What does it mean to live wisely in a world that often feels confusing and out of control? As Holy Trinity begins a new sermon series in the book of Proverbs, Pastor Sully Curtin sits down with Pastor Jon Dennis to explore the distinctive wisdom this book offers for the everyday opportunities and challenges of life.

Together, they discuss wisdom as the “skill of living,” how Proverbs helps us understand the way God has created the world, and why true wisdom ultimately leads us to Christ. They also offer practical ways to engage Proverbs in the months ahead—individually and in community.

In this episode:

• What Proverbs teaches us about the “skill of living”
• How God’s wisdom shapes everyday life
• Practical ways to read, remember, and apply Proverbs

What does it mean to pursue a permanent home for the church while remembering that the church is not a building?

Pastors Sully Curtin and Jon Dennis reflect on Holy Trinity’s long history of gathering in borrowed and rented spaces, the ways God has used our current downtown location to strengthen ministry, and a new property opportunity that could provide a long-term hub for discipleship, training, missions, and hospitality in the heart of Chicago.

Most importantly, they invite the church into Pray 18—30 days of asking God to make His direction clear, open the door if this opportunity is from Him, and close it if it is not. As Holy Trinity considers what may be ahead, this conversation is also a reminder that buildings are ultimately tools for ministry: the church itself is, and always will be, the people of God.

In this episode:

• Why Holy Trinity is exploring permanent space
• The opportunity before us in downtown Chicago
• The vision and invitation behind Pray 18
• Why the church is more than a building

Learn more and join us in prayer at www.Pray18.org

What does it look like for the gospel to shape not only what a church believes, but how its people live together? In this episode of the HTC Roundtable, Sully and Jon continue their conversation about the culture of Holy Trinity Church, exploring what it means for the gospel to be central to our identity, relationships, and life together.

They consider how the good news of Jesus creates a culture marked by grace, hope, and the fruit of the Spirit—and how every member of the church has a part to play in cultivating that kind of community.

In this episode:

• What it means to make the gospel primary rather than simply one belief among many
• How gospel truths shape everyday relationships, conversations, and interactions
• What can quietly undermine a gospel culture—and how we can recognize and address it
• How every member of the church can help cultivate a community shaped by grace and the power of the gospel

What does it mean to truly rest in a culture that prizes productivity and constant activity?

In this episode of the HTC Roundtable, Sully Curtin sits down with Senior Pastor Jon Dennis following his two-month sabbatical to talk about the importance of rest and the rhythms that shape the culture of Holy Trinity Church. Jon reflects on what his time away taught him about our finitude and dependence on God—and why stopping from our work is ultimately an act of trust in God's work.

In this episode:

• Why rest is an essential part of a healthy Christian life
• What Sabbath teaches us about our finitude, dependence on God, and identity in Christ
• How Holy Trinity seeks to cultivate rhythms of work, rest, and relationship
• Practical ways to resist a culture of constant productivity and cultivate habits of rest

In this episode, host Sully Curtin sits down with second-year pastoral resident Jesús Ferro to explore the rich history of partnership between Holy Trinity and the church in Cuba, particularly Nueva Vida in Havana. Jesús shares his story of growing up in Cuba, coming to faith, and serving as a pastor amid one of the most difficult seasons in the country's recent history. Drawing on his family, church, and ministry experience, he offers an inside look at the challenges facing the Cuban people, the remarkable resilience of the Cuban church, and how God continues to advance his kingdom amid hardship.

In this episode

• Jesús' journey from Cuba to pastoral ministry at HTC
• The challenges facing Cuba today and how they shape everyday life
• Why the church in Cuba continues to grow despite hardship and persecution
• How we can pray for, encourage, and partner with our brothers and sisters in Cuba

Join Pastor Sully and Pastor Mike Park, the Associate Pastor at Grace DC, to learn more about how we're seeking to strengthen Theological Partnerships through Chicago churches.

In this episode, Pastor Sully hosts a conversation with Pastor Christian Park on the purpose and value of HTC Community Groups. We believe community happens where you live, and we want to see everyone get plugged into a neighborhood group to grow deeper in their walk with Christ, deeper into community, and invest more deeply in the city. Listen in and join a group this fall!

In this episode, pastors Sully and Jon explore HTC's deep commitment to global missions and the history that shaped our current paradigm. They discuss how the center of global Christianity has dramatically shifted over the last century and introduce our two-pronged approach to missions: sending traditional missionaries while simultaneously building long-term, strategic partnerships with indigenous leaders through an initiative called Neapolis. Tune in to discover how you can participate in the Great Commission today, whether that means crossing cultural boundaries in your own neighborhood, praying for laborers, or preparing to be sent overseas.

• The "Two-Arm" Missions Paradigm: How HTC invests in sending traditional missionaries as well as building direct partnerships with indigenous pastors
• The Vision of Neapolis: Why investing in culturally agile indigenous leaders who "preach, pastor, and plant" is a highly effective way to build strong churches globally
• Everyday Missional Living: Practical ways to engage in cross-cultural missions right here in Chicago, and why future missionaries must first be deeply rooted in a healthy local church

Why does learning matter for the Christian life?

In this opening episode of The Roundtable, pastors Sully Curtin and Jon Dennis explore what it means for the church to be a learning community. They reflect on how following Jesus is a lifelong journey of growing together and how worship, thoughtful conversation, and shared life shape us into mature disciples.

Join us for a conversation about cultivating a learning community that follows Christ with wisdom, humility, and hope in a complex world.