

Win Today: Your Roadmap to Wholeness
Art of Leadership Network
Life is complicated, and quick fixes won’t address the deeper challenges you face in your mental, emotional, and spiritual health. "Win Today" provides practical guidance for lasting growth. Each week, you’ll hear from trusted leaders and experts who offer wisdom, insights, and a durable plan to help you overcome obstacles and create real, sustainable change. This isn’t about temporary solutions—it’s about building a foundation for transformation and maturity from the inside out.
Episodes
Mentioned books

Sep 24, 2025 • 1h 10min
457: When God Feels Silent. Evan Craft on The Hardest Questions We Rarely Ask (But Need To), Fighting Cynicism, Charlie Kirk’s Death, The Necessity of Desperation in Faith, Serving the Lord in Anonymity, and What We Receive in the Dark Night of the Soul
Evan Craft, an international recording artist and worship leader, dives deep into the struggles of faith in silence and the value of serving in anonymity. He discusses how wilderness experiences can transform us, revealing the necessity of spiritual desperation. Evan emphasizes questioning with healthy skepticism rather than cynicism, embracing the mystery of suffering, and the power of persistence. He confronts the hardest questions many avoid, all while encouraging a humble approach to spirituality that thrives in the dark nights of the soul.

Sep 17, 2025 • 1h 15min
456: When “Safe Spaces” Sabotage Growth. Katie Davis Majors on False Cliché Christianity, Preventing Bitterness in Your Heart, and When Empathy Hinders Transformation
Katie Davis Majors, founder of Amazima and author, discusses the pitfalls of seeking comfort over growth. She highlights how well-intentioned empathy can stunt spiritual development and how 'safe spaces' may hinder true transformation. Drawing from her experiences in Uganda, Katie emphasizes the need to navigate suffering with authenticity and faith. She advocates for embracing vulnerability within community to foster healing and personal growth, urging listeners to confront their discomfort for a deeper relationship with God.

Sep 10, 2025 • 1h 22min
455: You Don’t Get a Hall Pass from Pain. ESPN’s Lauren Sisler Exposes “Rah-Rah” Christianity, Why Avoidance Costs Us More Than Facing Pain Head-On, and Curating Our Image as Armor
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.

20 snips
Sep 3, 2025 • 1h 4min
454: Comfort Is KILLING You. Tim Timberlake on The Crisis of Convenience, Why God Doesn’t Live Up to Our Expectations, The Problem with Rushing Through Grief, Why God Doesn’t Live Up to Our Expectations, and Manufacturing Breakthrough
Tim Timberlake, a pastor and author of 'The Bumpy Road to Better', tackles modern life's challenges through a faith lens. He argues that chasing convenience often costs us more than it gives, revealing how rushing through grief fractures our future. Timberlake emphasizes the importance of embracing discomfort for genuine transformation and discerning true blessings from mere comfort. He encourages listeners to confront pain, stand firm in their faith, and cultivate deeper connections with God, highlighting that breakthroughs must be authentic to withstand life's tests.

6 snips
Aug 27, 2025 • 47min
453: You’re Not Humble, You’re Hiding. Dr. Les Parrott and Judah Smith Unpack How Humility Becomes Self-Hatred, The Nuclear Power of Spiritual Bypassing, and Why Your Job is Not to Heal Publicly
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.

Aug 20, 2025 • 1h 32min
452: STOP GASLIGHTING YOURSELF. Toni Collier on Emotional Infidelity, Spiritual Manipulation, and the Prison of Isolation
Toni Collier, a dynamic speaker and author, shares her insights on emotional infidelity and the effects of spiritual manipulation. She bravely reveals her journey through trauma, emphasizing that true vulnerability is sacred and essential for healing. Toni challenges the misconceptions surrounding therapy, forgiveness, and the impact of societal pressures on our emotional health. Her conversation encourages embracing community support and authenticity, guiding listeners toward emotional wholeness and genuine connections.

Aug 13, 2025 • 44min
451: What’s Breaking You Isn’t the Pain, It’s the Pattern. Ed Latimore on Emotions, Distorted Thinking, and Toughness That Won’t Heal You
Ed Latimore, a former heavyweight boxer turned Stoic philosopher and physicist, shares profound insights on emotional discipline and self-awareness. He dismantles the architecture of dysfunction, emphasizing how distorted beliefs lead to chaotic lifestyles. Ed explains the importance of confronting deep-seated issues for authentic healing. He discusses how scientific insights on emotions can enhance decision-making and the difference between toughness and true wholeness, advocating for vulnerability as a pathway to personal growth.

Aug 6, 2025 • 1h 1min
450: You’re Talking Too Much. Jefferson Fisher on Ending Arguments, Spotting Manipulation, and Reclaiming Authority in Conversations
Jefferson Fisher, a trial lawyer turned communication expert and author of The Next Conversation, shares invaluable insights on mastering conversations. He delves into the art of slowing down dialogue instead of raising your voice. Fisher reveals the pitfalls of overexplaining and highlights how to spot manipulation in discussions. He emphasizes that restraint fosters trust and clarity, and offers practical tools for leading conversations rather than reacting impulsively. The discussion also covers the impact of social media on communication dynamics.

11 snips
Jul 30, 2025 • 1h 3min
SUMMER BREAK: Jamie Winship on Why Separation Creates Suffering, The Necessary Practice of Self-Emptying, and a Right View of God
Jamie Winship, a thought leader on spiritual formation, dives deep into why separation creates suffering and the transformative practice of self-emptying. He explores how a closed-hand mindset rooted in fear can restrict personal growth, advocating for an open-handed trust in divine providence instead. Winship discusses the necessity of viewing God positively, and how genuine relationships emerge from vulnerability and humility. His insights encourage a shift from isolation to meaningful connections, inspiring listeners to trade anxiety for peace.

17 snips
Jul 23, 2025 • 1h 6min
SUMMER BREAK: Jamie Winship on Getting Unstuck, The Lie of Being Alone, Radical Individualism, and Why Pain is Good
Jamie Winship, an expert on identity and fear, shares profound insights on breaking free from isolation and embracing community. He discusses how radical individualism hampers growth and highlights the crucial role of pain in transformation. Listeners are encouraged to confront discomfort for genuine connection and renewal, challenging the self-centered cultural mindset. Winship empowers individuals to rediscover their true selves, emphasizing the importance of relationships in overcoming feelings of stagnation.