Free To Fail | Ryan Dunlevy | 09.20.26

Sep 20, 2026

Devotional

Day 1: When Sinking Hands Still Find Grace

Failure often leaves us thrashing in shame’s wake, convinced we’ve sunk beyond rescue. Peter’s waterlogged cry—“Lord, save me!”—mirrors our own desperation when risks collapse into humiliation. Yet Jesus’ hand breaches the chaos before the plea finishes. His grip isn’t reluctant or delayed but immediate, unbothered by spray or splutter. Rescue isn’t contingent on perfect faith but on His nearness in the faltering. Even mid-sink, we’re never outside the reach of grace. [36:23]

“Immediately Jesus reached out his hand and caught him. ‘You have so little faith,’ Jesus said. ‘Why did you doubt?’” (Matthew 14:31, NLT)

Reflection: When has a failure made you feel alone in the aftermath? How might Jesus’ immediate response to Peter reshape your view of His presence in your own sinking moments?

Day 2: Failure as the Playground’s Teaching Rail

A child’s aborted swing across monkey bars reveals how fear often overrides capability. Jesus’ question to Peter—“Why did you doubt?”—is less rebuke and more a coach’s nudge to review the tape. Every botched attempt holds data: where focus slipped, where strength faltered, where distractions roared. Failure becomes training footage when we let it replay with curiosity rather than shame. What did the wind teach Peter about his faith’s blind spots? [39:01]

“Let perseverance finish its work so that you may be mature and complete, not lacking anything.” (James 1:4, NLT)

Reflection: Identify a recent failure. What practical lesson does it offer about your habits, assumptions, or needs that success might have hidden?

Day 3: Renamed After the Storm

Peter crawled back into the boat drenched in failure’s residue. Yet two chapters later, Jesus crowns him “the rock”—a name mocking his sinkable nature. Identity isn’t forged in flawless performance but in Christ’s stubborn vision of who we’re becoming. Our stories include failures, but they’re footnotes to the title He gives: beloved, chosen, His. The disciple who sank became the apostle who anchored thousands. [43:14]

“Now I say to you that you are Peter (which means ‘rock’), and upon this rock I will build my church.” (Matthew 16:18, NLT)

Reflection: What failure have you allowed to name you? How might Jesus’ renaming of Peter challenge that self-imposed label?

Day 4: Hersheypark Rides and Second Chances

Backing out of a thrill ride leaves regret thicker than fear. The Tidal Force became a tutor: avoidance steals joy’s splash. Peter’s second chances—preaching at Pentecost, baptizing Gentiles—prove failure isn’t fate. Every sunk step trains courage for the next risk. What “rides” have you avoided since a prior fall? Love’s opportunities often wait past the turnstile of pride. [40:42]

“Forget the former things; do not dwell on the past. See, I am doing a new thing!” (Isaiah 43:18–19, NLT)

Reflection: Where has past failure made you over-cautious? What “ride” might God be inviting you to retry with His grip as your safety bar?

Day 5: Risking the Cardboard Sign

Hustling unused tickets outside the arena felt degrading, yet humiliation’s sting fades faster than regret’s ache. Jesus’ question lingers: What loving act have you avoided to dodge awkwardness? Texting the estranged friend, apologizing unprompted, volunteering despite imposter syndrome—these are today’s water-walks. Fear says, “Protect yourself.” Love asks, “Who might drown if you don’t step out?” [50:41]

“There is no fear in love. But perfect love drives out fear.” (1 John 4:18, NLT)

Reflection: What specific loving risk have you sidelined due to fear of failure? How might embracing Jesus’ non-abandoning presence free you to attempt it this week?

Sermon Summary

Failure has a way of sticking, especially when embarrassment, shame, and fear get tied to a moment that went badly. The fear of failure can turn one bad experience into a story people tell themselves for years: “I’m bad at this,” “I don’t have what it takes,” or “This is what happens when I put myself out there.” The question, “What would you do if you knew you couldn’t fail?” may help uncover dreams, but real life does not offer no-fail situations. Every dream eventually runs into the real world, where failure is very much on the table.

Matthew 14 shows Peter taking a bold faith risk when Jesus comes walking across the water. Jesus tells the terrified disciples, “Take courage, it is I. Don’t be afraid,” and Peter responds by asking Jesus to call him out of the boat. Peter actually walks on the water for a moment, but the wind and waves become too big in his mind. Fear pulls Peter’s eyes away from Jesus, and Peter begins to sink.

Jesus immediately reaches out His hand and catches Peter. Jesus does not leave Peter in the water because Peter doubted, failed, or needed rescue. Failure may put someone in a hard and vulnerable place, but Jesus does not abandon people there. The hand of Jesus remains present even in the moment when faith feels weak and everything feels humiliating.

Fear of failing again often builds walls meant to keep pain out. Those walls, however, do not only shut out the people who hurt someone. Those walls can keep everybody out, including the people God may be calling someone to love. The safest thing someone can do is not always the most loving thing someone can do. Love requires risks: getting hurt, rejected, embarrassed, inconvenienced, or even failing.

Jesus’ question to Peter, “Why did you doubt?” does not need to be heard as harsh scolding. The question can become an invitation to learn: “You had it. You were so close. If you had kept trusting, you could have kept going.” Failure can shape someone or scar someone. Failure becomes a tool for growth when it provides information instead of becoming something to avoid at all costs.

Peter’s failure was part of his story, but it was not his identity. Jesus later calls Peter the rock on which He will build His church. God’s love is not based on success, reputation, money, or a clean record. A beloved child of God can step out of the boat again because failure does not get the final word.

Key Takeaways

1. Jesus does not abandon failing people. Jesus immediately reached for Peter when Peter began to sink. Failure did not make Peter unreachable, disqualified, or unwanted. Christ’s presence in weakness means that a person’s worst moment is never a place where Jesus refuses to go. [36:23]
2. Safety can keep love from moving. Fear often makes self-protection feel wise, but protecting against every possible awkward moment can shut down compassion. Love sometimes requires stepping into situations that may not work out. A life determined never to be hurt will struggle to love people with the openness Jesus shows. [35:04]
3. Failure can become useful information. Jesus’ words to Peter point beyond shame toward learning. A failed attempt can reveal where fear took over, what needs to grow, and what might be different next time. Things that go wrong can shape a person rather than scar a person when they are brought honestly before God. [39:23]
4. Failure is story, not identity. Peter could have called himself a failure after sinking, yet Jesus named him as someone with a future in God’s church. Identity rests in what Jesus says, not in a person’s latest mistake or another person’s opinion. A beloved child of God does not need success to prove worth. [43:14]
5. Loving risks are worth taking again. Peter failed more than once, but God still used him in huge ways at Pentecost and beyond. Past failure does not cancel God’s plans or remove the possibility of faithful courage. The question becomes not, “How can failure be avoided?” but, “What would happen if failure did not define me?”

## [45:23]

Youtube Chapters

[00:00] - Welcome
[17:44] - A Youth Event That Went Wrong
[21:50] - The Fear of Failing Again
[24:42] - When Self-Protection Blocks Love
[25:44] - Jesus Walks on the Water
[27:43] - Peter Steps Out of the Boat
[29:09] - Peter Sinks and Jesus Catches Him
[33:40] - The Walls Built After Failure
[36:02] - Jesus Does Not Abandon Us
[37:11] - Failure as an Opportunity to Learn
[42:07] - Failure Is Not Your Identity
[45:23] - Taking Loving Risks Again
[46:10] - Questions for Responding
[48:28] - Prayer for Courage and Faith

Bible Study Guide

Bible Reading

Matthew 14:22–33

Immediately after this, Jesus insisted that his disciples get back into the boat and cross to the other side of the lake, while he sent the people home. After sending them home, he went up into the hills by himself to pray. Night fell while he was there alone. Meanwhile, the disciples were in trouble far away from land, for a strong wind had risen, and

Sermon Clips

54s

#CourageousLove

“Sometimes, the safest thing we can do isn't the most loving thing we can do. Love requires us to risk getting hurt, getting rejected, getting embarrassed, getting inconvenienced or even failing. So if we want to be people who don't just believe we should love other people, but actually do love people in bold and courageous ways, we're going to have to refrain, reframe how we view failure. Because the problem isn't that we failed, it's what fear of failing again causes us to do or not do.”

62s

#IdentityInChrist

“Peter's identity wasn't rooted in his failures. It was rooted in what Jesus thought of him. His failure was just part of his story. It was not his identity. And that's true for us too. So what stories are you telling yourself about your failures? Is it possible that God is telling a different story about you than the one you're telling about yourself? Is it possible that God sees you in a much different way than how you see yourself? See, God's love is not dependent upon our success. It's not dependent on how much money we make or what people think of us. It's not dependent on our mistakes or our failures that are in our past.”

36s

#JesusIsWithYou

“Jesus didn't feel like, well, alright, you failed, you screwed this one up, good luck getting back on the boat, you're in there on your own. That's not what Jesus did. Peter failed, he doubted, he literally sank into the water, and Jesus was there to grab him. Do you think Jesus would do any less for us? When we fail, Jesus doesn't walk away from us. He doesn't abandon us. He doesn't leave us on our own.”

40s

#RedemptionStory

“Peter would get out of that boat again. Peter would go on to fail again, but also, he was the person who stood up and gave the sermon that allowed 2,000 people to come to Jesus, Pentecost. Peter was the first one to be able to lead Gentiles to faith in Jesus. God had huge plans for Peter on the other side of some of his biggest failures, and he has the same for you. What amazing story might be on the other side of the failure that you're having a hard time getting past.”

63s

#FaithOverFear

“When we can truly grasp this, when we can truly understand that our identity, the core of our identity, is rooted in what God thinks of us and how much God loves us. When we can get that into our head, it changes what we're willing to do. Because if I don't have to prove myself through success, if failure doesn't define me, if I know that Jesus is still there when I fail, then I don't have to be so afraid of failing. Nobody likes it, nobody wants it, but I don't have to be so afraid of it. And that opens us up to being able to take loving risks, to stop allowing ourselves to be held back by past failures, to stake that step and to get out of that boat again.”

59s

#FailureIsNotFinal

“is to understand that failure is part of your story, it's not your identity. Failure is part of your story, it's not your identity. Because when we fail, it's very, very tempting for us to turn that failure into our identity. When Peter failed in the moment, it would have been easy for him to do that. It would have been easy for him to speak over himself, I failed, and then turn that into I am a failure. This is what happens when I put myself out there. I am always messing up. I am always not getting it right. I am always failing. And when we turn failure into an identity, we become even more afraid to fail again. Because now failure isn't something that happened to us, it says something that proves something about us.”

48s

#LoveWithoutFear

“So like I did with my event failures, we can start intentionally or even unintentionally doing things to avoid failing or avoiding that feeling of failure again. And that's a completely understandable reaction. I mean, who wants to sign up for more pain? Nobody. But what if it's not actually failure, but the things we do to protect ourselves from failure that actually gets in the way of us being able to love people the way Jesus loved people.”

50s

#OpenYourHeart

“And see for us, what often happens to us in these moments is that we start trying to protect ourselves. We put up walls in our lives to try and prevent ourselves from failing and for feeling what we feel after failure. Sometimes we do this consciously and we tell ourselves, well, I'm never gonna let that happen again. Sometimes it just happens as something that just comes into our lives as we're trying to deal with the pain. The problem is that the walls we put up to guard against future hurt and future failure, they keep out not just the people we're experiencing that hurt and failure with, but they keep everyone else out as well.”

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