Finding Comfort in the Awkwardness 

A conversation about DEI and race

by Joanna C. de’Shay

The idea of having an uncomfortable conversation about race or racism is right up there with getting those wisdom teeth pulled that many people dread having done but know is essential to having and maintaining good oral health. No one likes or even wants to do it, but everyone knows that, at some point in life, they will have to be brave enough and strong enough to just get it done. What people are observing all around them today are those types of opportunities to bravely face the ugly and painful truth about the racism, unconscious bias and microaggressions that are prevalent in their communities, places of worship and workplace. 

What is essential is that people begin to talk about and, yes, in most cases, have awkward and uncomfortable conversations about Diversity, Equity and Inclusion and begin to unpack its insidious nature and the damaging effects that it has on the marginalized people of color it impacts. These conversations, although initially uncomfortable, can over time become easier and provide individuals with some brilliant moments to be transparent and honest with themselves about what they either didn’t know, couldn’t see or were just plain ignorant about. 

So, how does one do it? How does one begin to bravely forge into a conversation that could cause knots in their stomach and leave them feeling at a loss for the right words to say? The first step is simply to be open to having an uncomfortable conversation. Go into the dialogue with no preconceived notion of what to expect and refrain from becoming defensive or feeling attacked and, at all cost, relinquish the need to be right or feel heard. Just be in that exact moment, in that conversation, and listen intently with an outcome to learn. 

Those are by far some of the hardest conversations to have because they require a person to be vulnerable and trustworthy and demonstrate that they have good intentions to want to understand a person of color’s lived experiences. 

Then, one must begin by being realistic about where to start on this journey, how to keep the conversation moving forward organically, and how to “check-in” to ensure mutual feelings of communal movement, exchange, and growth. Often, people seem to compare their journey to others — but the reality is, no one person sees race or racism through the same pair of rose-colored lenses. It all depends on how a person was raised or what he may have been exposed to later in life or maybe even a traumatic event that has left conscious biases or wounds. It’s all a continuum of learning, and everyone has to be comfortable with their own awkward starting point. 

Being honest about feeling awkward can also be empowering and, over time, will allow people to have these transformative conversations even if they feel uncomfortable initially. As the wonderful and late Ruth Bader Ginsburg so famously stated, “Speak your mind, even if your voice shakes.” That truth, as uncertain and scary as it seems, is the soul healing we need to begin to see each other’s wounds and find a way to heal them, together — and that starts by talking. 

The time for that reckoning is now, as it is imperative that as a nation we learn to dismantle the barriers that perpetuate a hateful and divisive system of us-versus-them. Once a person decides to commit to the journey of anti-racism, she can then begin the cathartic journey of cultural humility, placing the person, the human, squarely at the center and connecting to all the wonderful characteristics that they bring, such as their race, ethnicity, culture, gender, religion and sexual orientation. In this space, one can begin to receive and honor a variety of perspectives, which eventually leads to finding greater comfort in the awkward state of starting, engaging in and even taking a deeper dive into dialogues around more controversial topics, such as white fragility or even privilege. It is about transformational change and, like everything else in life that is worth having, it takes time and effort and requires a greater level of intentionality and commitment. 

This is the mark that some companies miss when approaching DEI work; they forget that DEI work is heart and soul work and requires a long- and short-term strategy that demonstrates both intention and commitment in small, tangible ways but also in big, demonstrative ways. Nothing should be “off the table” if done genuinely and authentically with intentionality. Proactive Inclusion is what companies should strive for daily, where their intention is measured by how they choose to amplify the voices, experiences and perspectives of marginalized people, groups and even ideologies. 

It’s time to find comfort in the awkwardness because the silence is breeding ignorance — and that ignorance like a virus is spreading, causing chaos, hatred and division. 

Joanna C. de’Shay is the executive director of Diversity Leadership Alliance. The epitome of a disruptor who designed an intentional life filled with success on her terms, de’Shay is a change agent who left a corporate career of more than 15 years to start her own clothing label and serve her community. 

Read the other articles that are part of this “Diversity, Equity and Inclusion: The Time Is Now” cover story.

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