W. Kamau Bell On Why Awkward Conversations Will Change Your Life

Comedian, author and host of “United Shades of America,” W. Kamau Bell, on how awkward conversations make you a better person and the world a better place.

W. Kamau Bell On Why Awkward Conversations Will Change Your Life

Perhaps nobody should talk to noted white nationalist, Richard Spencer, he of the face-punch heard ‘round the world. If someone does have to speak with Spencer, however, and on TV at that, it’s for the best that it’s W. Kamau Bell. After all, Bell is such a virtuoso of the awkward conversation that if he doesn’t change Spencer’s mind—and let’s face it, he probably won’t—he’ll at least extract some valuable nugget of insight from hearing him out, and share it with the rest of us.


W. Kamau Bell [Photo: John Nowak/ courtesy of CNN]
The word awkward used to mean something else. Before it came to be embodied by Zooey Deschanel’s adorable social ineptitude, or Larry David’s curmudgeonliness, it was something grittier. When W. Kamau Bell has an awkward moment, it’s more productively uncomfortable than, say, failing to acknowledge a fair weather acquaintance at a party. Historically, the veteran comedian with a political bent has used awkward conversations to break down barriers and find out who people really are–and what they need him to be.

“This country gets better when we confront things we feel awkward about,” Bell says. “The seed of every protest is someone going ‘Hey can I talk to you about something that’s not working for me?'”

Productively uncomfortable conversations are a specialty Bell serves up on his Emmy-nominated CNN show, United Shades of America. They’re something he also does on his podcast, Politically Re-Active, alongside co-host Hari Kondabolu. And these types of talks are particularly abundant in the pages of his just-released book of essays, The Awkward Thoughts of W. Kamau Bell. Although Bell began writing the book long before November of 2016, it became a much more timely work following the election, when many people woke up to the fact that they don’t know their neighbors as well as they thought.

“This is like The Matrix but less fun,” Bell says, laughing. “We didn’t all learn kung fu.”

Although the book veers between straight-up memoir and trenchant essays about the issues currently dividing our nation–along with black superheroes and other illuminating diversions–one constant is awkward conversations. It’s clear from the book that Bell has learned a lot from wading through the muck of discomfort separating cultures, political beliefs, races, genders, and sexual orientations. Fast Company spoke with the comedian and author recently to find out more about how and why having these conversations can change a person’s life.


 Buy Lunch For Someone Who’s Nothing Like You

Everybody resides in some kind of bubble, geography be damned. The only way to pop yours is by meeting different kinds of people and finding out what they know that you don’t. The only problem is, it doesn’t just happen automatically.

“I think a lot of times people think like, ‘I asked that black guy at work, who I never talk to, to explain Black Lives Matter to me and he looked me like I was crazy,'” Bell says. “There are people around you every day who you don’t talk to enough. The way to get to these awkward conversations is to first form friendships. So instead of not talking to that guy at work, actually have a conversation. You don’t start on the first day going ‘Tell me about your deepest, darkest secrets.’ You start with ‘Let’s go out to lunch.’ Buying somebody lunch will go a long way to them one day divulging their deepest, darkest secrets. At some point, you can with your good friends go ‘Can you explain BLM to me?’”

Allow People To Explain What New Words You Should Use

The more you talk with people who don’t look or think exactly like you and share your confirmation bias, the more you’ll bump up against our hyper-evolving language. That’s where things get interesting.

Politically Reactive

“There’s a tendency in many of us, when somebody says there’s a new thing called cisgender, we’re like ‘What? Another new thing? I can’t learn another new thing!’” Bell says. “But if you’re friends with somebody who knows about that thing, they’ll explain it. Like when [comedian and TV host] Guy [Branum] explained cisgender to me the first nine times, I was like ‘I still don’t think I get it.’ But since this is my friend, Guy, I know he wants the best for me, so I’m not doing myself a service by not leaning into this office.”


Allow People To Explain What Old Words You Should Not Use

It’s difficult to consciously change the way you’re used to speaking–unless, that is, you listen to and ask questions about somebody’s case for doing so.

“If you want to live a life where you can use whatever words you want and it doesn’t seem to be hurting you in any way, go for it. I’m not gonna get into a free speech argument, but for me, it’s very clear,” Bell says. “Like with my friend, Martha Rynberg, and the word ‘bitch.’ She kept explaining why I should stop saying it, and I resisted. But eventually, I knew this was gonna be a thing that might lose me this friendship. Or at least it would alter this friendship from the thing I want it to be. At a certain point, you gotta ask: If you’re using the words you want, are you leading the life you want to be leading?”

Shame Is Your Friend

Awkward conversations about gender, race, sexual orientation, and politics are not always going to be fun. That’s why they’re awkward. Sometimes you’re just going to have to get your ass verbally kicked.

“It’s a little like those massages that scrub all your dead skin off. Sometimes people aren’t prepared to give you a spoonful of sugar as they give you the medicine, just because they’re not in that space, and you have to be okay with that,” Bell says. “Some people are always gonna say ‘But I just feel so much shame.’ Okay! What’s wrong with shame? The problem with any one emotion is if you stay in it for too long. Shame is fine if you use it as a motivator to move onto something else. Shame has turned me into a better person many times. I’m a much better husband because of shame. I’ve improved a lot as a result of some ‘My God, I can’t believe I screwed that up!’ moments.”

The Awkward Thoughts of W. Kamau Bell: Tales of a 6′ 4″, African American, Heterosexual, Cisgender, Left-Leaning, Asthmatic, Black and Proud Blerd, Mama’s Boy, Dad, and Stand-Up Comedian

But Don’t Go Around Apologizing

Sometimes, people think they’re having a necessary awkward conversation by apologizing to someone else, unprompted, on behalf of their race or gender. They are not entirely correct.


“To quote Daniel Tiger, ‘Saying I’m sorry is the first step to how can I help,’” Bell says, laughing. “A lot of times people think the apology is the thing, but the apology is definitely not the thing. It’s like, ‘I’m sorry on behalf of all white guys.’ Okay. Now, what can you do to help make sure that the thing you’re apologizing for doesn’t happen again? And a lot of times people don’t even want to get caught up in that; they just wanna go, ‘I said I was sorry.’ When a kid goes ‘I said I was sorry!’ you go, ‘That doesn’t matter. What are you gonna do?’”

If It’s Too Awkward, Keep Going . . . Later

The thing about awkward conversations is that sometimes they end in an even more awkward place than they started. All that outcome means, however, is that there is much more to discuss next time.

“You can get caught into dead ends in these conversations. You can get caught in a place where you’re not going to resolve this point right now or agree on anything. But I think just thinking that every conversation has to end up in a solution is the problem,” Bell says. “These are a series of conversations you have to have with people. I hear from people all the time, like ‘I tried to talk to my grandfather and he wouldn’t listen.’ Once? You tried to talk once? That’s the problem is we expect too much from each individual conversation, and if you expect too much too soon, you’re not really understanding how this works. Sometimes, the conversation has to end with, ‘Okay, I need to sit with that for a minute.’ Some things, I’ve had to sit with and struggle with and come back to. And when that’s happened, it’s always been for the best.”