Why We'd Rather Trick Ourselves Than Train Ourselves. Geoffrey Cain on What Steve Jobs's Wilderness Years Can Teach You About Failure, Ego, and Comeback.
Win Today: Your Roadmap to WholenessShow Notes
You know the feeling. The world that once held shape around you — the role, the identity, the thing you built or pursued or believed about yourself — has come apart. And instead of leaning into the chaos and learning what it has to teach you, you've found a more comfortable option. You've constructed a story. A controlled version of events where you're still the hero, where the failure makes sense, where the disruption is somebody else's fault. The snow globe stays intact on the countertop. You shake it and admire the beauty. And you tell yourself the simulation is real. Geoffrey Cain joins me for one of the most unusual and honestly riveting conversations this show has ever produced. Geoffrey is a national columnist and the author of Steve Jobs in Exile, the definitive account of the twelve wilderness years between Jobs's ousting from Apple in 1985 and his legendary return in 1997. What emerged from that research is something that has far less to do with Silicon Valley than it does with the interior architecture of every human being who has ever hit rock bottom and had to decide what to do next. We cover four lessons the wilderness teaches every person who enters it — how it harnesses potential, tests motivation, forces maturity, and compels you to finally confront yourself. We dig into ego death: what it actually is, why the ego is not the enemy it's made out to be, and why the unchecked ego eventually destroys every relationship it touches. We examine the moment Jobs stood at the edge of personal bankruptcy, nearly broken by his own brilliant volatility, and chose — slowly, painfully, imperfectly — to start releasing control and trusting the people around him. And we talk about the universal human tendency to choose fantasy over reality, comfort over confrontation, and the seductive lie that we can trick ourselves into maturity without ever doing the actual work of being transformed. Here is what this conversation will ask of you: it will ask you to look honestly at the place where you are substituting the snow globe for the actual world. It will ask you to name the interior flaw you have been circling and avoiding rather than confronting. It will ask you to consider that the wilderness you are in right now is not a detour from your story but the very place where your story is being written. You can leave this conversation inspired, or you can leave it changed. Those are two very different exits. Guest Bio Geoffrey Cain is an award-winning author and national journalist whose work has appeared in The Wall Street Journal, Time, The Economist, Wired, and The Spectator. His previous books — Samsung Rising and The Perfect Police State — established him as one of the most rigorous and compelling chroniclers of technology, power, and human behavior writing today. His newest book, Steve Jobs in Exile, draws on previously unpublished documents, unbroadcast footage, and new interviews with Jobs's closest colleagues to tell the definitive story of the twelve years that transformed a volatile, brilliant young founder into one of the most consequential leaders in modern history. Geoffrey writes the Substack newsletter The Burner Files and is a managing partner at Alembic Partners. 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.
More from Win Today: Your Roadmap to Wholeness
Somewhere along the way, the performance became the person, and now you can't tell where the effort to look faithful ends and actual faithfulness begins. You know the language of sin and repentance; you can name your type, and people call you disciplined, loyal, even authentic, yet underneath sits an exhaustion that trying harder has never touched. The mask you put on to stay approved and protected has been on so long that it now feels like your face. Chuck DeGroat returns with twenty-five years of sitting with pastors, leaders, and couples whose defenses have hardened into narcissism, which he insists runs on a spectrum that includes more of us than we'd admit. About Chuck DeGroat Chuck DeGroat is a professor of pastoral care and Christian spirituality at Western Theological Seminary in Holland, Michigan, where he also serves as founding executive director of the clinical mental health counseling program. A licensed therapist, spiritual director, and former pastor in Orlando and San Francisco, he has spent more than two decades counseling pastors and leaders on the narcissistic spectrum and those wounded by them, work he wrote about in When Narcissism Comes to Church. His newest book is Who You're Becoming: The Slow and Courageous Work of Cultivating Character in a Narcissistic Age. 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.
Sitting under preaching every Sunday is not the same as knowing the Scriptures well enough to recognize when you are being led somewhere the text never meant to take you. A sermon that never confronts your sin can feel like grace, until one day you realize that your discernment and your hunger for the Lord have drifted off course a few degrees at a time. The uncomfortable question is not whether false teaching exists, but whether you would recognize it if you heard it. Philip Anthony Mitchell, founder and lead pastor of 2819 Church in Atlanta, joins me for an urgent conversation about the state of the American church. About Philip Anthony Mitchell Philip Anthony Mitchell is the founder and lead pastor of 2819 Church in Atlanta, Georgia, a congregation named for the Great Commission in Matthew 28:19, and he is known for bold, Scripture-anchored gospel proclamation and an unflinching call to spiritual maturity. He has been married to Lena since 2004, and together they have four children. His debut book, Contend, draws on the letter of Jude to call believers to stand for biblical truth in the culture while fighting for faith in the hidden battles of the heart. 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.
Dr. Les Parrott joins me for a conversation that refuses the comfort of our cultural vocabulary. As a clinical psychologist, Les insists that pain isn't the same thing as trauma, and that the difference lies in what an experience has done to your capacity to feel safe and function, not in how much it hurt. From there we press into love itself, because rescuing people from the consequences of their choices can feel like compassion while keeping them small. About Dr. Les Parrott Dr. Les Parrott is a clinical psychologist and, with his wife, Dr. Leslie Parrott, a #1 New York Times bestselling author and cofounder of the Center for Relationship Development at Seattle Pacific University. He created the Save Your Marriage Before It Starts (SYMBIS) Assessment, a premarital tool used by counselors around the world, and has given his career to helping people build healthy relationships. His newest book with Leslie, The One Year Positive Mental Health Devotional (Tyndale, October 2026), pairs biblical truth with psychological insight for anyone who has ever been kept awake by an anxious mind. 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 become very good at being seen. You know how to read a room, how to offer just enough of your story to seem open while keeping the deepest thing safely out of view, how to hand the world a competent, admirable version of yourself. And still, underneath the feed and the applause and the performance you have perfected, there is an ache you can no longer explain away, because you are surrounded and you are not known. In this conversation, Ian Simkins joins me to name the quiet distance between the platform and the table, and to expose how much of our exhaustion is simply the cost of maintaining an image our bodies, our nervous systems, and our spirits were never built to sustain. About Ian Simkins Ian Simkins is the lead pastor of The Bridge Church just outside Nashville, Tennessee, where he lives with his wife, Katie, and their three sons. Shaped for years in ministry in the Chicagoland area before moving his family to Middle Tennessee, he writes and teaches out of the actual life of a local church rather than from theory. His new book, Every Table an Altar: Reclaiming Connection in a World of Division, Distraction, and Loneliness (Zondervan), was born from that community, and it makes the case that the antidote to our disconnection is not another program or platform but the ordinary, sacred practice of gathering at a table. 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.
Jonathan Eckert has spent more than three decades watching what happens to people, young and old, when comfort becomes the organizing principle of a life, and in this conversation he draws the line most of us have blurred: the line between happiness that is circumstantial, self-focused, and fleeting, and the joy the Lord actually offers, which is not the absence of struggle but the very fuel that allows us to struggle well. We talk about the frictionless world we have engineered for ourselves and what it is quietly costing our capacity to be human, about why Scripture rarely lets joy stand apart from trial, and about what it means to count it all joy when we meet trials of various kinds, not because the trial is good, but because of what the Lord forms in us when we refuse to run from it.