Through her tough love, warm nature, and hilarious wit, Ashley Winston brings a powerful and engaging message to a wide range of audiences. From churches to classrooms to corporations, she helps you unlock your God-given potential and unleash your unstoppable in your faith, business, and life.


Hear encouraging stories, inspirational insight and practical advice from the Break Free podcast

Episode 12: What To Do When You’re a Multi-Passionate Entrepreneur

When you're talented, it's no secret that you may find yourself working in many industries and managing multiple skills. It can feel like your life is all over the place or you're going in different directions, and it doesn't help when you hear the critics say, "You can't do more than one thing." We've all [...]

Episode 11: Managing your Time for Optimum Productivity

Feeling busy but unproductive? Or haven't made much of a dent in your 2019 goals? The best leaders and entrepreneurs know how to manage their time for optimum productivity! In this episode, Ashley goes solo and teaches on a recently requested topic: time management. From sight and strategy to systems and structures, she shares 4 [...]

Episode 10: Waging the War on Insecurity

In the Instagram, Snapchat and Facebook world we live in, it’s more tempting now than ever to compare yourself to those around you. Before your day even starts, you can scroll through the top highlights of someone else’s life and decide that as a result of their success and accomplishments, you’re inadequate. The devil is [...]


  • Shamone – Fearless Conference
  • Evan Plummer – Director of Arts Education
  • Jordan LaSalle
  • Lethia Owens, CEO, Game Changers International
  • Kelly
  • Dr. Todd Snead, School Engagement Manager, Lyric Opera of Chicago

Ashley took us on a journey and what a breath of fresh air! Her practical teaching met us where we were, encouraged us to embrace who we are in Christ, and reminded us of the importance of renewing our minds. Thought provoking insight like sitting still to listen to the Holy Spirit will save you money, time, and energy, hit at the heart of “allowing fear to contaminate our faith.” So much rich word - I’m full, ready to work the Word, and let my life speak of the goodness of the Lord!

Shamone Seay, Fearless Conference 2019, Wheaton Christian Center

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

Ashley has consistently pushed the envelope on what it means to be a part of this profession. Her drive to improve the practice of teaching through higher order inquiry, expanded areas of study, and true connection to students make her a constant top pick. We have worked together to design residencies where she implements her core values of experimentation through performance, and school officials repeatedly request her presence. I have personally connected with Ashley due to her warm nature, hilarious wit, and desire to combine artistry with sound business tactics to reflect a sustainable career. She carries these traits into her daily work with students, inspiring them at multiple levels. For these reasons, I consider her a model teaching artist, confident that her path will be one to watch.

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


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