos. During the awkward dinner depicted in the documentary, they regularly call out attendees for playing victim, centering themselves and selfishly siphoning attention and energy away from productive, critically needed discussions of the realities of systemic racism. Their antiracism religion seems to be an intervention-style tough love that’s both confrontational and necessary.

Rao and Jackson’s work challenges white women to stop seeking rewards for being nice and instead actually speak up and take action in their workplaces and beyond. “So the next time you think things like,I didn’t pipe up on Facebook because I don’t want to be attacked,’ or ‘I’m scared I’m going to say the wrong thing,’ orThe last time I called someone out at a dinner party, my husband was grumpy with me for a week,’ think about this: The only wrong move is remaining silent, sitting on the sidelines, accepting your role in white supremacy. Don’t do nothing out of the fear of doing it imperfectly,” Rao explains in her TIME article “White Women Must Do More to Confront Racism.”

The dinner closes with Rao returning to the initial request for a show of hands of those who consider themselves racist, and this time hands quickly shoot up. Admittedly, some may be doing it as a performative “let me outta here” gesture, but perhaps some have shifted their perspective and can now connect with their participation in racism. Some may not have changed their perspective fully but may be motivated enough to lean into discussions about race with less defensiveness and more curiosity. Perhaps for someone at the table the experience lit a fire in them that will propel them to become an intrinsically motivated lifelong warrior against racism. Clearly, the ultimate goal is for newly enlightened white women to spread that racism consciousness and advocacy like an airborne contagion wherever they go. Without question, that goal, if achieved, would have accomplished more than most traditional corporate DEI trainings ever could.

Arguably, the stagnation of workplace anti-racism efforts—notoriously long on intention but short on impact—suggests that perhaps workplaces need an intervention, a radically different approach. While conversations are an important and necessary step, all conversations aren’t in fact built the same, and some can in fact be counterproductive yielding adverse impacts. Perhaps organizations truly committed to antiracism would be better served by moving away from low value, performative, conversations (whose only real goal seems to be getting credit for having had a conversation) toward higher value conversations that decenter individual feelings and challenge and fortify racial stamina while enabling incremental shifts in organizational culture and business outcomes.

Indeed, perhaps it’s foolish to expect radically different results unless we’re first ready to have radically different conversations.



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