AshleyWinston11-1024x683 - Ashley Winston - Christian Coach and Breakthrough Strategist


My Journey to Breaking Free and Becoming Unstoppable

You know what it feels like to be overlooked. You go to church on Sunday, attend Bible study…and then what? You know there is more to life, more to your faith and more to YOU.

You need a plan. You need direction. You need encouragement and a vision. You need help making your dreams come true.

I know. I’ve been there.

I was raised by a single mom. She was my hero. I grew up seeing her boldly overcome and conquer everything in life with hard work and sacrifice.

Church was a part of my life on and off growing up, but I didn’t have an intimate relationship with God. I carried on in life following my mom’s example and hustled all alone.

But something was missing. I lacked purpose and intentionality. I was just striving and striving but I was never arriving.

One Christmas break during college, I found myself alone, sleeping on the floor of a friend’s Chicago apartment. I came to a turning point. I didn’t want to be alone anymore. Something in me shifted that night and I picked up my Bible for the first time. I read. I cried. I prayed.

My prayer was simple.

“Lord, can you help me?”

And He did.

My life hasn’t been a straight or simple path to success. There have been many obstacles and heartbreaks along the way. But God has guided and directed my every move to where I am now.

I studied theatre in college. My family was concerned about my decision to pursue a career in the arts, because what real jobs are available for theatre majors? I went on to get a Master’s Degree in Arts, Entertainment and Media Management. My plan was to become an executive director for a major youth arts organization.

God had other plans.

After a disappointing internship filled with soul-sucking days of sitting at my desk, I realized my purpose was more than paperwork. My vision began to shift.

God opened the door for me to begin teaching workshops in public schools. Through theatre activities, I was helping students unlock their potential and grow socially, emotionally, and academically.

Over 50+ schools later, my vision and mission started to expand. I was:

Leading professional development training

Presenting to large corporations about personal and professional success

Consulting on a freelance basis for varying creative projects

As God advanced my professional life, He began sending me ministry opportunities. I didn’t know how all the different parts of my life could work together. I struggled to fit Arts + Youth + Business + Ministry all into one cohesive plan. But God knew how to make it work.

At this crossroad, I asked God what I should do next.

“Start a small group.” He answered.

So I did.

One simple step of obedience and less than 12 months later my small group had grown into Break Free Be Unstoppable.

I help women live their best lives and unleash their God-given potential.

My mess became my message.

My pain led me back to God who unlocked my purpose and fulfilled all of His promises in my life.

I know what it’s like to feel stuck and alone. I also know what it’s like to trust God and watch Him completely blow your mind by growing your life in ways you never imagined. I want to help you push beyond your pain so that you can actualize the fullness of your God-given potential.

Live God’s best for your life, starting today!



Bio-300x83 - Ashley Winston - Christian Coach and Breakthrough StrategistAshley Winston is an author, speaker and breakthrough strategist. She empowers people from all walks of life through her books, inspirational messages, training, and online programs. Her approach, processes, and reflective exercises allow participants to identify and break down barriers, both internal and external. She enables participants to take ownership of their lives, by providing the necessary keys to unlock their peak performance. Participants in Ashley’s programs leave the experience with a shifted world view toward results and solutions to problems once considered insurmountable.

Ashley’s skill set and unique ability to engage learners of all levels has enabled her to work with a variety of organizations both here and abroad. Internationally, she has served on the mission field in Port Au Prince, Haiti and Hyderabad, India. Her endeavors in the U.S. include her working with more than 50 Chicago Public Schools averaging over 5,000 youth globally and more than 70 organizations including The Lyric Opera of Chicago, Urban Gateways, Columbia College Chicago, Chicago Arts Partnership in Education, The Progressive Arts Alliance of Cleveland, Game Changers International, Tacom and McDonald’s Corporation. She has touched the lives of youth, teachers, community leaders and entrepreneurs globally. Learners love her.

Through her warm nature, tough-love, high-energy and hilarious wit, she pursues the impossible and accomplishes the unthinkable. Faith in God, and the Word, are her foundation. It is what God has done in and through her that brings freedom and breakthroughs.

Ashley holds a Bachelor of Arts degree in Theater Performance and a Master of Arts Management (MAM) in Arts, Entertainment and Media Management. She received both from Columbia College Chicago. Ashley is the founder and creative director of Break Free Be Unstoppable, a marketplace ministry, that teaches people how to make living free a priority and enables them to unlock their God given potential and unleash their unstoppable.

Connect With

  • It’s Monday. Let’s get it! Whatever you’ve been through this year, know that it’s working for you - all of it! Things might not look the way you thought they would, but it’s working for you. It’s the last official week of the year...let 👏🏾 it 👏🏾 work 👏🏾 FOR you!
  • Love them...but let them go 👏🏾
  • squoze
verb | past superlative of squeeze

When God keeps putting you in tight situations over and over again (making you act right) in order to get the very best out of you, so that you can eat the good of the land. 
Me: God I’ve had enough of this! I’m at capacity. I’m is squoze! God: There's still more. Me: 😑
  • This week, I’ve been wearing one of the many hats that comes with being a multi-passionate entrepreneur (#godsplan 🙃) and this week’s hat is consulting and training leaders that work with youth.👩🏾‍🏫 Today is day 3 of 3 working with a company that connects youth to careers in manufacturing. And all I gotta say is, God will use your gifts any type of way, won’t He?! LVBS. 🤣🤣
The recurrent theme in our leadership discussions: you can’t give what you don’t have. Meaning you can’t give compassion if you don’t have compassion. You can’t help people grow if you are unwilling to do so yourself. YOU can’t give $5 if you don’t have $5, OKAY?! 👏🏾🤣
Leaders get the job done without worrying about the recognition. At the end of the day, we need more of that in organizations. Less ego...more evolving!
  • know at least one person that needs to break free before 2019. 👏🏾 Help get them started. BOGO for Black Friday only. Link in bio!
  • Happy Thanksgiving! Be thankful for what you have; you'll end up having more. If you concentrate on what you don't have, you will never, ever have enough.

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