Wake Up Cape Cod

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A Comfortable Uncomfortable Conversation About Race

Ever since the senseless, tragic murder of George Floyd at the hands of police officers on May 25, 2020, we've wanted to have a comfortable uncomfortable conversation about race.

We have to come together to talk openly and honestly about a topic that many of us may have never brought up with people before.

While we could have met online using Zoom or another social media platform, we knew this conversation needed to be held face-to-face, away from a computer screen.

So we invited our friends Jonathan "JT" Thompson and Peter Winfield to meet us at the Barnstable Brewing Company in Hyannis. JT is a motivational speaker and the creator of JT's Chronicles, a vlog concentrating on positivity and community. Peter Winfield is a longtime media sales and marketing executive.

Together, we'll tackle the questions we're uncomfortable asking, but we need to discuss.

Pictured: Kevin Matthews, Nina Jackson, Jonathan Thompson, and Peter Winfield

"This is something I've dealt with since I was a child," Winfield shares, speaking of living with racism.

"I'm getting ready to go to school one day and there was a test... and I was probably no more than 9 or 10 years old. And the first thing my mother said to me when I was leaving the door, she says, 'You have to do better than everybody else to get the award. The white kids are going to get the award first even if everything is equal.' She said, 'You have to be better.'"

Winfield laments the burden of carrying that lesson his entire life. "I'm not going to be treated equally."

"When you're an African American, you live with this all your life."

Where does this mentality come from? Why does racism exist? Kevin posits that there are two factors integrated into the core of racism.

"Racism is based on two things: fear and ignorance."

"None of us are born to be racist," Kevin continues. "It's taught."

"It's learned," Winfield confirms.

In overcoming this learned behavior, JT acknowledges the importance of recognizing our differences, and the danger of claiming to be "colorblind."

"Don't say, 'I don't see color,'" JT explains. "I need you to see me. I am what I am, you are what you are."

As a black woman, Nina feels pressure to excel in order to overcome people's preconceived notions based on her skin.

"Sometimes I feel like I have to work a little bit harder than everybody else. Or I have to present myself a little bit better or nicer... for people to see past that I'm black."

Location is also a factor.

According to Nina, her skin drew notable attention when she was a child, summering in Swansea.

"I'm originally from New York, so when I moved," Nina recalls, "the only black people I knew were my family. My grandfather was the darkest person in our town."

"So when I went to stores, it was like, 'oh, there's a little black girl.' I was the only little black girl ever."

Listen to our entire comfortable uncomfortable conversation below.

Have an uncomfortable question about race that you'd like us to talk about? Email Nina with the subject "Uncomfortable Question."


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