Break Free with Ashley Winston

Ashley Winston

If you're ready to embrace authenticity, take action, and live the life God has in store for you, you've found your perfect destination. Join Ashley Winston and her esteemed guests as they share inspiring stories, practical wisdom, and valuable advice on faith, business, and life. With a global reach spanning Africa, Europe, Asia, and the Americas, the podcast has touched listeners' lives in over thirty-four countries. About Ashley: Ashley Winston is a multi-passionate entrepreneur, author, international speaker, business advisor, and founder of the Unstoppable Mentorship Community. With over fifteen years of experience in teaching, advising, and coaching in personal and business settings, she helps people win and provides them with the necessary keys to unlock their peak performance. Her gifts and unique skill set have landed her a wide range of opportunities here and abroad. She has served on the mission field in Port Au Prince, Haiti, and Hyderabad, India. In addition, she has been featured in commercials, films, and on television, including the daytime talk show Rachael Ray, and worked behind the scenes of significant productions. Ashley Winston has worked with over 15,000 women and youth, 50 Chicago Public Schools, and more than 98 organizations, including The Lyric Opera of Chicago and McDonald’s Corporation. In addition, she has written three books, Break Free: Unlock Your God-Given Potential & Unleash Your Unstoppable, You Are Enough, and 7 Secrets to Living Your Best Life, a guide to help you overcome your obstacles and create a life you love.  To learn more about Ashley and her books, please visit her website: TheAshleyWinston.com or follow her on instagram @theashleywinston. Click the link in her bio to stay connected and subscribe to her email list. Receive a wealth of insight, inspiration, and valuable content delivered straight to your inbox.

  1. 12/04/2025

    Heal the Woman, Heal the Home: Why Soul Care Changes Everything

    In this episode of the Break Free Podcast, Ashley has an end-of-year, honest conversation about healing and wellness. She reflects on the women in the Unstoppable Mentorship Community who have embraced the year’s theme: becoming women of wellness in spirit, soul, and body. Special guest Lupe joins the conversation to share her testimony of holistic transformation within the Unstoppable Mentorship Community. When she first entered UMC, she was overwhelmed by family responsibilities, grief, fear, survival patterns, control issues, financial instability, and unhealed childhood wounds. She thought she was ready to launch a business—but God showed her that her soul needed healing first. Lupe reveals how Ashley’s 7 Secrets to Living Your Best Life course challenged her to stop performing, stop task-mastering, and start listening. Through this process, she confronted identity wounds, emotional immaturity, poverty mindsets, and the younger version of herself still making her decisions. She also shares how this inner work transformed her marriage, restored unity in her home, strengthened her leadership, and helped her break generational cycles—so much so that her husband is now taking the course too. This episode is for anyone who feels stuck, is tired of repeating the same cycles, and is ready to become the healed, whole, and aligned version of themselves. Ashley and Lupe offer wisdom, transparency, and hope for women who desire true wellness—not perfection, religion, or performance. Visit the link in Ashley’s Instagram bio @theashleywinston to sign up for her email list and stay connected for weekly insights, mentorship opportunities, and more transformative content.

    Heal the Woman, Heal the Home: Why Soul Care Changes Everything

  2. 11/20/2025

    The Secret Steps God Uses to Multiply What You Build in Private

    In this follow-up episode of The Break Free Podcast, Ashley takes listeners deeper into what happens after you say yes to God. Building on the previous conversation, she shifts the focus from how the journey began to what it looks like when God upgrades your assignment and calls you to return to a familiar place — not to repeat the past, but to operate in a new dimension of maturity, clarity, and spiritual capacity. Ashley reveals how God expands influence by first expanding you — stretching your internal capacity, sharpening your discernment, and preparing you to lead at a higher level. She unpacks the process of recognizing divine timing, embracing refinement, and stepping back into old spaces with new strength, strategy, and authority. Listeners will learn how to discern when God is shifting their assignment, why He sometimes reopens old doors for elevated purposes, and how to navigate the tension between past familiarity and future promotion. This episode offers prophetic insight and practical wisdom for anyone sensing that God is transitioning them from building with basics to building with mastery. If you’ve ever wondered whether God was redirecting you, refining you, or reintroducing you — this episode clarifies the process and empowers you to walk boldly into your next level. Visit the link in Ashley’s Instagram bio @theashleywinston to sign up for her email list and stay connected for weekly insights, mentorship opportunities, and more transformative content.

    The Secret Steps God Uses to Multiply What You Build in Private

  3. 11/06/2025

    Obedience Over Perfection: How Saying ‘Yes’ Ignites Entrepreneurial Success

    In this episode of The Break Free Podcast, Ashley celebrates National Entrepreneurship Month by taking listeners behind the scenes of her own journey of faith-filled entrepreneurship, showing how a simple “yes” to hosting a small women’s group became the foundation for a global movement helping others go from unstuck to unstoppable. She reveals how divine strategy unfolds step by step, emphasizing that true business success is rooted in spiritual alignment, personal growth, discipline, and obedience. Ashley challenges entrepreneurs to stop waiting for perfect plans, full funding, or ideal circumstances, and to trust that God has already written the end from the beginning. She unpacks how growth in business mirrors inner transformation and how alignment with God’s process, patience, and stewardship creates space for sustainable increase and impact. Listeners are reminded that every act of faith, no matter how small, positions them for breakthrough and divine favor. Visit the link in Ashley’s Instagram bio @theashleywinston to sign up for her email list and stay connected for weekly insights, mentorship opportunities, and more transformative content.

    Obedience Over Perfection: How Saying ‘Yes’ Ignites Entrepreneurial Success

  4. 10/23/2025

    PT 2 - Faith, Facts & Freedom: Unlocking the Hidden Connection Between Your Health and Wealth

    In this powerful episode of the Break Free Podcast, Ashley dives deep into the real reason many people repeat painful cycles in life, business, and relationships. Building on part one, she explains that advancement often exposes what’s been hiding in our hearts—and what looks like opposition is often God’s revelation. Ashley guides listeners on the journey from what’s revealed to what’s required for transformation, showing how unhealed soul wounds—especially the need to feel needed—can influence decision-making, attract dysfunction, and distort discernment. Using relatable stories from everyday life, she reveals how emotional patterns like validation-seeking or control can silently sabotage progress. Listeners will learn practical steps to invite God into these areas through repentance, Scripture meditation, and application in real life. Ashley reminds us that true transformation happens when revelation meets consistency—and that breakthrough comes when we begin to live healed, whole, and led by the Spirit of God instead of our wounds. Visit the link in Ashley’s Instagram bio @theashleywinston to sign up for her email list and stay connected for weekly insights, mentorship opportunities, and more transformative content.

    PT 2 - Faith, Facts & Freedom: Unlocking the Hidden Connection Between Your Health and Wealth

  5. 10/09/2025

    PT 1 - Faith, Facts & Freedom: Unlocking the Hidden Connection Between Your Health and Wealth

    In this episode of the Break Free Podcast, Ashley unpacks the spiritual truth that advancement always exposes what’s been hidden. Drawing from personal experiences, ministry insights, and real-life moments from the Unstoppable Mentorship retreat in Miami, she explains how God uses new environments to reveal old patterns, wounds, and cycles that block breakthrough. Ashley teaches that what feels like opposition is often divine revelation—a sign that healing, realignment, or deliverance is needed before elevation. She urges listeners to face their truth instead of hiding behind faith without works, recognizing that ignorance and avoidance keep us trapped in cycles of defeat. Through Scripture and practical wisdom, Ashley calls believers to spiritual warfare awareness—breaking passivity, aligning with God’s voice, and partnering with the Holy Spirit for total wellness of spirit, soul, and body. Because prosperity, health, and purpose are all connected, breakthrough only comes when you confront what’s been conquering you internally so that heaven’s victory can manifest on earth. Visit the link in Ashley’s Instagram bio @theashleywinston to sign up for her email list and stay connected for weekly insights, mentorship opportunities, and more transformative content.

    PT 1 - Faith, Facts & Freedom: Unlocking the Hidden Connection Between Your Health and Wealth

  6. 09/25/2025

    Don’t Miss Your Moment: Why Preparation Unlocks Opportunity

    In this episode of the Break Free Podcast, Ashley shares a powerful lesson on preparation and capacity. Through a story about something as simple as a passport cover and an unexpected boarding pass, Ashley shows how God uses the smallest details to point us toward greater assignments. Preparation is not just practical—it’s spiritual. Drawing from the parable of the ten virgins, she explains how access is available to all, but only those who are prepared with oil—the presence and power of the Holy Spirit—can step fully into destiny. Capacity is what fills the void between revelation and manifestation, and this conversation will equip you to show up ready for the doors God is opening in your life. Visit the link in Ashley’s Instagram bio @theashleywinston to sign up for her email list and stay connected for weekly insights, mentorship opportunities, and more transformative content.

    Don’t Miss Your Moment: Why Preparation Unlocks Opportunity

  7. 09/11/2025

    Step Into Your Harvest: A Guide to Unlock the 4 Stages of God’s Plan

    In this episode of the Break Free Podcast, Ashley unpacks the truth that purpose is not optional. She shares her own journey of discovering purpose and walks listeners through the four stages of purpose—preparation, planting, growth, and harvest. With biblical examples and personal testimony, Ashley explains why adversity is part of preparation, how surrender is required in planting, why growth takes patience and discipline, and what true harvest looks like when our gifts begin to manifest. She also draws a key distinction between purpose (eternal) and assignments (seasonal), reminding us that success, money, or influence without purpose will always leave us empty. This episode is both practical and prophetic—helping you trade frustration for clarity, and emptiness for fulfillment by aligning with God’s plan for your life. Visit the link in Ashley’s Instagram bio @theashleywinston to sign up for her email list and stay connected for weekly insights, mentorship opportunities, and more transformative content.

    Step Into Your Harvest: A Guide to Unlock the 4 Stages of God’s Plan

  8. 08/28/2025

    Loneliness and Connection: Learning When to Let Go

    Friendship is one of life’s greatest gifts—but it can also be one of our biggest struggles when we approach it from a place of emptiness. In this episode of The Break Free Podcast, Ashley offers a raw and honest conversation on what it really takes to build healthy, God-centered friendships. She challenges the tendency to make people our source, reminding us that true fulfillment only comes from God. When we skip that step, we set ourselves up for disappointment—overinvesting, ignoring red flags, or clinging to relationships that have already expired. Instead, Ashley shows us how to first cultivate self-connection and wholeness in Christ so that our friendships are not rooted in lack, but in abundance. With her signature mix of biblical wisdom and practical truth, Ashley breaks down the importance of discernment, capacity, and courage in our relationships. She explains why mismatched capacity leaves us drained, why loneliness is not a curse but a call to preparation, and how to identify the people who are truly equipped to walk with us in our purpose. This is more than a message about friendship—it’s an invitation to realign your circle, release what no longer fits, and step into the kind of authentic, sharpening relationships God designed for you to thrive in. Visit the link in Ashley’s Instagram bio @theashleywinston to sign up for her email list and stay connected for weekly insights, mentorship opportunities, and more transformative content.

    Loneliness and Connection: Learning When to Let Go
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4.9
out of 5
44 Ratings

About

If you're ready to embrace authenticity, take action, and live the life God has in store for you, you've found your perfect destination. Join Ashley Winston and her esteemed guests as they share inspiring stories, practical wisdom, and valuable advice on faith, business, and life. With a global reach spanning Africa, Europe, Asia, and the Americas, the podcast has touched listeners' lives in over thirty-four countries. About Ashley: Ashley Winston is a multi-passionate entrepreneur, author, international speaker, business advisor, and founder of the Unstoppable Mentorship Community. With over fifteen years of experience in teaching, advising, and coaching in personal and business settings, she helps people win and provides them with the necessary keys to unlock their peak performance. Her gifts and unique skill set have landed her a wide range of opportunities here and abroad. She has served on the mission field in Port Au Prince, Haiti, and Hyderabad, India. In addition, she has been featured in commercials, films, and on television, including the daytime talk show Rachael Ray, and worked behind the scenes of significant productions. Ashley Winston has worked with over 15,000 women and youth, 50 Chicago Public Schools, and more than 98 organizations, including The Lyric Opera of Chicago and McDonald’s Corporation. In addition, she has written three books, Break Free: Unlock Your God-Given Potential & Unleash Your Unstoppable, You Are Enough, and 7 Secrets to Living Your Best Life, a guide to help you overcome your obstacles and create a life you love.  To learn more about Ashley and her books, please visit her website: TheAshleyWinston.com or follow her on instagram @theashleywinston. Click the link in her bio to stay connected and subscribe to her email list. Receive a wealth of insight, inspiration, and valuable content delivered straight to your inbox.

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