The Coolest Black Family in America, No. 43:<br />
The Baileys

Meet the Baileys

Demonstrative love wasn’t always present in Diane Bailey’s household growing up in Brooklyn. Her parents, who separated when she was 3, were never really affectionate with one another. Although she was well taken care of, Diane explains that her mother was more focused with raising her to be strong and independent than showering her with kisses and hugs.

“As a kid, I fell down and busted both my knees,” recalls Diane, who thanks her mom for grooming her into the strong woman she is today. “My mother, who was a nurse at the time, bandaged me up and told me I was fine. There was no ‘let me make it better.’ ” Diane’s mother raised her a daughter alone while building a successful natural hair salon (Tendrils) from the ground up, establishing herself as an innovator in the natural hair industry.

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Despite her many accomplishments, Diane admits the lack of expressive love between her and her mother growing up (“Today, she is always telling me she loves me”) left her with a fear of intimacy.

“A girlfriend of mine was emotionally hurting, and she was crying. She went to grab me to embrace her, and I just pulled back. She told me how bad I made her feel and how hurt she was. That was my instinctive reaction, but that’s not how I felt at the moment. I wanted to hold her, but I did not allow myself to do that,” Diane clarifies. “She made me promise that when I had a child, I would show her love and never pull away.” Showing affection to her friends may still require a conscious effort on her part. But when it comes to her daughter, Kai Jackman, Diane has always been expressive with her love.

In fact, as a single mother, Diane felt she had to shower her daughter with boundless love to compensate for the lack of fatherly attention. She’s been overprotective of her daughter to a fault, she admits. Like the time Kai was scared to go to the basketball courts because a girl wanted to fight her. Diane marched down to the courts with boxes of pizzas in hand for everyone, thus halting the ensuing dispute.

Diane fought to make sure Kai had access to the services she needed to succeed in high school. Soft-spoken, 23-year-old Kai struggles with an auditory processing delay. Since she was young, she’s had difficulty understanding, storing and retrieving information. While Kai may have had some challenges in high school, she graduated on time and never repeated a grade. When Kai moved to Florida two years ago to attend college, school has been a struggle without her mother’s guidance.

Coolest Black Family, No. 43: The Baileys

The Coolest Black Family in America, No. 43:
The Baileys

“It’s definitely been a challenge having to be on your own and take on more responsibilities,” says Kai. “I don’t think school is for me, but I know it’s important and I want to try harder. I didn’t think I could graduate from high school and I did.” Kai acknowledges she needs to make school even more of a priority.

“I advocated for her on so many levels that there were times I should have allowed her to advocate for herself,” Diane points out. “Now it’s time for her to speak up and she’s having issues. Did she go to school and explain that she needed special help? No. Therein lies the problem. Now that she has to do it, she doesn’t want to because she is afraid or doesn’t know how. I was always doing it for her.”

Taking a backseat and letting Kai take on a more proactive role in her own life hasn’t been easy. But Diane recognizes the importance of allowing Kai fall and skin her knees as she did as a child. “It’s a huge change for me. Before I would run to her rescue and it would be ‘poor Kai.’ She is getting it now and coming around,” says Diane, who gives Kai assignments over the summer in hopes of improving her reading and writing skills. First up, Kai had to write a letter detailing where she saw herself in four years. “It was eye-opening to write. It really made me think about my future and what I need to do to reach my goals,” says Kai.

Following in her mother’s entrepreneurial footsteps, Kai has dreams of opening a nightclub. “I know I need to finish school and earn my degree to make it happen,” says Kai. Diane was in her twenties when she opened her salon back in 1987. “There is no shortcut to success. I want her to know it’s a journey and not something that happens overnight,” says Diane.

Diane’s infatuation with styling hair developed early on as an only child. To entertain herself, a 7-year-old Diane cut off her hair and braided it back. “I knew it was a passion very early,” she says. While in college, she enrolled in school to be a licensed makeup artist. All through the first couple of years of college, Diane worked as makeup artist at Bloomingdale’s.

“I started doing hair when this woman showed me how to put extensions, and once I did my own hair, everyone would ask me to do theirs,” says Diane. After getting fired from Bloomingdale’s, Diane printed up some business cards and started freelancing as a hair stylist for five years. It quickly became apparent that her skills were in high demand, so she went back to school to take some business classes with plans to open Tendrils. “I developed a business plan and got an A in the class. My professor told me it was a viable plan,” says Diane.

Tendrils launched as a “comprehensive braiding salon.” In 1990, three years after Tendrils opened its doors, Diane made a fateful decision to stop working with chemicals in her salon, in hopes of demonstrating to Black women how beautiful their natural hair could be. “The smell of opening a bottle of relaxer would gag me out so much my stomach would get queasy,” declares Diane.

She went from styling ubiquitous braids to pioneering natural styles that are now in vogue, like locs, natural weaves and Afro extensions, back in the late ’80s. Her trendsetting vision made her a natural hair expert. “In 1991, a magazine sent me four models to do their hair, and I sent them back 10 with all types of natural hair styles. Things just blew up from there,” she recalls.

Her personal hair journey to natural hair was life changing. Diane wore her hair in many styles, from jheri curls to braids, until she found the confidence to go natural. “I believed like many Black women that I needed long straight hair or I wasn’t good enough. I grew up with those same insecurities. I thought my nose and my lips were too big. I never saw myself as pretty,” Diane reveals. When she turned 30, all her self-doubt instantly vanished.

“I just woke up one morning and it was like an epiphany. I just felt whole and full and I got the courage to get rid of the braids I wore for nine years,” says Diane. She started wearing an Afro and later opted for locs. “When I got my locs, I thought I was an African goddess,” Diane says, chuckling. “I started wanting to buy nice clothes, take better care of myself and eating better. I was so pleased with myself and it was the best thing ever.”

For her one-year celebration of opening Tendrils, Diane threw a party… and that’s where she meet Kai’s father. They dated for two years and were married for almost three. The union didn’t last long, due in part to her ex-husband’s unwillingness to put in the work needed to build a healthy marriage. “I asked him, ‘why did you marry me?’ He said he just wanted to see if he could. It was so hurtful and horrible. I waited until I was 35 to get married and I thought I picked the right man, but I picked a selfish man. He was a narcissist,” explains Diane.

By the time Kai was a year-and-a-half, her father was out of the picture.

“My dad hasn’t been really involved in my life. She’s my best friend,” says Kia. “It really hurts that all this time I’ve been in Florida, he hasn’t come to see me. My mother did everything for me and she’s all I got.”

Juggling raising a daughter, running a business, writing a book and working on photo shoots was so stressful for Diane that her health suffered. Her hair started falling out and she had insomnia. “I have highs and lows,” she says. “When you don’t have back up, nothing can go wrong with you. Suppose something happened, who is going to pay the mortgage? I had nobody to help me. The worries just snowballed into what ifs and more what ifs.”

She turned to acupuncture, therapy, yoga and meditation to help combat her anxiety over the years. Still, it wasn’t until she closed Tendrils in 2012 that