This week on Deeper Conversations, we’re in Ecclesiastes 7:5-7 with special guest Sue Brown, a longtime member of The Crossing. We discuss what it means to finish well—to walk faithfully through every season and stay true to God’s calling until the very end.

Why does Solomon say it’s better to go to a house of mourning than a house of feasting? In this episode of Deeper Conversations, we wrestle with what it means to live wisely, grieve deeply, and value what truly lasts.

Grief and reflection aren’t pleasant—but they grow us. Join the conversation as we explore how sorrow can refine the soul more than comfort ever could.

We chase more — more success, more comfort, more control. But Solomon says even when we get it, it can still feel empty. In this episode of Deeper Conversations, we unpack Ecclesiastes 6 and talk about why satisfaction isn’t found in what we possess but in who we trust.

In this episode, Pastor Lee Brewer and Pastor Matt Bennett walk through Ecclesiastes 5, focusing on the final verse — “God keeps him occupied with joy in his heart.”

They explore how a life centered on God brings peace and contentment even in the midst of work, wealth, and worry. Join the conversation as we rediscover the joy that only comes from Him.

In this episode of Deeper Conversations, Pastors Lee Brewer and Matt Bennett explore Ecclesiastes 4. Together, they reflect on what it means to live with one hand full and contentment rather than striving endlessly for more. The discussion also highlights the God-given gift of friends and community, and how they help us live with purpose and joy.

Pastor Lee Brewer and Pastor Matt Bennett dive into one of the most well-known passages in Scripture—Ecclesiastes chapter 3. Together they unpack what it means that there is a time for everything, and how this chapter reminds us that control is really just an illusion. We can’t dictate every season of life, but we can trust the One who holds time in His hands.

In this episode, we walk through Ecclesiastes 2, where Solomon explores the pursuit of pleasure, work, and wisdom—and finds them empty without God. What does that mean for us today? How do we find meaning that lasts?

Listen now and join the conversation.

In this episode of Deeper Conversations, Lee Brewer and Pastor Matt Bennett walk through the parable of the Prodigal Son. True repentance isn’t just feeling bad for yourself—it’s recognizing your wrong and turning back. And from the Father’s perspective, relationship always outweighs the offense.

Pastor Lee and Pastor Matt dive into Luke 15 to explore the parable of the lost sheep and the parable of the lost coin. Together, they unpack what these stories reveal about God’s relentless pursuit, His joy in finding the lost, and how these truths challenge the way we see and love others.

In this episode of Deeper Conversations, Matt Bennett and Lee Brewer sit down to unpack what might be the most unexpected business model ever: Jesus’. As the religious elite grumbled, Jesus welcomed sinners, tax collectors, and outcasts—and then trusted them to carry His message. Drawing from Luke 15, this conversation lays the framework for the next three parables in the sermon series, exploring how grace—not status—is the real qualification for Kingdom work.