Ask Ashley Q&A: Break Free Book

August 1, 2019

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Ask Ashley Q&A: Break Free Book


It’s been one year since the release of the Break Free Book and what better way to celebrate than with a Q&A blog post! I always get so many questions about my entrepreneurial journeys and my process of writing the Break Free Book. Check out my answers to your frequently asked questions. I pray that it blesses you!


What’s the story behind writing the break free book?

Well, the story is that God told me to write the book, so I did. That’s the shortest version lol.

But essentially, God put it on my heart to write a book back in 2011. At that time, I was a brand new Christian. I was just getting to know what it really meant to walk with God and I had an idea to write a book called the Go Button. It was all about how to help people get going on those things that God put in their heart to pursue, whether that was writing a book or building a company.

But I really didn’t know much because I was a brand new Christian. I got stuck trying to figure out what to say and eventually, I stopped writing. However, as God began to grow me spiritually and take me on my own journey of being an entrepreneur, He put it back on my heart to start writing again.

Around the same time, I met a woman in Atlanta while I was there for business and we exchanged contact information. She reached out to me at the top of 2017 and

She said: Hey, Ashley! God put you on my heart. How are you doing?

I said: Hey, I’m doing great.

She said: Well what did the Holy Spirit tell you to do this year?

I’m thinking, “Lady, you don’t know me. What do you mean what did the Holy Spirit tell me to do?”

God will use people in the most amazing ways won’t He? But I told her, “The Lord’s been speaking to me about moving into entrepreneurship and beginning to build my own company. I don’t know if it’s ministry or business related. I’m still trying to figure it out, but He also told me to write a book.”

She said to me, “Yes, that’s what God put on my heart to tell you. He wants you to finish writing the book. You need to finish it this year.”

I was like, “All right. Well if that’s not clear, I don’t know what  is.”

So I got serious about writing! But I still didn’t have the confidence to do it solo. I was really concerned about my readers being able to understand and apply what God gave me to share. So I prayed and asked Him to send some help! Praise the Lord! He did!

I ended up connecting with a young lady through a freelance website that lived all the way in Costa Rica. The details of this divine connection are too long to share in this short blog post, but just know that it was God and we went to work!

The idea behind the book was to help people overcome internal and external barriers in their lives that prevents them from maximizing their potential and from pursuing the plans and purposes of God. It was the Go Button remixed lol.

A lot of times, we know what God wants us to do, but we’re either afraid or we lack the discipline needed to actually go out and pursue those ideas, dreams, or projects. But if we want to prosper, we need to obey God.

If you are willing and obedient, you will eat the good things of the land; – Isaiah 1:19

What is your definition of an entrepreneur and how did you become one?

I believe an entrepreneur is someone who is willing to take a risk or someone who discovers a need and decides to fill it. I always say entrepreneurs eat what they kill. I know that sounds bad, but it’s true. Entrepreneurs go to work, they build things that are in their minds, and they create opportunities for others. They solve problems.

I became an entrepreneur because God was telling me to do it lol. In the beginning of my career, I had no interest in being one. I REALLY wanted to work a 9-5 that had a great salary and amazing benefits. Let’s just say, God had other plans.

At the time, I was an independent contractor working as a teaching artist in a variety of schools. I facilitated workshops rooted in the principles of personal and professional development for students and teachers. Essentially, I would find creative ways to engage learners of aIl levels in order to help them maximize their potential.

When I reached the ceiling in that industry, I started thinking about what was next. I knew that it was time to make a shift, but I didn’t know how. I struggled looking for mentors and other opportunities that matched my skill set, but nothing landed. And after a couple of disappointing contractual situations, I started to really seek God. (I talk about this in the 7 Secrets book. Grab the first chapter for free here!)

I prayed and I was like, “God, what do you want me to do next? I feel like I’m tapped out on this level. What’s my next best move?”

God told me to start a small group at a coffee shop across the street from my house and I did! I met with women monthly and I started to develop content, curriculums, and programs that would help them on their entrepreneurial journey or in their personal development.

Every time I met with them, I would just listen for their needs. Whatever they told me they needed, I would go create it. And eventually (about 6-12 months later), that small group turned into what is now considered Break Free Be Unstoppable.

So essentially, I transferred the skill set that I used working in the schools to working with people online through courses, live teachings, and private coaching. And from there, God began transitioning me into speaking engagements.

So no matter where you feel like you are on your entrepreneurial journey, know that God is faithful! Seek Him with your full heart and you will find the path that He has predestined for you to take. He will give you instructions and tell you what to do next, but the victory is won through your obedience.

So I’m wondering… What was the last thing God told you to do? Whatever it is, do that.

How did you get your first coaching client?

I get this question a lot!

I got my first coaching clients by writing down a list of everyone I knew that I thought would be interested in joining my small group and signing up for my course. I had about 30 people on the list and I just went through and called every single person.

Honestly, I was really discouraged because I thought that a lot of the people I called would support me. I thought that they would at least be curious enough to come check out what I was doing, but they didn’t.

Ever been there? Like God tells you to do something and you don’t see the results right away?

But I kept calling. I sat in my house and called those 30 people. I was afraid. I was scared. I didn’t know everything I was going to say even though I had read the books and listened to all the sales gurus, but I just kept putting myself out there. I stepped out on faith and trusted God.

Someone finally said yes (Glory to God!), and then she went and told somebody who told somebody else, and we’ve been coaching people ever since.

What is the hardest part about being an entrepreneur?

I talk about this a lot in chapter 8 of the Break Free Book! It’s titled, How Bad Do You Want It? The most challenging part about being an entrepreneur is managing your mind. A lot of people want to be entrepreneurs, but they don’t have the mindset to match their desire. You really, really, really have to have a strong mind if you are going to persevere through all the ups and downs that come with being an entrepreneur.

That’s why reading the Bible is so important! The Word of God renews our mind daily. It aligns us with God’s way of doing things (operating in faith).

At the end of the day, you have to be absolutely convinced that God is for you. You have to trust that whatever He called you to, He will bring you through. Chapter 5 of the Break Free Book, Transform Your Thinking, talks more about this and teaches you how to align your thoughts with God’s Word and His promises for you. It details the importance of being the gatekeeper of your thought life and how that connects to a more fulfilling life.

Are you planning to write any more books?

I have written two other books since Break Free!

One is a mini 15-day devotional called, You Are Enough, and it’s about understanding your identity in Christ.

We face thousands of opinions about who we should be, what we should look like, or what we should have accomplished by now. We battle with comparison, we question our significance and we wonder if we’ll ever break free from what other people think.

I wrote this book because it’s time to stop listening to these voices. It’s time to let go of our past and embrace our future. It’s time to increase our faith and walk in the fullness of God’s promises.

This devotional will help you get going in the morning and it will help you start your day with the right perspective. Learn how to overcome your insecurities and walk fearlessly in who God has made you to be. The time to be secure in who you are is now!

And then my most recent book is called 7 Secrets to Living Your Best Life. It’s my favorite book that I’ve written so far! I love it because it cuts out all the fluff and it tells you exactly how to manage the in-betweens of life.

There may be breakups, life transitions, unexpected events, and moments that leave you feeling like moving forward is impossible, but it’s possible! You weren’t meant to stay stuck. God has big plans for you and He doesn’t want you wasting time and energy going around the same mountains that keep you frustrated or fearful.

God revealed these 7 secrets to me and they will encourage you to break free from whatever’s been holding you back so that you can live a life you love. Grab the first chapter for free here!

Will I write any more books? Yes, there are some more books coming, but you’ll have to stay tuned!

Well I hope you enjoyed getting to know a little bit more about me and about the Break Free Book! What other questions do you have? Tell me in the comments below and you might find your answer in another Q&A post!

Post by Ashley Winston

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