Although Deanna Singh spends her days advocating for others, one of her most vivid memories of Girl Scouts was a day that she had to advocate for herself.
Her Southeastern Wisconsin Brownie troop was creating crafts as presents for Mother’s Day, and her troop leader wanted to cut a little lock of her hair to attach to a poem as a gift.
“I’m biracial,” explains Deanna. “My mom is African American and my Dad is Sikh, and in the Sikh culture, we don’t cut our hair. But I was in kindergarten or first grade, and I didn’t have the words to explain it.”
“When my mom came to pick me up, I was running around in a circle, and all the women [troop leaders] were chasing me!” she recalls.
Once Deanna’s mother explained that her daughter’s insistence on not participating in that part of the craft was for religious reasons, the adults were receptive and understood where the misunderstanding happened.
“But it was a moment of leadership for me,” Deanna explains, “because . . . I ran!”
As an adult, Deanna has worked to shift power to marginalized communities from a variety of positions—as a lawyer, a middle school principal, and the CEO of multiple foundations.
And she’s always drawn attention for her work; she’s been recognized by the Milwaukee Business Journal as one of the most influential “40 under 40” leaders in the community and by the University of Wisconsin’s School of Business as one of “8 Under 40” leaders to watch.
Four years ago, she left her last job to write Purposeful Hustle: Direct Your Life’s Work Towards Making a Positive Impact (Bookbaby, 2018). The book’s goal is to help readers uncover their own purpose and determine what to do with it.
After she finished writing the book, she decided to lean into her entrepreneurial instincts. Within a year, she had launched three new businesses.
“I have three companies that fit under Flying Elephant; it’s an umbrella org for three social enterprises. Uplifting Impact provides coaching and training around leadership, DEI [diversity, equity, and inclusion], and entrepreneurship. I have a children’s book imprint called “Stories to Tell” books that publishes books that have positive images of people of color. And Birth Coach Milwaukee provides doulas for coaching before, during, and after birth,” she explains. “We’re trying to eliminate the disparities for women of color in labor.”
When asked if launching three companies felt like a lot to take on in a short period of time, she laughs.
“I’ve always had some sort of entrepreneurial venture,” Deanna says. “Start-up is the space I feel most comfortable in.”
She’s also most engaged when she’s helping people who have been pushed to the margins—whether that’s women, people of color, children, or senior citizens.
“I’m the type of person, if I see something I don’t like and I am not satisfied with the solution," she says, "I am going to do something about it.”
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