470: I Didn't See THAT Coming: What Happens When We Hit the Wall, Why God’s Silence Isn’t His Absence, and the 4 CRITICAL Words You Must Embody in 2026
Win Today: Your Roadmap to Wholeness
Release Date: 12/30/2025
Christian Self-Help Is Lying to You. Dr. Henry Cloud on What Real Change Actually Requires.
Win Today: Your Roadmap to Wholeness
SHOW NOTES DESCRIPTION: You have tried harder. You have read the books, made the commitments, restarted the plan, and believed — genuinely believed — that this time would be different. And yet, five years later, you are looking at the same patterns, the same walls, the same version of yourself you were trying to leave behind. The failure is not a motivation problem. It is not a willpower problem. It is something deeper, something that the self-help industry cannot name because naming it would dismantle the entire enterprise. Dr. Henry Cloud joins me for his third conversation on Win Today,...
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Jamie Winship: “You Don't Know What Water You're Swimming In.” The Separation Worldview and the Scarcity Lie Running Your Life.
Win Today: Your Roadmap to Wholeness
You can feel it, even if you have never named it. The tightness around not having enough, not being enough, not doing enough. The reflex to protect what you have before someone takes it. The way your relationships quietly become negotiations, your faith quietly becomes performance, and your inner life quietly becomes a war zone — all while you are calling it prudence, discernment, stewardship, responsibility. You have been living from a worldview. And you probably have no idea which one it is. Jamie Winship returns to Win Today, and this conversation cuts deeper than most Jamie is the...
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Some People Like You Better Broken. Tim Ross on Dysregulation, Curated Narratives, and the Peace That Actually Holds.
Win Today: Your Roadmap to Wholeness
You have been managing something for a long time. Maybe you don't call it that. Maybe it shows up as a low-grade restlessness, a reflexive reaching for the phone, a fullness in your chest that never quite resolves. You've done the spiritual things. You've prayed, you've worshipped, you've pressed through. And underneath all of it there is still something unresolved, something unnamed, something you have quietly agreed to just carry. And the most confronting possibility in the world is that the people closest to you have gotten comfortable with you carrying it, because a version of you that is...
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This Is Why You Keep Having the Same Argument. Jason VanRuler on the Wound Behind Every Fight You Can't Escape.
Win Today: Your Roadmap to Wholeness
You have already tried the conversations. You have tried slowing down, choosing better words, waiting for the right moment. And still something derails it — the same wall, the same disconnect, the same feeling that you are speaking into air. What you have probably not tried is understanding why you communicate the way you do, and more importantly, where that pattern came from. Jason VanRuler is a licensed psychotherapist, author, and nationally recognized speaker whose new book, Discovering Your Communication Type, names a truth that changes everything: your communication style was not...
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Your Jesus Is Too Small. Kyle Idleman on the Domestication of Jesus, Weird Subculture Christianity, and Why a Comfortable Savior Can't Save You.
Win Today: Your Roadmap to Wholeness
You have configured Jesus to fit your life. Not consciously, not maliciously, but you have done it nonetheless. The algorithm of your preferences, your comfort thresholds, your political loyalties, your financial anxieties — they all quietly shape the version of Jesus you bring to church, to prayer, and to your decisions. The result is a Jesus who agrees with you more than he challenges you, who blesses your plans more than he disrupts them, and who functions, if you are honest, more like a life coach than a Lord. Kyle Idleman, Senior Pastor at Southeast Christian Church in Louisville and...
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Everyone Is Spiritual. Very Few Are Discerning. Dr. Joel Muddamalle on The Unseen Battle of Deception.
Win Today: Your Roadmap to Wholeness
You have a vague, unsettled sense that something is off—in the culture, in the church, maybe even in your own spiritual life—but you cannot quite name it, and so you keep moving, hoping it will clarify on its own. It will not clarify on its own. What you are sensing is real, and there is a name for it: you are living in the middle of a war you have not been trained to see. Dr. Joel Muddamalle, theologian and Director of Theology and Research at Proverbs 31 Ministries, joins me for a conversation that is as theologically rigorous as it is pastorally urgent. Joel makes the case that the...
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You're Betraying Your Future Self Every Time You Do THIS. Jon Acuff on Why Procrastination "Protects" You and the Permission to Finally Start.
Win Today: Your Roadmap to Wholeness
You know what you're supposed to do. You've known for a while. And yet here you are, on the other side of another day that didn't deliver what you intended, wondering why you keep choosing the version of yourself that never has to be tested. The uncomfortable truth is that you're not failing because you're lazy. You're failing because procrastination is solving a problem for you—the problem of having to find out who you actually are when the pressure is on. Jon Acuff joins me for a conversation that is equal parts diagnostic and liberating. Jon is one of the sharpest thinkers working...
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You Don’t Want Freedom as Much as You Think You Do. Alex Seeley Confronts Why We Like to Stay Stuck in Error and Delusion.
Win Today: Your Roadmap to Wholeness
Many people say they want freedom. They pray for it, talk about it, and surround themselves with language that sounds like transformation. But beneath the surface, there is often resistance. Patterns persist. Mindsets remain unchallenged. And responsibility is quietly avoided. This week on Win Today, Alex Seeley joins me for a direct and necessary conversation about the work of sanctification and what it actually requires. We examine why so many believers remain stuck in cycles they claim to want to leave, how unchallenged thinking reinforces spiritual stagnation, and why true freedom demands...
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MercyMe’s Bart Millard on Why Suffering Isn’t Your Core Problem and What God Is Actually Doing in Your Pain
Win Today: Your Roadmap to Wholeness
You may be walking through disappointment. You may feel tempted to withdraw. You may not know how to trust God again. This conversation with Bart Millard from MercyMe will help you understand what it means to stay present, stay honest, and allow God to form something deeper in you through what you are facing. You’ll learn: Why suffering can deepen rather than destroy your faith How isolation quietly hinders the healing process Why vocalizing your struggles reduces their power The difference between giving up and true surrender How to trust God beyond specific outcomes Guest Bio Bart...
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Your Soul Is Fragmented. Now What? Heath Hardesty on Why You Can’t Receive God’s Love and the Lie of Self-Improvement Christianity
Win Today: Your Roadmap to Wholeness
Many people today feel scattered. Attention is fractured, emotions are unsteady, and spiritual life feels more like survival than formation. We move from one demand to the next, one distraction to another, and somewhere along the way, the soul begins to splinter. This week on Win Today, Heath Hardesty joins me for a deeply clarifying conversation about what it means to live with an integrated soul in a fragmented world. We examine why so many believers struggle to actually receive the love of God, how discipleship has often been reduced to a subtle form of self-improvement, and why attempts to...
info_outlineWe’re told to trust God when life falls apart and to cling to hope when we feel abandoned. To pray louder when heaven feels silent. But what if the silence isn’t a punishment…but a pathway straight to His presence? What if the wall you’ve hit isn’t the end, but the beginning of a deeper formation? This week on Win Today, I’m re-airing a raw and timely conversation with Dr. Lee Warren—one that took an unexpected turn moments before we hit record. What followed was one of the most personal and Spirit-led conversations I’ve ever had about wilderness seasons, grief, intrusive thoughts, and what to do when you feel like God has gone quiet. I opened up about the last two years of my life. And yet, what I’ve discovered in the silence is this: God’s silence is not His absence. And when everything else shakes, His Word still stands. If you’ve ever felt stuck between the pain of what happened and the fear that nothing will change…if you’ve ever cried out for clarity and heard nothing in return…this episode is for you.
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Episode Links
- Show Notes
- Buy my NEW BOOK "Healing What You Can't Erase" here!
- Invite me to speak at your church or event.
- Connect with me @WINTODAYChris on Instagram, Facebook, Twitter, and YouTube.