Podcast Summary: Living on the Border of What Could Have Been
Podcast: Times Square Church - Sermons
Host/Speaker: Pastor Tim Dilena
Date: September 7, 2025
Episode Theme:
Pastor Tim Dilena challenges listeners with a message about moving beyond a life of regret and inaction—what he calls "living on the border of what could have been"—and encourages believers to step fully into faith, purpose, and God’s promises, rather than remaining stuck on the fringe of fulfillment.
Main Theme and Purpose
Pastor Tim Dilena, reflecting on personal and biblical examples, explores the tragedy of living just outside God's best due to fear, indecision, and missed opportunities. Using the story of Israel at the edge of the Promised Land, Tim urges believers not to become content with mere proximity to, but to enter fully into, their God-intended destiny. The episode blends personal vulnerability, biblical exposition, and real-life testimonies to call listeners to decision and movement.
Key Discussion Points and Insights
1. Opening and Global Greeting
- Timestamps: 00:00–05:00
- Pastor Tim welcomes listeners from 71 nations, sets a tone of unity and expectation, and briefly updates on Pastor Carter's health.
2. Personal Regret and Vulnerability
- Timestamps: 05:00–14:00
- Pastor Tim shares a formative question asked by young seminary students:
- “What was your biggest regret at our age?”
- He reveals his regret of not taking full advantage of his access to great Christian leaders in his youth:
“I should have done better with David Wilkerson. I should have done better with Leonard Ravenhill. I should have gotten more. I wish I could go back.” (08:35)
- Encourages young leaders not to “hang on the peripheral with your peers when you could lean in to hear some of the wise, great leaders.”
3. Biblical Foundation: Israel at Kadesh Barnea
- Timestamps: 14:00–25:00
- The Israelites, after being delivered from Egypt, arrived at the border of the Promised Land but ended up wandering for 40 years because of unbelief.
- The key insight:
- “They wandered on the border of their purpose and destiny without ever experiencing it. Folks, this shocked me.” (18:17)
- The entire generation “could probably see at times what they were supposed to do, but never took advantage of it.”
4. Modern Parallels and Pastor Carter's Hospital Witness
- Timestamps: 25:00–33:00
- Testimonies from Pastor Carter’s time in the hospital exemplify living with purpose and ministering even in weakness.
- Notable story: A surgeon confesses to Carter, “I'm not living in sin, but I'm not living the victorious life. And I need help.” (32:00)
- Analogy drawn: Like many Israelites, modern Christians avoid going back to Egypt but also never enter the Promised Land, choosing instead to "live in between."
5. Purpose, Crossroad, and Decision in the Promised Land Story
- Timestamps: 33:00–49:00
- Outlines Israel’s purpose (“He brought us out to bring us in” - 36:30).
- Reviews Numbers 13 and the spy mission—10 spies bring back fear, 2 (Joshua/Caleb) bring back faith.
- “Two men had binoculars. Ten of them couldn't see what God had for them. Maybe this is a day to get the binoculars back on…” (44:42)
- Pastor Tim describes moments when he faced the "10–2 vote" in his own ministry calling.
6. Application: Who Are You Sitting Next To?
- Timestamps: 49:00–54:00
- Interactive challenge:
- “Look at those people. Are they the 10 spies, or do they have a different spirit? Do they push you forward or keep you on the border?” (52:09)
- Importance of surrounding yourself with people of faith and vision.
7. Living with a ‘Heavenly Accent’
- Timestamps: 54:00–01:01:00
- Christians are “seated in heavenly places in Christ Jesus” (Eph 2:6), which should mark their identity and influence how they speak and act.
- “You are in heavenly places and need to speak with that accent every single time. You’re not from here.” (58:18)
- Warning against striving to fit into the world’s culture, when called to live differently.
8. Tozer’s Test and The Value of Truth
- Timestamps: 01:01:00–01:05:00
- Quotes A.W. Tozer:
- “You can always test the quality of religious teaching by the enthusiastic reception it receives from unsaved men... If the natural man receives it enthusiastically, it’s not from the Spirit.”
- Testimony: A hospital nurse says, “I want a church that tells me the truth.” (01:05:00)
9. Parental Choices, Family Faith, and Legacy
- Timestamps: 01:05:00–01:13:00
- Addresses the fear that stepping out in faith will harm your children:
- “They were so afraid the giants would kill their children that they ended up killing them themselves. They killed their faith.” (01:10:43)
- Personal reflection on moving his family for ministry, prioritizing faith over comfort.
- “The greatest heritage to leave to your family is a life of faith.” (01:12:20)
10. The Character of God and His Promises
- Timestamps: 01:13:00–01:16:00
- “You have a God who keeps his word. And we are a people that live by his promises. God never lies.” (01:14:55)
- Rapid-fire listing of scriptural promises on prayer, generosity, waiting, wisdom, honor, submission, and salvation.
11. How to Recover Lost Time—Receiving Jesus into the Boat
- Timestamps: 01:16:00–01:21:00
- Reference to John 6:21: When the disciples received Jesus into the boat, “immediately the boat was at the land to which they were going.”
- “Your life will go where it’s supposed to go” when you invite Jesus fully in. (01:18:41)
- Pastor Carter’s takeaway:
- “I’d rather die on the side of faith than live on the side of unbelief.” (01:19:30)
12. Call to Decision and Action
- Timestamps: 01:21:00–end
- Compels listeners to “leave the neighborhood,” move “from the vicinity,” and step into their purpose.
- Invitation to physically respond by getting out of seats and moving to the altar—symbolizing a move from the border to the promised land.
Notable Quotes & Memorable Moments
-
On Regret:
“I wish I had more stories and more wisdom… but there was more that I missed. There was more I should have leaned in on.” (08:35)
-
On Living on the Border:
“They wandered on the border of their purpose and destiny without ever experiencing it. Folks, this shocked me.” (18:17)
-
On Missed Victory:
“I’m not going back to Egypt, but I’m not going into the promise… you choose this in between…” (32:35)
-
On God’s Promises:
“You have a God who keeps his word. We are people that live by his promises. God never lies.” (01:14:55)
-
On Family and Faith:
“The greatest heritage to leave to your family is a life of faith.” (01:12:20)
“They were so afraid the giants would kill their children that they ended up killing them themselves. They killed their faith.” (01:10:43) -
On Stepping Out in Faith:
“I’d rather die on the side of faith than live on the side of unbelief.” (01:19:30)
Key Segment Timestamps
- Regret and Access to Wisdom: 08:00–10:00
- Israel at the Border: 18:00–19:00
- Pastor Carter’s Testimony: 25:00–33:00
- Spies and Binoculars Analogy: 44:00–46:00
- Peripheral Living Challenge: 52:00–53:00
- Tozer Quote on Truth: 01:01:00–01:04:00
- Family Impact of Decisions: 01:10:00–01:13:00
- Promises of God Listed: 01:14:30–01:16:00
- John 6:21 and Spiritual Acceleration: 01:18:00–01:19:00
- Altar Call and Response: 01:21:00–end
Tone and Language
Pastor Tim speaks with urgency, transparency, humor, and pastoral warmth, seamlessly blending modern anecdotes, personal confessions, and biblical narrative. The style is conversational but direct—inviting listeners to self-examine while infusing hope and clear calls to faith-filled action.
Conclusion
Pastor Tim Dilena’s message, “Living on the Border of What Could Have Been,” is a clarion call not to settle for spiritual mediocrity or live perpetually in the realm of regret and inaction. Drawing on scriptural precedent and personal experience, he urges believers to overcome fear, embrace God’s promises, and make decisions that lead to a full, faith-driven life—both for themselves and their families.
Final Takeaway:
Don’t just stand on the border, gazing at what might be. Get Jesus “in your boat,” trust His promises, and step boldly into the purpose and destiny God has set before you.