Maisha Wynn


Lifestyle Specialist, Maisha S. Wynn, gives credence to the mantra: “a changed mind is a made-up mind.” She is the driving force behind Live To Wynn, a boutique lifestyle firm that provides aspirational and practical guidance for individuals who desire to live their lives more abundantly.

Wynn has made appearances on WGN-TV and WFLD-TV, developed content for various national publications (including Ebony Magazine, Heart & Soul Magazine and Uptown Magazine), led holistic self- empowerment seminars at venues like Bloomingdale’s and the legendary Drake Hotel Chicago, and inspired thousands through her blend of motivational speaking and practical lifestyle enhancement strategies. With a personal journey that includes a massive self-transformation from a size 20 to a size 4, Wynn is able to share her personal philosophy and resilient mindset to inspire and impact change in others.

Prior to forming her lifestyle brand, Wynn was named the National Advertising Director of Uptown Media Group. In her role, she utilized her magnetic personality and unique ability to develop partnerships with luxury brands like Mercedes-Benz, Harry Winston and Salvatore Ferragamo. In this capacity, Wynn created rich opportunities for the Uptown brand to increase its awareness and presence amongst Chicago’s tastemakers and socialites.

Wynn’s stellar academic career was accentuated by participation in student government where she served as the President of her Freshwoman Class and photo journalist for the Spelman Spotlight, and culminated with Wynn earning a bachelor’s degree in English with a minor in Writing from Spelman College. Her goal to share her personal journey with the world has been years in the making. Through her new inspirational book, The Wynning Way: A Guide to Creating Success Your Way,Wynn is able to offer the world a tangible piece of her infectious outlook on life and living.

As an engaged world citizen who embraces the African proverb, “It takes an entire village to raise a child,” Wynn gives back to various charities with her time, resources and talent, such as Dress for Success, The Primo Center and Urban Gateways. She currently resides in Chicago, Illinois.

Learn more about Maisha