Win Today: Your Roadmap to Wholeness

Somewhere between the prayer requests, the small group answers, and the service rotation, you stopped following Jesus and started working for him. You know what this feels like: the quiet exhaustion under the faithfulness, the sense that God has become an employer and you have become an employee who can never clock enough hours. Tim Timmons joins me from a place most people never reach: 25 years into an incurable cancer diagnosis, months past the death of his best friend, and more alive in Jesus than he has ever been.
Tim is the co-writer of MercyMe's Grammy-nominated "Even If" and the subject of the film I Can Only Imagine 2. We move into the distinction Tim names plainly: working for God is exhausting, and he quit. What replaced it is not resignation; it is something wilder and more demanding, the daily decision to join Jesus in the present moment rather than perform for an audience of One who never asked for the performance. We confront the Christian platitudes that gaslight grieving people, the real distance between surrender and contentment (they are not the same thing, and one of them can be done in fury), and what it looks like to wrestle with God well without letting go.
If you have been managing God's opinion of you rather than following him, this conversation will not comfort you. It will ask you to stop performing and start joining, which is harder and more alive. The question Tim keeps returning to across 25 years of manure and mystery is available to you right now: what if Jesus is here, at work, and not asking for your performance? Stop pretending you have already answered it.
Guest Bio
Tim Timmons is a Nashville-based singer, songwriter, and worship leader who has spent 25 years living with an incurable stage four cancer diagnosis and has emerged not with answers but with something better: a practice. He co-wrote MercyMe's Grammy-nominated "Even If," is the subject of the film I Can Only Imagine 2 (portrayed by Milo Ventimiglia), and recently released Waking Up Again: A Journey of Grief and Gratitude with his wife Hillary. He leads 10,000 Minutes, a nonprofit and podcast built around the question of what happens when Jesus people actually join Jesus in the 10,000 minutes outside of Sunday.
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 already know something is off. The output is there. You're showing up, doing the work, performing at a level other people can see. But underneath all of it, there's a strain you can't quite name — a low-grade exhaustion that has nothing to do with how many hours you slept and everything to do with why you're doing what you're doing. You are working for your identity instead of from it. And no amount of productivity is going to fix a motivation problem. Pentatonix's Kevin Olusola and Donovan Dee Donnell join me today for a riveting conversation.
Kevin Olusola, Grammy-winning beatboxer and member of Pentatonix, and Donovan Dee Donnell, life coach, counselor, and co-author of Designed to Succeed, join me for one of the most theologically loaded conversations this show has ever had. Kevin names something with startling precision: he gave up the ghost — not as resignation, but as full surrender to the Father at the Hollywood Bowl in 2022, performing before thousands without needing their applause because his being was finally more secure than his doing.
Donovan unpacks the mechanics of fear with the clarity of someone who has lived in both the wreckage and the rebuild, walking us through what he and Kevin call the verify-purify-occupy framework, the three-move sequence for dismantling fear's claim before it ever gains a foothold. Together, they trace a thread that runs from identity through core values, through alignment and its guardrails, to the question every person of purpose will eventually have to answer: What are you willing to die for?
This is not a conversation about success. It is a conversation about what happens when your motivation is finally honest enough to be sanctified. It will ask you to do something you have probably been postponing — to go to God with the actual thing, not the acceptable version of it, and let Him work with what is true.
Guest Bios
Kevin Olusola is a three-time Grammy Award-winning musician and beatboxer best known as a member of Pentatonix, the a cappella group that has amassed nearly five billion streams on YouTube. A Yale University graduate who came within a semester of a pre-med track, Kevin traded the expectations of his immigrant Nigerian-Grenadian family for a music career built on the unconventional combination of classical cello and beatboxing — and paid for that leap in ways that eventually led him to something more costly than a career pivot: a genuine reckoning with why he was performing at all. He is also the founder of Imagine Faith Talk, where his platform merges high-performance principles with a Pentecostal-Charismatic faith, and the author of a solo musical project, Dawn of a Misfit.
Donovan Dee Donnell is a life coach, former counselor, and co-author of Designed to Succeed. A self-described introvert with an extrovert's calling, Donovan brings both the rigor of professional coaching and the honesty of someone who has navigated some dark places — including years as a stripper and a long reckoning with what it costs to build a life that isn't afraid of criticism. He is a founding collaborator on the Imagine Faith Talk platform alongside Kevin Olusola, and his coaching work centers on helping people identify the guardrails that protect alignment and do the internal work necessary to keep their motivation honest.
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 found ways to make your wound productive. You turned the thing that broke you into the engine that drives you — and somewhere along the way, you started calling that a superpower. You are high-functioning and deeply exhausted, achieving without arriving, performing your way through life while something underneath quietly starves.
Patrick Lencioni is the founder of The Table Group and the author behind some of the most influential business books of the last twenty years, including The Five Dysfunctions of a Team. But this conversation goes somewhere his work rarely takes him. Patrick opens up about his own diagnosis with OCD — the fear-driven, control-seeking, maniacal cycle of obsession and compulsion — and the childhood wounds that fed it for decades before anyone named what was happening. He and Christopher go deep on the real definition of OCD, its subtypes, including scrupulosity, and the specific way anxiety disorders attach themselves to the things of God and masquerade as faith. They also walk through what the dark night of the soul actually strips from a person — and why that stripping is not punishment but surgery. And Patrick makes the case for something the culture cannot stomach: that refusing to speak truth to someone you love is not kindness. It is cruelty wearing a gentler name.
If you have been performing your faith without living it, checking instead of trusting, arranging your world in exchange for a sense of safety that never quite holds, this conversation is going to name something you have been carrying for a long time. Patrick is not talking from a safe distance. He is still at work. So is Christopher. And what they both know now is that the wound does not become anything worth having until surrender has gone all the way down. That kind of surrender is not passive. It is the hardest thing a person ever does. This conversation will ask you to begin it.
Guest Bio
Patrick Lencioni is the founder and president of The Table Group, a firm dedicated to helping leaders build healthy organizations, and the author of 10 books on leadership and teamwork, with over 3 million copies sold worldwide. His best-known work, The Five Dysfunctions of a Team, has become one of the most widely used business texts in the world, applied by organizations ranging from the Fortune 500 to the military to the local church. He lives and works out of the Franklin, Tennessee area.
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've been filling your days to the brim and calling it faithfulness. Every hour accounted for. Every margin eliminated. You pull it all off, too, and you reach the end of the day unable to say why it felt empty. The people you love most were technically present, but you couldn't really see them. You measured the day by what got done, not by who got loved. And underneath the productivity, if you're honest, there was a quieter engine running — the fear that if you slowed down, you'd have to sit with something you're not ready to face.
Tyler Staton, lead pastor of Bridgetown Church in Portland, author of Praying Like Monks Living Like Fools, The Familiar Stranger, and his newest book After Amen, joins me for what I believe is one of the most theologically precise and personally confronting conversations this show has produced. Tyler has walked through a stage-four cancer diagnosis and come through it with a startling clarity about what the soul actually needs. In this conversation we cover the holiness of unfinished things, how to distinguish Spirit-led submission from fear-driven people-pleasing, what it means to absorb the wrongs of another without becoming a doormat, why approval addiction and genuine love cannot coexist in the same moment, and what Jesus's own relationship to human limits reveals about how we were designed to live.
What Tyler says about the Kingdom of God is worth stopping on. The Kingdom only comes in the present, he argues, and when you're living in your head, toward the next thing, you cannot participate in it. This isn't a productivity hack. It's a diagnosis of a spiritual condition most of us have normalized. The hurry we've made peace with is the very thing severing us from the people we love, the voice of the Spirit we say we want, and the joy we keep expecting to find somewhere ahead. What you'll find in this conversation is not comfort. You'll find a mirror. Tyler names the lie that high-achievers and approval-seekers share in common: that more urgency and more effort will eventually produce the love and belonging we're chasing, and he tells you exactly why that trade will cost you your soul. This conversation will ask something of you. The question is whether you're ready to slow down enough to hear it.
Guest Bio
Tyler Staton is the lead pastor of Bridgetown Church in Portland, Oregon, and the national director of 24-7 Prayer USA. He is the author of Praying Like Monks, Living Like Fools, The Familiar Stranger — a book about encountering the Holy Spirit as a living Person — and his newest release, After Amen: 50 Days of Poetry and Prayer, written in the aftermath of a stage-four cancer diagnosis and the particular clarity that kind of wilderness produces. Tyler lives in Portland with his wife Kirsten, and their three sons. His work sits at the intersection of contemplative prayer, Spirit-led formation, and the kind of pastoral honesty that refuses to separate theological depth from ordinary daily life.
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.

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.