Stay True with Madison Prewett Troutt

Episode: Trusting God When It Still Hurts with Tim Timberlake

Release Date: October 20, 2025
Host: Madison Prewett Troutt
Guests: Tim Timberlake (pastor, author), Grant Trout

Overview

This heartful episode centers on the powerful theme of trusting God through pain, disappointment, and long seasons of unanswered prayers. Madison ("Maddie") Pruitt Trout and her husband Grant host Pastor Tim Timberlake, who shares his profound family legacy, testimony, and the story behind his new book The Bumpy Road to Better. Together, they get real about faith "in the middle" of messiness—why embracing our struggles, pain, and questions can be an act of worship and hope.

Tim’s honest, vulnerable storytelling offers wisdom for anyone wrestling with their faith, dealing with setbacks, or feeling unseen in their suffering. The conversation is rich with spiritual insight, practical encouragement, and reminders of God's constant presence, even when the road is bumpy.

Key Discussion Points & Insights

1. Tim Timberlake’s Family Legacy and Personal Journey

[06:35–14:43]

• Tim shares the profound impact of his family’s faith heritage, beginning with his grandfather’s transformation from a sharecropper to a church planter after a miraculous healing in response to prayer.
• He details his father's battle with throat cancer, Tim’s own anger and rebellion towards God as a youth, and ultimately, his supernatural call into ministry—a prophetic dream of blood on his hands, which exactly matched a dream his father had years before.
• The importance of documenting legacy: Tim treasures his late father’s saved sermon notebooks (the only possessions salvaged from a house fire) and leaves audio and written messages for his own son:

  “I want him to still hear my voice, hear my perspective, hear my fathering, my approach to Scripture, so that I can lead him even when I’m physically not here.” —Tim ([14:00])

Notable Moment:

• The generational dream: Both Tim and his father were called to ministry through the same vivid vision.

2. Meeting His Wife & Their Story of Resilience

[19:10–24:53]

• Tim met his wife in New York, both drawn together by divine timing amidst her devastating brain injury and recovery.

  “She was a double bachelor’s, Master’s, the art director for the largest sports marketing agency in America … [after her accident] was knocked back to a second grade learning level.” —Tim

• He narrates their patient, faith-filled courtship—deliberately waiting for God’s timing, supporting her through ongoing struggles, and FaceTiming every day until marriage.
• Grant remarks on how this personal bumpy road gives depth to Tim’s new book:

  “Just hearing that part of your story makes this book title super real, for sure.” —Grant ([25:00])

3. The Painful Road of Leadership & The Message of "Bumpy Road to Better"

[25:35–30:50]; [34:44–38:01]

• Tim describes leading the family church at age 20, facing skepticism, rejection, and the pain of leading people who "don't want to be led by you."
• He frames humility as the “fruit of pain”—explaining that the deepest attributes of God are often learned in valleys, not on the mountaintop:

  “Humility, for me, is the fruit of pain. It comes as a result of stewarding hardship, stewarding pain, stewarding breakdowns ... very well.” —Tim ([26:36])

• The book is a “real-time journal” through the middle of suffering—a rarity in Christian leadership literature.
• On God’s trust:

  “It’s one thing to be trusted with blessings. It’s something completely different to be trusted with pain.” —Tim ([27:40]) “Have you considered my servant?... not for blessings... for pain. Because God knew that he trusts me enough... that even in hardship, he won’t turn his back on me.” —Tim ([28:08])

4. Wrestling Honestly with God & Navigating Doubt

[34:44–39:47]

• Tim and Maddie discuss the reality of faith and doubt coexisting for sincere believers, especially leaders.
• Tim encourages honesty in bringing questions and frustration to God, insisting that true faith walks “hand in hand with my doubt to the feet of Jesus.”

  “Wrestling is one of the greatest signs that we have not been overtaken by the enemy. When there is no more fight ... that means we’ve given up. So, just like Jacob did in the Old Testament, wrestle with it until God changes the way you walk.” —Tim ([35:23])

• The opposite of faith is not doubt, but what we see:

  “The opposite of faith is what we see, because it does not take faith to see what we already see.” —Tim ([37:13])

• He shares practical advice for speaking God’s Word louder than the voices of doubt.

5. The Interplay of Hope and Disappointment

[42:19–45:50]

• Candid reflections on how hope and frustration can coexist for the believer.
• Tim likens spiritual endurance to going to the gym—you suffer through temporary pain for the image of who you’ll become. In spiritual life, pain is meant to mold us:

  “If God does not remove it, if God does not change it, it’s because God is changing you and he’s molding you and shaping you.” —Tim ([44:05])

• “Don’t deliver me until you’ve developed me”: a prayer for suffering to finish its good work (brought up by Grant, [42:02]).
• Tim’s mature approach:

  “I don’t want pain to leave my life until it produces the fruit it’s supposed to produce...” ([45:00])

6. Wisdom for the Church & Dealing with Division

[47:15–51:32]

• Tim addresses confusion and division in today’s culture, calling leaders and believers back to the foundational call of unity in Acts 4:32:

  “There’s a difference between agreement and unity. We don’t have to agree on everything to be unified ... let’s put a priority on what does Jesus want for us right now.” —Tim ([48:00], [49:45])

• On loving those who are hard to love:

  “When God wants to bless you, he sends you people. When the devil wants to curse you, he sends you people...” —Tim ([51:32])

• Guarding your heart from public opinion and focusing on the love and opinions of those closest to you.

7. Practicing Humility and Forgiveness in Real Time

[55:53–64:57]

• Tim’s real-time struggle: Currently enduring three lawsuits and online attacks, Tim shares how the Holy Spirit is instructing him to “be silent” instead of defending himself, trusting God to be his defender.
• He emphasizes keeping a pure heart, daily naming and processing any anger or bitterness, and “not going to sleep frustrated or angry.”

  “Being patient enough to see God work through the things that he’s working through in a way that honors Him is one of the greatest things I could ever do in a season where I’m like, ‘okay God, like, this is crazy.’” —Tim ([56:20])

• On forgiving enemies:

  “God says, nope, I want you to pray for them. I want you to pray that I will bless them. … Pray it again, and I want you to mean it this time.” —Tim ([63:24]) “We judge people based upon what they do and judge ourselves based off what we intended to do.” —Tim ([64:23])

• The daily cycle: offering grace, giving the Word rather than opinion, and remembering that “Each scar is a testimony that what tried to kill me did not succeed, but God prevailed.” ([30:24])

Notable Quotes & Moments

• On Pain and Stewardship:

  “One of the greatest things that God could ever entrust us with is pain. And if we steward pain well, it opens up doors for us to steward the various seasons of joy, peace, happiness well.” —Tim ([28:05])

• On Real Faith:

  “If my faith is alive, then my faith walks with my doubt hand in hand to the feet of Jesus.” —Tim ([35:23])

• On Spiritual Endurance:

  “I don’t want pain to leave my life until it produces the fruit it’s supposed to produce … because every test that we take is only supposed to be taken one time. The only time we have to retake it is if we fail.” —Tim ([45:00])

• On Forgiveness:

  “Don’t just respond like me, react like me. When it’s fresh, react like me. When it’s real time, react like me. ... Pray that I will bless them. ... Pray it again, and I want you to mean it this time.” —Tim ([62:40])

• On Legacy:

  “Write the journey you’re on and write it to your kids, because one day they’ll find them.” —Tim ([14:00])

Timestamped Key Segments

• [06:35–14:43]: Tim’s family history; the generational dream and legacy
• [19:10–24:53]: Love story and resilience through his wife’s illness and recovery
• [25:35–30:50]: Pastoral hardship, spiritual pain, and the roots of humility
• [34:44–39:47]: Wrestling with God, normalizing doubt, and spiritual authenticity
• [42:02]: Grant’s prayer “Don’t deliver me until you’ve developed me.”
• [43:03–45:50]: Can hope and disappointment coexist? Joy in pain
• [47:15–51:32]: Unity in the church, loving difficult people
• [55:53–64:57]: Real-time example of humility under attack, forgiveness practices
• [66:49–68:27]: Tim’s closing prayer for listeners

Final Takeaways

• Suffering is not wasted: When stewarded in faith, pain does Kingdom work—molding, pruning, and producing fruit in the believer.
• God wants our honesty: Doubt, frustration, and wrestling can be an act of faith when brought sincerely to Jesus.
• Spiritual disciplines matter: Staying rooted in scripture, prayer, and worship are “basic,” but supernatural in their power to transform and sustain.
• Unity, humility, and love are non-negotiables—especially in a divided world.
• Leave a legacy: Share your faith and struggles authentically for those who will come after you.

"Although the road may be bumpy, it is leading you to better. And better does not always mean that it will be the same as someone else’s journey, but it does mean that it is better than where you were."
—Tim Timberlake ([64:58])