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

  • In the social media world, we face thousands of opinions about who we should be, what we should look like, or what we should have accomplished by now. There’s a huge temptation to compare ourselves with others, question our significance and so many wonder if they’ll ever break free from what other people think.

Nobody really wants to talk about this (because many leaders are struggling with this too), but it’s trueeeeee…😓 It’s time to stop listening to these voices! A few years ago, God led me to write a women's devotional all about this type of stuff. Let’s just say it was not my best work. Have you ever looked at your old journals and been like 🙃😬? Anyway, I reworked it and with a little bit of elbow grease and vulnerability, it’s finally finished just in time for women’s month. Sorry fellas, you know who runs the world. Just kidding. 🤗

The You Are Enough mini devotional takes you through 15 days of encouragement that will help you embrace your identity in Christ with confidence. 💪🏽 Stay tuned! Coming March 2019! 📅
  • Come BE F E A R L E S S with me March 15th & 16th at Wheaton Christian Center. I am super excited about speaking at this amazing conference hosted by the wonderful @graciouswomenministry. Plus, I'll be doing a BOSS UP VIP life and business coaching intensive for a small group of women during lunch (spots are limited and you gotta sign up through the conference app for that). Listen...if you are trying to get your life in 2019 you need to be there. 👏🏾 It's time to take our faith to another level!The link to register is in my bio. 🔗 #HappyMonday
  • Happy Valentines Day! 💕

It’s February 14th so you know what today means! And if you thought the Break Free podcast, you’re absolutely right!  The Real Relationship Talk Part 2 is now live. If you have an ear to hear, 👀 check out the episode at the link in my bio.
  • Rise and Shine! ☀️I hope your week is off to a great start. Meanwhile back at the ranch, I’m still being tortured by @iamfly_ 😖 It's my first week back since early December...y’all pray my strength. 
The struggle is real 👏🏾 Becoming stronger requires us to be uncomfortable for a period of time! In order to build new strengths, we have to break old mindsets and habits. 
When we embrace the conditioning in our spiritual gym necessary for the journey, we unlock our full potential. There is always a process before progress. Stick with it! #HappyTuesday #HealthIsWealth
  • *clears throat* (drum roll please)


I know I fell off (majorly 😬), BUT join me on the 1st of every month for real talk about REAL life! If you’re new to Break Free Be Unstoppable, the Break Free podcast is all about showing up, telling the truth and doing the work so that we can live God’s best for our lives.

In the show, you’ll hear stories and get practical advice on how to apply biblical principles so that you can see yourself the way that God sees you, elevate your faith, and align your actions with what you say you want so that you can unleash your unstoppable.💥 February’s episode will actually be released on Valentine’s Day for The Real Relationship Talk Pt. 2 with my friend and licensed clinical therapist, @tiffanyeverage. Get ready for the laughs! I can’t wait for you to tune in. 🎧
  • I’m going back to Cali 🎶😎🌴 Cause ya girl is tired of this -35-degree weather in Chicago! Last month, I took a trip to LA and I had the 👏🏾best 👏🏾time! I wasn’t sure if I was going to take the trip cause Cali ain't cheap especially after Christmas 😅, but I felt led to step out in faith and God surprised me in so many more ways than I can explain in this post cause y'all only got a 2-second attention span on IG. 🤣

But let me just encourage you.

Don’t look at what you have naturally. Sometimes, you have to step out in faith and trust God even when things don’t make sense. Of course, you have to use wisdom, but when you feel God leading you to do something, timing is everything. Make the move.

Like I always say, He knows the plan! Be open to whatever He wants to do in your life this year and watch Him respond to your faith in His ability and not your own willingness to make something happen. He might even take you to Cali 🏄🏾‍♀️ or Cambodia! 👀

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