Probably Overthinking It

What happens when the shame of your past convinces you that you have no business being the person God is asking you to be?Jackson DeRose is an associate student minister who opens up about shame, spiritual warfare, living with OCD, and so much more.

Houston opens up about the question that changed everything, the difference between happiness and joy, why he speaks Jesus over songwriting sessions, what success looks like, and what it was like to get that call on the day of the Covenant School shooting.This is a conversation about faith that actually costs something, what it means to love your neighbor, and what legacy really looks like for a dad trying to raise young believers. 1:17 – Welcome Houston 4:36 – God Winks 11:41 – Faith Journey 14:23 – The Question 16:59 – Success as an Obstacle to Faith 20:49 – Happiness vs. Joy 24:04 – Authenticity 28:20 – "Me and Jesus" 36:05 – Covenant School Shooting 40:25 – Prayer Vigil 45:43 – Double Rainbow 47:10 – Discernment & Prayer 50:01 – Benefit Concert 51:50 – Spiritual Gifts 58:52 – Spiritual Warfare 1:03:03 – Prayer Journal 1:05:02 – What is God Teaching Us? 1:09:07 – Transition in Parenting 1:14:00 – Disaster ReliefMentionsShawn Ryan Show #285 - Father Chad Ripperger: https://youtu.be/I2p_cfipbEw?si=XF6aK-DX3a2ZdIDiMentionsRick Warren's Daily Hope: https://www.pastorrick.com/"Barefoot Blue Jean Night" - Jake Owen: https://open.spotify.com/track/3ts6xK5GzfMAAriT9AIBmP?si=59d673d31ab5435b"Believe" - Lenny Kravitz: https://open.spotify.com/track/6x9t21Gl6bRhOrgigur7wK?si=8dd55b9bd50c469e#ProbablyOverthinkingIt#ChristianPodcast#FindingIdentityInChrist#FaithInTheValley

What happens when your career stalls, your ambitions fall apart, and the things that once defined you no longer work?In this episode, Kyle and Bo sit down with their first guest, Jay Billington, to talk about prolonged job loss, failed ventures, and the slow, uncomfortable work God does in the valley.Jay shares honestly about a season of unemployment, misplaced identity in achievement, being angry with God, and learning not to rush past what God may be forming through periods of struggle. In this episode, we talk about:Job loss and identity when career and ambition fall awayWhy the valley matters and why we often try to escape it too quicklyBeing honest with God about anger, disappointment, and confusionLetting go of self-promotion and learning to serve others with humilityHow success can quietly become an obstacle to faithObedience, attention, and what actually has eternal valueProbably Overthinking It is a podcast about ordinary people sharing stories of their walk with Jesus. This conversation is not polished or performative. It is honest, reflective, and rooted in the belief that God often works most clearly through brokenness.If this episode resonates with you, please consider subscribing and sharing it with someone who may be walking through their own valley.00:00:00 Opening – Connection & Authentic Faith00:00:38 Serving God Where You Are00:03:55 Army Background & New York Transition00:05:40 New York Bible Study (CEOs vs Normal People)00:07:42 Being Mad at God00:10:00 Army as More Than a Career00:12:00 Advice for the Jobless00:15:15 God Sees You in the Valley00:20:45 Trophies & Motivation00:24:25 If It’s About Me, I’m Not Interested00:27:20 God Will Get the Message Through00:31:30 Where Did That Thought Come From?00:40:00 Opposite of the Beatitudes00:41:30 God’s Better Way00:42:30 When Do You Feel Closest to God?00:44:00 Frontier Son, Music, and Community00:51:45 Music Draws Out Emotion00:56:00 What Is God Teaching You Now?01:00:00 What Deserves Your Attention?01:01:10 What Has No Eternal Value?01:04:00 Obedience01:08:30 Recognizing What Christ Has DoneMentions- Frontier Son - Frontier Son: https://open.spotify.com/album/0DY13cqw2xKGoS07tjQALn?si=nK0OXDDWQh6mnwT_7szlHw- Shofar - https://en.wikipedia.org/wiki/Shofar- Brother Yun - "The Heavenly Man” - https://amzn.to/4tvz1yb- A.W. Tozer - "The Pursuit of God" - https://amzn.to/4rUrmrw- Gospel of Matthew: https://www.biblegateway.com/passage/?search=Matthew%201&version=CSB- Quote from Alice Walker, author of "The Color Purple" - https://en.wikipedia.org/wiki/Alice_Walker#ProbablyOverthinkingIt#ChristianPodcast#FindingIdentityInChrist#FaithInTheValley

We Had to Talk.In this first episode of Probably Overthinking It, Kyle and Bo share an honest, deeply personal conversation about faith, surrender, addiction, near-death experiences, and what it means to trust God when the end feels near.In this episode, we talk about:Moving from achievement to surrenderA father’s letter written as he sensed the end was comingAddiction and silent strugglesNear-death experiences and discernmentPlanting seeds of faith and trusting the Holy SpiritProbably Overthinking It is a podcast about ordinary people sharing honest stories of their walk with Jesus — the questions, the doubts, and the hope.MentionsShawn Ryan Show – John Burkehttps://youtu.be/tH3eVf0C1QYJohn Burke – Imagine the God of Heavenhttps://amzn.to/3M3cZC4Frontier Son – Frontier Sonhttps://open.spotify.com/album/0DY13cqw2xKGoS07tjQALnGillette Foamy Shave Gelhttps://amzn.to/4q07CBNC. S. Lewis – Mere Christianityhttps://amzn.to/4sYF2DhA. W. Tozer – The Pursuit of Godhttps://amzn.to/3YSFu8uDietrich Bonhoeffer – The Cost of Discipleshiphttps://amzn.to/3Ny7qw1NT Wright on Blurry Creatureshttps://open.spotify.com/episode/02NsZd1B7p8EDOfheOVKwwBible passages referenced: Matthew, Hebrews, IsaiahBible Cross-References Visualizationhttps://www.chrisharrison.net/index.php/visualizations/BibleVizD. A. Carson – The Gospel According to John (The Pillar New Testament Commentary)https://amzn.to/3YXaK6bMatt Dinniman – Dungeon Crawler Carlhttps://amzn.to/46bjbPbChris Williamson – “Attention Is More Important Than Time”https://www.youtube.com/shorts/FqcZSo9n_x8