We all want to overcome, but too often, we curate our pain out of view—tidy it up, slap a spiritual platitude on top, and hope time heals what we never confronted. This week on Win Today, ESPN’s Lauren Sisler reveals what happened when her life fell apart at 18. She buried both of her parents just hours apart. And in the wake of that trauma, she didn’t get a “hall pass” from grief. She didn’t get a spiritual fast-forward button. She had to live every moment of it, raw and real. In this powerful conversation, we take on the lies of “rah-rah Christianity,” the armor of image management, and the emotional expense of avoidance. If you’ve ever wondered why God didn’t spare you from the pain… or why it still lingers even though you “moved on,” this episode will meet you where you really live.

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.

There’s a kind of rest that is still ravenous, and comfort alone is costing your soul more than you think. This week on Win Today, Tim Timberlake joins me to name the central lie of our era: that convenience equals progress. God rarely fits into the narrative designed by self‑help culture, and grief is rarely the speed bump we’re told. When breakthrough is packaged and delivered, it disconnects you from the transformative power of pain. Tim unpacks why immediate comfort doesn’t heal—it anesthetizes. Why rushing through grief doesn’t preserve strength—it fractures your future. And why so many believers craft manufactured breakthroughs that collapse when real life tests them. If your fast-track faith feels flat…if comfort makes you morally weaker…or if you've chased progress more than presence, this episode confronts the real cost, and invites deeper formation.

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.

There’s a humility you carry like baggage, and it’s slowly wearing you down. This week, Dr. Les Parrott and Judah Smith join me to dismantle the false humility that masquerades as godliness while laundering shame. Humility becomes self-hatred when vulnerability is avoided and spiritual high-mindedness is mistaken for healing. Layer on top the epidemic of spiritual bypassing—pretending everything is okay—and you get a reluctance to ever speak pain. We unpack why your job is not to heal publicly, how real accountability looks different than performance, and why refusing to stay in the box of pretense is the most subversive spiritual act you can commit. Whether you’ve preached from the platform or hidden behind faith walls, this episode cuts through your shame fortress and lights a path to emotional and spiritual freedom.

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.