Deanna Singh


Deanna Singh is a highly respected thought leader who travels the world motivating and educating audiences about living with joy and purpose. A gifted communicator, she is a champion for marginalized communities and an inspiration to all those who want to be agents of change in their work, lives, and society.

Singh earned her Bachelor of Arts in Urban Studies from Fordham University, a Juris Doctorate from Georgetown University, a Master’s in Business Administration from the University of Wisconsin, Madison, and certification in Diversity, Equity, and Inclusion from Cornell University. She has impacted the world as a speaker, a teacher, a principal, a leader of large foundations, a social entrepreneur, a businesswoman, an author, a publisher, and a mother.

Because of her creativity, tenacity, and change-provoking honesty, Deanna Singh is in demand as a motivational speaker and educator for teams from a wide variety of organizations. She is regarded as an expert in leadership; entrepreneurship; and diversity, equity & inclusion and speaks frequently to corporate, university, and association groups on all three topics. She also visits schools to share her experiences and her three children’s books, I am a Boy of Color, I am a Girl of Color, and Cloth Crown.

Singh has been recognized by the Milwaukee Business Journal as one of the community’s most influential 40 under 40 leaders and the 8 Under 40 to Watch for the University of Wisconsin School of Business. She is also the recipient of the United Way’s Philanthropic Five Award and the Wisconsin Department of Public Instruction Leadership Development Hero Award.  She also sits on the national board of LIFT.

Singh has also spent more than two decades researching, designing, and building asset-based solutions to complex social challenges while raising awareness for underserved populations. She created Flying Elephant, a social venture umbrella organization that consists of three unique enterprises. The first is Purposeful Hustle, where we help people make a positive impact in the world through leadership development.  The second is Uplifting Impact, a consulting firm focused on helping leaders and organizations create innovation through inclusion.  Next is her children’s book imprint Story to Tell Books, which impacts children of all colors. Last, there is Birth Coach Milwaukee, an organization that provides doula services to women and works to eliminate the disparities in birth outcomes.

Deanna Singh’s fully customizable, interactive, and authentic sessions have received accolades from clients and participants from all walks of life. Her courage, positivity, and boundless imagination pervades the stories she tells, leaving audiences with an understanding that with the dawn of each new day, they can choose to have a positive impact on the world.

"Passion is often masked as a luxury when it is really an essential ingredient in life."
-Deanna Singh

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Deanna offered a remarkable Keynote to kickoff our AmeriCorps members' term of service. Her genuine warmth and excitement was absolutely motivational and truly set the stage. We continue to get stories and appreciation for her amazing presentation. We are so grateful to have shared a powerfully inspiring moment of growth with such a tremendous change agent!

Amy Porter, Event Planner


Deanna is an artful, honest storyteller. She weaves her stories into messages filled with wisdom and delivers those messages in ways that touch the heart and soul. Those who listen to her walk away with a greater awareness of their individual power and a greater confidence that they can translate that "power" into a substantive and meaningful change in their communities.

Christine Hill, Executive Director, Future Milwaukee


Deanna was authentic, engaging and delivered a message that was inspiring and uplifting - much needed given the major endeavors our agency currently faces.

Patty Metropulos, Executive Director & CEO, Kathy's House