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 20: Get Over It

Are you handling business or is business handling you? Often times we lack the patience needed to see our dream life and business become a reality. We want everything now and when we don’t see results right away it can be tempting to give up. Don’t give up! God takes each one of us through [...]

Episode 19: Manifesting Your Kingdom Advantage

Are you tired of settling? In this episode Ashley shares a message delivered to Living Word Christian Center about how to partner with God to develop a winning attitude and mindset. Training for reigning is an ongoing process and every point of increase in your life will require you to change. Learn how to overcome [...]

Episode 18: Self Mastery – The Keys to Unlocking Kingdom Wealth & Your Full Potential

What if I told you that your life will never rise above the way that you think? It’s true. God wants His plan and your dreams to come to life, but we have to show up, tell the truth, and do the work in order for those plans to manifest and that work starts with [...]


  • 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


Please fill out the form below to invite Ashley Winston for your next event.

Download this free teaching and learn how to unleash your unstoppable.

    Download this free teaching and learn how to unleash your unstoppable.

      This error message is only visible to WordPress admins

      Error: API requests are being delayed for this account. New posts will not be retrieved.

      There may be an issue with the Instagram access token that you are using. Your server might also be unable to connect to Instagram at this time.

      Loading posts...
      Sort Gallery