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Alumni in Action

Leading With Purpose

Business leader, activist, and MBA alumna Deanna Singh’s approach to achieving her goals

By Paul Smirl | Photography by Paul L. Newby II

February 26, 2019

Everything Deanna Singh does begins with a purpose: shift power to marginalized communities.

As CEO, author, entrepreneur, and nonprofit leader, Singh takes on many roles, traverses many sectors, and advocates in many different ways—all to embody her purpose.

Speaking to Wisconsin Evening and Executive MBA students as part of the M. Keith Weikel Leadership Speaker Series, Deanna Singh (MBA ’12) shared how following her purpose and finding solutions to problems led her to a career that truly impacts lives.

Speaker gestures while giving a presentation
Deanna Singh (MBA ’12) shares leadership insights with Wisconsin Evening and Executive MBA students. Photo by Paul L. Newby II

Following your purpose is not always a linear path

Singh compares her career path to a subway station: lots of movement, color, intersections, stops, and starts.

She has a B.A. from Fordham University, a juris doctorate from Georgetown, and a Wisconsin Executive MBA.

She brought the nonprofit LIFT to New York City to eradicate poverty, and in 20 years it has taken 100,000 families out of poverty for good.

She led the Milwaukee Street Law Project and gave high school students the opportunity to learn from law students and compete in a mock trial competition.

Singh’s managed millions of dollars as a business and nonprofit leader. She’s written two children’s books and just released her first business book, Purposeful Hustle.

Oh, by the way, she’s a doula, helping women experience ideal births for their children.

The four key qualities that help Singh achieve her purpose

Making an impact for marginalized communities hasn’t always been easy for Singh. She’s a naturally ambitious person, but fear, lack of experience in certain areas, and minimal resources have forced her to get creative and truly focus on her purpose.

Singh pointed to four key qualities to cultivate to be able to achieve your goals as they relate to your purpose.

You are going to fail. Embrace failure and say ‘hey, how you doin’?

Deanna Singh (MBA ’12)

1. Courage

Understanding the disparities that women of color and their babies face during childbirth, Singh saw an opportunity to be part of the solution. Being a doula wasn’t a natural role—she was scared of blood and joked in her talk about fearing routine cuts, but her courage and drive to follow her purpose took precedent.

She became a doula and started Birth Coach Milwaukee, an organization that uses its revenue to provide no-cost doula services to women who need them.

2. Curiosity

Less than 14% of children’s books feature characters of color. Singh wanted to change that and wrote a children’s book so young boys of color could see themselves in the books they read.

She knew little about being an author, publishing, or getting a book into market. Yet, the book, I Am a Boy of Color, was rooted in purpose.

She let her curiosity lead her to learning the skills and building the community to make the book a success.

“What do you do when you know nothing?” Singh asked.

Started with a letter to her two sons, Singh turned a passionate message into a book and a full-fledged campaign to get young boys and girls of color more books with subjects that looked like them.

3. Resiliency

“You are going to fail. Embrace failure and say ‘hey, how you doin’?’”

Instead of “failing fast” as some might say, Singh’s mentality is about making your missteps part of your mission. Singh embraces failure instead of seeing it as a roadblock, which has made her more resilient.

“I want to name my failure … I want to say, ‘look, I’m not really sure how it’s going to turn out, and I’m OK with that. Because I believe in this bigger thing we’re working at.’”

4. Initiative

Singh noted this one as the most challenging.

You don’t know where to start. You don’t have any time. You don’t have the money.

You need initiative.

Enter the 15-minute strategy.

Singh’s 15-minute strategy is simple. Devote 15 minutes a day to your purpose. Get to work 15 minutes early, close your office door, and work on the project you’ve been wanting to start. Do 15 minutes of research before bed. Find 15 minutes, build the habit, and invest in your purpose.

When Singh came up with a budget for I Am a Boy of Color, it totaled to $30,000. Having already written out her family’s budget for the year, it was clear that number was not going to work. She asked herself three questions.

What are things I don’t need? What are things I could teach myself? What are things other people are already doing?

Singh knew she was going to have to be scrappy and inventive to get a quality book into people’s hands. She taught herself about the writing and publishing worlds. She learned to build a website. She reached out to a former client to aid in the creative process, and she found an illustrator with whom to collaborate.

It all started by finding 15 minutes a day for Googling, making phone calls, and drawing up plans.

“The key ingredient is taking some initiative. It’s moving past where you are, where you’re comfortable, and saying ‘I want to be a part of the solution. I want to be at the root of the solution.’”

Deanna Singh speaking at Weikel Speaker event
Singh outlines her four key qualities for leading with purpose. Photo by Paul L. Newby II

Putting her purpose to work

Moving forward, Singh is continuing to work toward her purpose.

A portion of her children’s book sales go toward funding organizations that promote positive images of children of color.

Birth Coach Milwaukee is looking to expand.

She’s writing a book of fictional stories based on her experiences as a woman of color in leadership roles.

Her company Flying Elephant is spearheading an initiative for Wisconsin to be a hub for social enterprises—especially those with leaders from traditionally marginalized groups.

“Why are people not doing the thing that they think will have a big impact in their communities?” asked Singh.

“I literally reflect on this every day … Is this going to help me shift power to marginalized communities? If it’s not, I don’t have the time for it.”

The M. Keith Weikel Leadership Speaker Series at the Wisconsin School of Business enables Wisconsin MBA students to interact with and learn from accomplished business leaders and alumni. Executives from both the private and public sectors are invited to campus to address students.

The series was established in 2004 with a gift by John J. Oros (BBA ’71) and his wife, Anne Wackman. Today, the series continues as the M. Keith Weikel MBA Leadership Speaker Series thanks to a gift by M. Keith Weikel (Ph.D. ’66) and his wife, Barbara.