Ashley Winston is a speaker, multi-passionate entrepreneur, author, and business advisor. With over fifteen years of experience teaching and advising in personal and professional settings, she helps people win and provides them with the necessary keys to unlock their peak performance.

From classrooms to churches to corporations, Ashley has worked with over 15,000 women and youth, 50 Chicago Public Schools, and over 70 organizations, including Tacom, The Lyric Opera of Chicago, and McDonald’s Corporation. Ashley has also served on the mission field in Port-Au Prince, Haiti, and Hyderabad, India. She has been featured in commercials, films, and television, including the talk show Rachael Ray, and worked behind the scenes of major productions. Ashley speaks to a wide range of topics. Her dynamic background, authenticity, and business expertise allow her to equip, empower, and extraordinarily relate to leaders from all walks of life.

In addition, Ashley is a firecracker and very entertaining, delivering the necessary truth and tough love, helping the world navigate the wild adventures of faith, business, and life. Ashley is the creator and host of The Break Free Podcast, which has a global reach with listeners in Africa, Europe, Asia, and North and South America. She is the author of three books, Break Free: Unlock Your God-Given Potential & Unleash Your Unstoppable, You Are Enough, and 7 Secrets to Living Your Best Life, a guide to help you overcome your obstacles and create a life you love.


  • Evan Plummer – Director of Arts Education
  • Adriana Testimony – Women’s Pastor & Entrepreneur
  • Lethia Owens, CEO, Game Changers International
  • Kelly
  • Dr. Todd Snead, School Engagement Manager, Lyric Opera of Chicago
  • Rebecca

Ashley Winston has provided professional development experiences for teachers and emerging leaders in Chicago Public Schools. Her approach, processes, and reflective exercises allowed participants to identify and break down barriers, both internal and external, to envision action steps to build community, and to develop strategic partnerships to assist in reaching one's goals. Participants in Ms. Winston's programs leave the experience with a shifted world view toward results and solutions to problems once considered insurmountable.

Evan Plummer, Director of Arts Education, Department of Arts Education/Chicago Public Schools

I always thought that these giants needed to be defeated by me, alone. And I had all these strategies and all these things that I wanted to do, and all I got was tired and frustrated with not seeing the results that I wanted to see, with not feeling secure with my identity in Christ, with knowing all the theory and just not being able to tap into it in my real life. I guess I never expected this to impact my life in so many levels, because I only thought it’s going to like free me in an emotional level or spiritual level. But the changes that the Lord has done in my life through my coaching with Ashley, has impacted not only my emotions and my thought life and my spiritual life, it has impacted the way I do business; it has impacted the way I do ministry; it has impacted my leadership; it has impacted my personal relationships.

Adriana Murillo, Women's Pastor & Entrepreneur

One of the most fun and powerful presentations our group has ever experienced. I can’t wait to implement what we learned.

Lethia Owens, CEO, Next Level Branding & Marketing

Wow. You just got to see Ashley work. I mean, I've really never seen anybody work a room the way that she does. Her energy is electric, it's contagious. She connects with people immediately and she kind of has to because she is getting in your business on today. She's cutting through all of the fluff. She's cutting through all of the excuses so that you can be the very best version of yourself because that's her business. That's what she's here to do.

Kelly McMath, Culture Coach & Leadership Development Specialist

Ashley Winston does an incredible job engaging participants in her workshops and making the content relevant to classroom practice. She worked collaboratively with us to develop a customized agenda and resources that specifically targeted the needs of our organization and our partner teachers. Ashley masterfully balances her artistic and creative expertise with the educational rigor required for the 21st-century classroom. She understands the challenges teachers and artists face and was able to provide effective strategies that elicit the best from teachers and students.

Dr. Todd Snead, School Engagement Manager, Lyric Opera of Chicago

In a word, working with Ashley was transformative. Whether we are talking about growing in God, in business, or as a person, her questions and counsel help me get clear on what is holding me back, get past it, and move forward at warp speed. My money doubled month over month, I have more clients now than I’ve ever had before, and my programs, offerings, and services are expanding. I couldn’t have done it without her. She is anointed, she is loving, she is a force of nature! She loves God and she loves His people, and she is good at what she does. She gets results, she lives results, and she will help you get the results that you want in your life.

Rebecca Watson, Leadership Coach



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