Holy Heartbreak Podcast

by Ryan Dawn Holland

Season 2

Hope That Hurts vs. Hope That Heals: Discovering God’s True Design For an Anchoring Hope w/ Ida Benson-Jaja (Part 2)

In this episode, Ryan Dawn Holland and Ida Benson-Jaja (owner of @homekitchenatl) delve into the complexities of hope, exploring its biblical foundations and personal implications. They discuss the stories of Joseph and Abraham, emphasizing the importance of maintaining hope against all odds. The conversation highlights the significance of perspective in understanding hope and the necessity of waiting with expectancy. They also touch on the emotional struggles associated with deferred hope and the healing that can come from trusting in God's timing and character. Takeaways Hope can sometimes hurt, but it's essential for growth. Biblical figures like Joseph exemplify hope against all odds. The concept of being 'prisoners of hope' encourages resilience. Shifting perspective can transform feelings of hopelessness. Waiting with expectancy is crucial in the journey of faith. God's timing is often different from our expectations. Hope deferred can lead to heartache, but it can also lead to deeper faith. Understanding God's character can renew our hope. The journey of waiting can prepare us for future blessings. Patience is a virtue that can lead to healing and fulfillment.

S2 · E11

Sep 13, 2025

41:57

Hope That Hurts vs. Hope That Heals: Discovering God’s True Design For an Anchoring Hope w/ Ida Benson-Jaja (Part 1)

In this episode of the Holy Heartbreak podcast, host Ryan Dawn Holland and guest Ida Benson-Jaja delve into the profound themes of hope, faith, and perseverance. Through heartfelt discussions and personal stories, they explore the complexities of understanding God's character and the promises He makes to His followers. Join them as they navigate the challenges of hope deferred, the strength found in God's covenant, and the transformative power of trusting in His divine timing. Whether you're seeking encouragement or a deeper spiritual insight, this episode offers a thoughtful exploration of faith in the face of life's trials.

S2 · E10

Sep 4, 2025

48:49

Do Not Worry? Unpacking the Bible on Anxiety

In this episode, Ryan Dawn Holland and Amber Ginter Johnson dive into the intersection of faith and mental health. Amber vulnerably shares her own journey with anxiety within a Christian context, offering wisdom on what it looks like to hold both faith and struggle at the same time. Together they explore: ✨ The nuances of anxiety and the importance of naming our emotions without shame ✨ How prayer and community can support mental wellness ✨ What passages like “Do not worry” really mean ✨ God's intentions for us in our fears and worries The conversation ends with a heartfelt prayer for listeners, reminding us that it’s okay to seek help—and that God meets us with compassion right where we are. For more from Amber, follow her on Instagram ⁠@amberginterauthor⁠ or visit ⁠amberginter.com⁠.

S2 · E9

Aug 20, 2025

49:57

Is God Really Enough? Reimagining Singleness, Calling, and the Ache of Loneliness w/ Pieter L. Valk

This week, I’m joined by ⁠@pieterlvalk⁠, licensed counselor, ministry leader, and cofounder of a modern Christian monastery, for a conversation that challenges what we’ve been taught about singleness. We talk about: 💬 The difference between common and vocational singleness 🏠 Why celibacy doesn’t have to mean isolation 🧭 How to discern your calling without rushing it 🤝 Practical ways to build true community as a single Christian 👨‍💻 The difference between loneliness and aloneness 🙏 And if God alone is really enough If you’ve ever felt alone in your singleness, unsure of your future, or just hungry for deeper connection—this one’s for you. You can find more work from Pieter L. Volk by following him on instagram @pieterlvalk, checking out his ⁠resource links⁠, or following @nashvillefamilyofbrothers. To support Holy Heartbreak Podcast, you can leave us a tip ⁠here⁠.

S2 · E8

Aug 5, 2025

45:28

Desire, Delay, and Denial: What Waiting Reveals About our Devotion

In this solo episode, Ryan Dawn takes listeners into the story of Abraham — not the highlight reel, but the quiet, difficult years of waiting between promise and fulfillment. With honesty and depth, she explores how desire, when unmet or delayed, can shape our spiritual lives — sometimes deepening our devotion, other times becoming distorted into idols. Drawing from biblical narrative and personal reflection, Ryan shares how God uses seasons of delay to transform us — not just our circumstances. She unpacks why we often want "Abraham results" without "Abraham waiting," and how surrendering control can lead to deeper intimacy with God. If you’ve ever felt stuck in between what God spoke and what you're actually seeing — this episode is a reminder that your waiting isn’t wasted. ✨ Topics covered: Why God gives promises, not plans The difference between desire and idolatry How control can quietly take over our faith Building altars to God instead of to our wants What our waiting reveals about our hearts Scripture-rich, deeply reflective, and honest — this is for anyone walking through a long season of longing.

S2 · E7

Jul 24, 2025

24:45

When Suffering Lingers: Keeping Faith in God's Goodness When the Healing Doesn't Come w/ Brenna Blain

What if the healing you’ve begged God for never comes? In this vulnerable conversation, Ryan Dawn sits down with author and speaker Brenna Blain (@bunonmyhead) to talk about suffering, mental health, and what it looks like to stay faithful when your prayers aren't answered (at least the way you'd expect). Brenna shares openly about living with bipolar disorder, the pain of unanswered prayers, and the pressure to perform spiritual perfection in Christian spaces. Together, they unpack: Why the Church often doesn’t know what to do with real suffering How prosperity gospel lite sneaks into our expectations The tension of preaching while struggling Why vulnerability isn’t a liability—it's protection Finding God in slow, quiet, ordinary healing The difference between hoping for rescue and being sustained by presence This episode is for anyone who’s still hurting and still here. For the ones who keep showing up, not because it’s easy—but because they still believe God is who He says He is. 🎧 Listen wherever you get your podcasts 📘 Grab Brenna’s book ⁠Can I Say That? How Unsafe Questions Lead Us to The Real God⁠ 🔗 Follow her at ⁠@bunonmyhead⁠ 🎧 Hear more of her story on ⁠With The Perrys⁠ and ⁠The Deep End With Lecrae⁠

S2 · E6

Jul 16, 2025

45:26

Therapist or Spiritual Mentor—Do I Need Both? Maturing Spiritually Through Trauma, Church Hurt, and Everything In Between w/ Kyle Spears

In this episode of Holy Heartbreak Podcast, Ryan Dawn Holland sits down with therapist, podcaster, and spiritual mentor Kyle Spears to talk about seeking spiritual maturity both in and out of the church. Together, they unpack the tension between needing therapy and spiritual guidance. This conversation gets real about: When scripture gets weaponized What emotionally healthy mentorship really looks like (and how to be a good advisor) Why trauma-informed discipleship is essential How to find a safe spiritual mentor who won’t try to “fix” you And why doing the work—in therapy and in faith—is a vital part of maturing in Christ Whether you’ve been burned by bad advice, manipulated with Bible verses, or just want to grow into a healthier spiritual life, this episode will help you start unpacking what healing can actually look like. 🔗 Check out Kyle Spears' podcast, Truth, Trauma, Theology → ⁠https://truthtraumatheology.podbean.com/⁠ (or wherever you get your podcasts!!)

S2 · E5

Jul 8, 2025

1:00:17

Obadiah's Warning: How Pride Blinds Us to Injustice-- And How God's Wrath Reveals His Love w/ Matt Walker Thrift

In this episode, Ryan Dawn sits down with Pastor and author Matt Walker Thrift to dive deep into the overlooked but fiery book of Obadiah. What starts as a story about an ancient nation’s downfall becomes a mirror—showing us what pride, silence, and spiritual complacency can still do today. Together, they explore how Edom’s pride became the gateway to injustice, how unchecked ego leads to complicity, and why God’s wrath is actually a radical act of love: A defense of the oppressed A warning to all of us who might become the oppressor This conversation takes a sharp, honest look at fallen leadership, spiritual pride, and the danger of standing by instead of speaking up—but it doesn’t leave us there. It also offers the hope of humility, community, and a God who invites us to do better. If you’ve ever wrestled with injustice, spiritual disillusionment, or your own complicity in silence, this one’s for you. For more, pre-order Pastor Matt Walker Thrift's book “Enemies of the Heart: What the Forgotten Prophet Teaches us About Bitterness, Betrayal, and God’s Justice” ⁠here⁠.

S2 · E4

Jul 1, 2025

58:23

This Wasn't the Plan: When You Pray for a Miracle and Get... Character Development w/ Liz Sevigny (@thebald_mom)

In this heartfelt conversation, Liz Sevigny (@thebald_mom) shares her journey with alopecia, discussing the emotional and spiritual challenges she has faced. From her initial diagnosis at age 12 to the profound impact of hair loss on her self-image and faith, Liz opens up about her struggles and the turning points that led her to share her story online. She emphasizes the importance of community support, vulnerability, and finding confidence beyond physical appearance. Liz also reflects on her relationship with God, and how she processed unanswered prayers and a lack of "physical healing."

S2 · E3

Jun 24, 2025

59:43

You Are Not Behind: Ditching Arbitrary Timelines & Embracing Where You Are w/ Meghan Ryan Asbury

Ever feel like everyone else is living your dream life while you're just... trying to hold it together? Same. In this episode of Holy Heartbreak, Ryan Dawn Holland sits down with Meghan Ryan Asbury (@meghanryanasbury), author of You Are Not Behind, to talk about what it means to live in the tension of unmet expectations, delayed dreams, and that “grass is greener” pressure that constantly whispers: “You’re falling behind.” Together they dive into: Feeling left out of life’s timeline What true contentment actually looks like How to hold gratitude without faking positivity Grieving what never happened (and maybe never will) Processing the pain of “dangling carrot” moments with God And why celebrating others doesn’t mean you’re losing If you’re tired of “waiting well,” if comparison has worn you down, or if you're wondering where God is in the middle of your “not yet”—this conversation is a deep breath and a needed reminder: you are not behind. 🎧 Listen wherever you get your podcasts 📚 Grab Meghan’s book: You Are Not Behind 📲 Follow her at: @meghanryanasbury #youarenotbehind #holyheartbreak #Christianpodcast #spiritualburnout #faithandwaiting #faithandgrief #comparisontrap #hopeandhealing #griefandgratitude

S2 · E2

Jun 17, 2025

46:26

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