Win Today: Your Roadmap to Wholeness

There is something underneath the anger you can't quite name. It sounds like disappointment. It feels like betrayal. And it has God's name on it. You prayed. You believed. You held on as long as you could. And then the thing you were afraid of happened anyway. So somewhere in the quiet, you decided — without maybe ever saying it out loud — that He let you down. That He was responsible. That if He were really good, really powerful, really in charge, this would have gone differently.
Ryan Maher joins me for a conversation that goes straight to the root of that wound. Ryan is the founder of The Prayer Channel and Trust God Bro, the most-followed Christian channels on Instagram, and the author of The God Worth Trusting — a book born out of losing his mother to addiction, losing his friend Brett, and losing his faith in the version of God he'd been handed. What he discovered in that wreckage was not a tidy theology but something far more durable: a distinction between a God who controls and a God who is sovereign, and why confusing those two things has done more damage to the church's trust than almost anything else. We cover the difference between sovereignty and control, what it actually means that God is good at the level of nature and not just activity, and why the phrase "everything happens for a reason" is not only unhelpful; it's a theological lie.
If you have walked through something that feels impossible to reconcile with a good God, this conversation will not give you easy answers. What it will give you is a more honest starting place — and the invitation to build a history with the Lord that holds when the circumstances don't. The question is not whether you can trust Him. The question is whether you are willing to let scripture define who He is rather than letting your worst moment do it.
Guest Bio
Ryan Maher is a pastor and evangelist who uses every digital tool available to share the Gospel, reaching hundreds of millions of people each month through the ministries he has founded and leads, including The Prayer Channel — the number one most popular broadcast channel on Instagram. He is the author of The God Worth Trusting: Restoring Faith in a Good God, a book he describes as the resource he wished someone had handed him in his own darkest seasons. Ryan and his wife, Brittany, are based in Michigan.
Show Partner
SafeSleeve designs a phone case that blocks up to 99% of harmful EMF radiation—so I'm not carrying that kind of exposure next to my body all day. It's sleek, durable, and most importantly, lab-tested by third parties. The results aren't hidden—they're published right on their site. And that matters because many so-called EMF blockers on the market either don't work or can't prove they do. We protect our hearts and minds—why wouldn't we protect our bodies too? Head to safesleevecases.com and use the code WINTODAY10 for 10% off your order.
Episode Links
Show Notes
Buy my 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.

You have more knowledge than you've ever had, and somehow you're more tired. More guarded. More prone to walk into a room and see everything wrong with it before you see anything right. You used to believe things would get better. Now you believe you've simply seen enough to know they probably won't. You call it wisdom. But it might be something else entirely.
 
Carey Nieuwhof joins me for a conversation I've been looking forward to for years, and he opens up in a way I did not expect. At 61, in the wake of 29 simultaneous external stressors, a rare blood disorder that nearly took his life, aging parents, the death of a father-in-law, and the loss of the physical sanctuary that had been his refuge, Carey is navigating what grief actually looks like for a leader who spent two decades not grieving anything. The phrase that has stayed with me since this conversation is one his mentor gave him 25 years ago: ministry is a series of ungrieved losses. We cover what that means in practice, why cynicism is not a character flaw but a predictable outcome of accumulated knowledge without adequate grief, how the shift from fluid to crystallized intelligence changes what leadership should ask of you in your 40s and beyond, and what Carey and his wife Toni are actually doing, not just saying, to finish well.
There is something here that will not comfort you the way you're hoping to be comforted. Carey is too honest for that, and this episode is too important for that. If you have been running at a pace that leaves no room to feel your losses, this conversation is going to cost you something. Sit with it. Let it do its work.
Guest Bio
Carey Nieuwhof is a former attorney and pastor who leads one of the most listened-to leadership podcasts in the Christian space, with more than 800 episodes and over 36 million downloads. He is the author of several books, including the bestselling At Your Best, and the founder of the Art of Leadership Academy, a growing community of more than 20,000 leaders. He spent over a decade as a lead pastor north of Toronto before stepping away to focus on helping leaders at scale. He has studied burnout, cynicism, moral failure, and the patterns that separate leaders who finish well from those who don't. He brings to this conversation more than two decades of pattern recognition built at the intersection of personal suffering and serious study.
Show Partner
SafeSleeve designs a phone case that blocks up to 99% of harmful EMF radiation—so I'm not carrying that kind of exposure next to my body all day. It's sleek, durable, and most importantly, lab-tested by third parties. The results aren't hidden—they're published right on their site. And that matters because many so-called EMF blockers on the market either don't work or can't prove they do. We protect our hearts and minds—why wouldn't we protect our bodies too? Head to safesleevecases.com and use the code WINTODAY10 for 10% off your order.
Episode Links
Show Notes
Buy my 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.

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, and what he brings to the table this time is a confrontation with one of the most quietly destructive lies inside Christian growth culture: that knowledge is enough, that effort is enough, that the right tips applied with sufficient sincerity will eventually produce the life you want. Cloud dismantles that lie at the root. He explains why strength always begins in weakness, why your limitations are not obstacles to your growth but the very doorway through it, and why the passage everyone quotes — "the truth shall set you free" — has been systematically separated from the condition that precedes it. We also go deep into the relational patterns that quietly destroy families, churches, and teams: the victim-rescuer-persecutor triangle and how triangulation turns ordinary conflict into a cycle of division no one can escape from the inside. And Cloud offers one of the sharpest cultural diagnoses I have heard in years — on what the word "triggered" has come to mean and why its inflation is itself a sign of something unhealed.
If you have been doing the work but not getting anywhere, this conversation will name what is actually going on underneath the surface. But it will not let you stay comfortable in the naming. Something is required of you: not more effort, but a different kind of openness — the kind that begins with admitting you cannot do this alone.
Guest Bio
Dr. Henry Cloud is a clinical psychologist, leadership consultant, and New York Times and Wall Street Journal bestselling author whose books have sold nearly 20 million copies worldwide. His work integrates psychological science and biblical wisdom to address the deepest patterns that keep people and organizations from genuine growth. He consults with CEOs, Fortune 500 companies, and high-net-worth family offices, and he is the founder of drcloud.com, which hosts his personal growth platform.
Show Partner
SafeSleeve designs a phone case that blocks up to 99% of harmful EMF radiation—so I'm not carrying that kind of exposure next to my body all day. It's sleek, durable, and most importantly, lab-tested by third parties. The results aren't hidden—they're published right on their site. And that matters because many so-called EMF blockers on the market either don't work or can't prove they do. We protect our hearts and minds—why wouldn't we protect our bodies too? Head to safesleevecases.com and use the code WINTODAY10 for 10% off your order.
Episode Links
Show Notes
Buy my 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.

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 founder of Identity Exchange and author of the new book The War of Worldviews, and for decades, he has brought peaceful, identity-rooted solutions into some of the most dangerous conflict zones on earth. What he has learned in war-torn regions, maximum-security prisons, and international diplomacy is this: every conflict, without exception, is a worldview problem before it is a behavior problem. There are only two worldviews. The separation worldview, which is built on scarcity, runs on fear, and always ends in self-protection and self-promotion. And the connection worldview, which is grounded in abundance, operates from love and produces self-emptying, other-focused transformation. We also dig into why identity alone isn't enough if the worldview carrying it is toxic, the staggering difference between influence and production, what Moses was actually warning Israel about through the story of Joseph, and why Daniel's refusal to bow to the empire changed three dynasties while Joseph's compliance led to his own people's bondage.
If you have been calling your fear something else — and there is a good chance you have — this conversation is going to name it. You will have to decide what to do with what you hear. That decision will shape everything else.
Guest Bio
Jamie Winship is the co-founder of Identity Exchange and Identity Impact, training and consulting agencies that have helped leaders across professional sports, government, law enforcement, business, and international diplomacy discover their true identity and operate from it under pressure. After a distinguished career in law enforcement in the Washington DC metro area, Jamie earned a master's in English and spent years working in some of the world's most dangerous conflict zones — Indonesia, Jordan, Iraq, Palestine, and Israel — developing his Identity Method, a process of identity transformation that resolves inner conflict and opens new levels of creativity and resilience. He is the author of Living Fearless and the new book The War of Worldviews.
Show Partner
SafeSleeve designs a phone case that blocks up to 99% of harmful EMF radiation—so I'm not carrying that kind of exposure next to my body all day. It's sleek, durable, and most importantly, lab-tested by third parties. The results aren't hidden—they're published right on their site. And that matters because many so-called EMF blockers on the market either don't work or can't prove they do. We protect our hearts and minds—why wouldn't we protect our bodies too? Head to safesleevecases.com and use the code WINTODAY10 for 10% off your order.
Episode Links
Show Notes
Buy my 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.

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 fractured and functional and never-quite-well is a version of you they know how to manage. Tim Ross joins me for a conversation that is equal parts pastoral and surgical.
Tim is the host of The Basement podcast and the author of The Missing Peace: How to Be Held Together When You're Falling Apart, and what he brings to this conversation is not theory. In 2019, Tim's life was simultaneously at its most visible and its most misaligned, and what cracked the surface was not a catastrophic failure but something quieter and stranger than that, a spray-paint can and six cans from Home Depot on a Saturday night, and elders kind enough to hold a mirror up. We trace that inflection point all the way to a theology of nervous system regulation grounded not in Polyvagal theory alone but in Mark 4, in John 14, in the peace that Jesus left as a Person and not a feeling. We talk about dysregulation as detachment from peace, about why a regulated person can discern between the agitator and the agitated when a dysregulated one can only rebuke everything, about the narratives we have fallen in love with because the work of changing them is simply too much to want to face. We talk about what it costs to get free, and why some of the people in your life are quietly counting on you not to.
The free you will not tolerate what the bound you did. Tim said that near the end of our conversation, and it's the kind of sentence that doesn't settle quietly. This episode will not let you stay comfortable with a curated peace. It will ask whether what you're calling maturity is actually avoidance, whether what you're calling faith is cowardice dressed up, and whether you're ready to throw off the outer garment and run.
Guest Bio
Tim Ross is the host of The Basement podcast, one of the most widely followed voices at the intersection of faith, mental health, and honest human experience. Tim has spent more than 27 years in the work of formation, and his shift from the pews to podcasting has extended his reach to millions. His newest book, The Missing Peace: How to Be Held Together When You're Falling Apart (Thomas Nelson, 2025), is a theology of peace rooted in the person of the Holy Spirit and grounded in the lived reality of nervous system regulation. He lives in Dallas with his wife, Juliette, and their sons Nathan and Noah.
Show Partner
SafeSleeve designs a phone case that blocks up to 99% of harmful EMF radiation—so I'm not carrying that kind of exposure next to my body all day. It's sleek, durable, and most importantly, lab-tested by third parties. The results aren't hidden—they're published right on their site. And that matters because many so-called EMF blockers on the market either don't work or can't prove they do. We protect our hearts and minds—why wouldn't we protect our bodies too? Head to safesleevecases.com and use the code WINTODAY10 for 10% off your order.
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Episode Links
Show Notes
Buy my 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.