At some point, almost everyone hits a wall in their faith. The emotional highs don’t last, the formulas stop working, and the deeper questions won’t stay buried. Midlife, in particular, isn’t just about aging—it’s about confronting what’s real, what’s broken, and what needs to change. And if we’re not careful, we settle for a faith that looks polished on the outside but leaves us spiritually depleted on the inside.

That’s why this conversation with Tim Ross is so crucial. Tim is known for his raw, unfiltered approach to faith and culture—challenging easy answers and pushing beyond surface-level spirituality. In this episode, we’re diving deep into:

• Why spiritual formation in midlife requires a different approach than in your 20s and 30s.
• The right way to heal your nervous system—and why emotional and spiritual health are inseparable.
• Why curiosity and offense cannot coexist—and how learning to sit with discomfort leads to real transformation.
• The deceptive side of being ‘spiritual’—why some of the most "mature" believers are actually the most fragile.

If you feel like your faith has stalled, if you're done chasing the next emotional high, or if you're wondering how to build true resilience in a culture addicted to outrage, this episode is for you.

Listen now and start rethinking what real spiritual growth looks like.

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.

Are you unknowingly addicted to relief? The truth about addiction, emotional numbing, and why real healing requires more than just self-control. This week on Win Today, Ian Cron exposes the truth about addiction, pain, and why we’re all hooked on something. Whether it’s work, achievement, relationships, control, or substances, we all have our own ways of numbing discomfort. But here’s the real question: Is relief keeping you from real change?

• Are we all addicts? The hidden ways we self-medicate pain
• Pain relief vs. transformation: Why numbing doesn’t work
• How the Twelve Steps can lead to lasting freedom—even if you’re not an addict
• Why addiction is a spiritual crisis—and how to find true healing

For over eight decades, the Twelve Steps have led millions out of addiction—not just from substances, but from self-sabotaging behaviors that keep us stuck. As someone who has walked the road of recovery firsthand, Ian knows that the real breakthrough isn’t just in quitting bad habits—it’s in having a spiritual awakening that radically reorients your life.

If you’ve ever felt like you’re stuck in cycles of unhealthy coping, or if you long for real joy beyond self-help quick fixes, this episode is for you.

Listen now and take the first step toward real transformation.

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.

This week on Win Today, we’re peeling back the layers of masculinity, identity, and emotional resilience with Jason Wilson. If you’ve ever felt trapped in cycles of emotional suppression, struggled with the pressure to be strong at all costs, or wrestled with the tension between vulnerability and leadership, this conversation is for you.

Jason is here to expose the myth of the alpha male and reveal why true strength isn’t about dominance, but about wholeness. He’ll challenge us to stop running from the battles that make us feel weak—and instead, step into them with courage.

• Why emotional incarceration keeps so many men stuck
• How culture distorts masculinity—and what real manhood looks like
• Why avoiding pain makes us weak, and how to reclaim true resilience
• The foundation of comprehensive manhood and how it leads to freedom

If you’re tired of surface-level self-help and want real transformation, this episode will challenge you, stretch you, and equip you to pursue maturity in a way that lasts.

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.

This week on Win Today, we’re wrapping up the Formed series with Bethel Music’s Jenn Johnson. Together, we’re exploring the transformative power of worship during life’s chaos. Jenn shares profound insights on breaking free from toxic positivity, anchoring ourselves in God's unchanging nature, and discovering how worship shapes our spiritual resilience and wholeness.

🎧 What You’ll Learn:

• How worship transforms life’s chaos into growth.
• The danger of toxic positivity and the power of wholehearted gratitude.
• Why anchoring in God’s nature leads to lasting wholeness and resilience.

If you feel overwhelmed or struggle to find hope in difficult seasons, this episode will equip you with the tools to experience God’s presence and peace—even when life feels unsteady.

👉 Don’t forget to subscribe, share, and leave a review if this episode encourages you!

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.

This week, we’re diving deep into the theme of spiritual maturity with someone who has profoundly shaped my life: Pastor Loren Covarrubias. Pastor Loren has been a mentor and guide to me since I was a young boy, making this conversation incredibly personal and meaningful.

In this episode, we explore:

• Why people don’t mature and the obstacles that hold them back.
• How to develop spiritual perception to navigate life’s complexities.
• The dangers of mishandling the prophetic and its impact on spiritual growth.
• Why seasons of desolation are often where the Lord does His greatest work in transforming our hearts.

If you’ve ever felt stuck in your faith or wondered how God works during life’s most challenging seasons, this conversation will provide clarity, encouragement, and hope.

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.

This week, we delve into the critical need for a robust theology of suffering in our postmodern culture of self-help and self-directed spirituality. Joining us is Tyler Staton, lead pastor of Bridgetown Church in Portland. Tyler, having personally navigated the profound experience of losing control amidst his battle with cancer, offers invaluable insights. We'll explore how God works through our pain, inviting us into a deeper understanding of His redemptive purpose. Furthermore, Tyler will address the concerning trend of how we've often misconstrued the Holy Spirit, allowing Him to become a tool for self-aggrandizement rather than a source of genuine transformation.

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.

Are you stuck in frustration, wondering why growth feels so hard? This week, Fr. Ronald Rolheiser joins us to uncover the hard truth about maturity: it often leads us into the wilderness. But here’s the good news—those wilderness seasons can purify your faith, dismantle harmful self-sufficiency, and transform your emotional and spiritual health.

In this episode, we’ll discuss:

• Why maturity requires us to let go of control.
• How mystery becomes our greatest ally in navigating life’s challenges.
• The role of disillusionment in spiritual growth.
• What bitterness does to our emotional and spiritual health—and how to break free.
• Fr. Rolheiser’s reflections on life, faith, and wisdom from nearly 80 years of experience.

This conversation will inspire and equip you with the tools to embrace your wilderness season and experience breakthrough in your faith journey.

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.

This week, it's you and me. We’re unpacking how bitterness, cynicism, and unresolved pain can trap us in a cycle of frustration and blindness to God’s work in our lives. Drawing from Luke 4 and Mark 6, we’ll explore how the condition of your heart affects your ability to heal and mature. If you’re feeling stuck, weighed down by offense, or questioning why breakthrough feels out of reach, this conversation will give you practical tools and biblical wisdom to take the next step toward transformation. And I want to start our series here, because, in the weeks that follow, I want you to receive from our guests with an open mind and heart, unencumbered by issues like bitterness, cynicism, and unresolved disappointment.

🎙️ Joining us this month in our series: Father Ronald Rolheiser, Tyler Staton, Loren Covarrubias, and Jenn Johnson from Bethel Music.

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.

Hey friends, happy new year! I'm excited to share that coming to the podcast this week and running for the next several weeks is Formed, our annual series on spiritual formation. This week, I'm kicking off the series with a teaching on "How a Hardened Heart Blocks Healing and Maturity." Next week, Father Ronald Rolheiser joins us to discuss "Why Maturity Leads Us Into the Wilderness and Dismantles Self-Sufficiency." In two weeks, Tyler Staton teaches us how to lose the illusion of control. On January 22, one of my heroes, Pastor Loren Covarrubias joins us to talk about how to develop spiritual perception and why few believers pursue maturity. And on January 29, Jenn Johnson from Bethel Music joins us to talk about the value of worship in our formation journeys. No doubt, this will be a powerful series. See you on Wednesday, January 1, 2025.

This week, we delve into the hidden forces shaping our world. Veteran journalist Rod Dreher, author of "Live Not by Lies," joins us to discuss the dangers of soft totalitarianism disguised as niceness and comfort. We'll explore censorship, the silencing of dissent, emotional fragility, and the impact of secularism and therapy on our spiritual lives. This conversation is a deep dive into the complex issues affecting our mental, emotional, and spiritual health.

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.