How the Wilderness Forms Men of God

Opening Story

The gravel shifted under our boots as we climbed the last stretch toward the ridge, and I could hear his breathing before I could see his face. It had turned shallow and quick, the kind that tries to hide itself but can’t. He stopped a few steps behind me and bent over, hands on his knees, staring at the ground like it had personally offended him. I didn’t say anything at first. I just stood there, pretending to take in the view so he didn’t feel watched. After a minute, he muttered, almost under his breath, “I don’t think I’m cut out for this.” It wasn’t dramatic. It wasn’t loud. It was matter-of-fact, like he had already decided something about himself that I hadn’t been consulted on.

I walked back down a few steps and stood next to him, not in front of him. “Yeah,” I said, nodding. “It feels like that sometimes.” He glanced up, confused, like he expected correction instead of agreement. We stood there for another moment, both of us catching our breath, the wind cutting across the ridge. Then I added, “But I’ve learned something. Feeling like you’re not cut out for it doesn’t mean you’re not. It just means you’re doing something new.” He didn’t respond, but he didn’t argue either. And that was enough. After a few seconds, he stood up straight, took a deep breath, and started walking again.

In that moment, the mountain wasn’t the real challenge. The story he believed about himself was.

Core Problem

One of the most common mistakes I see in mentoring is how quickly we try to solve the surface problem instead of paying attention to the deeper story underneath it. A boy says he’s tired, so we push him to keep going. A boy says he’s bored, so we try to entertain him. A boy says he’s not good at something, so we rush to prove him wrong. None of those responses are inherently bad, but they often miss what’s actually happening.

What I’ve learned over time is that many of the boys I walk with are not just reacting to the moment in front of them. They are reacting to a lifetime of moments behind them. When a boy says, “I’m not cut out for this,” he’s usually not talking about the hike, the homework, or the situation at hand. He’s revealing a belief that has been quietly forming for years. That belief might have been shaped by absence, by failure, by comparison, or by simply never having someone show him how to do something.

The problem is that if I treat his words as a situational issue, I will offer situational solutions. I might encourage him, push him, or distract him, but I won’t actually address the belief driving his response. And if that belief stays intact, it will show up again and again in different forms. Behavior repeats when belief remains untouched.

Core Principle

The longer I mentor, the more convinced I become of this: A mentor’s role is not to fix a boy’s performance but to reshape the story he believes about himself. Everything else flows from that.

This doesn’t happen through lectures or correction alone. It happens through shared experiences, consistent presence, and moments where a boy begins to see himself differently because someone stayed with him long enough for that shift to occur. It happens when I resist the urge to step in as the expert and instead choose to walk alongside him as a fellow learner.

When I said, “It feels like that sometimes,” I wasn’t trying to lower the bar or excuse the difficulty. I was trying to normalize the experience without reinforcing the lie. There’s a difference between validating feelings and affirming false conclusions. One invites growth; the other locks a boy in place. My goal in that moment was to create just enough space for him to keep going without feeling like he had to become someone else to do it.

Expanded Insight

I’ve noticed that unfamiliar environments have a way of exposing what’s already inside a person. When everything is new, there’s nothing to lean on except what you believe about yourself. That’s why situations like hiking, building something, or trying a new skill can feel disproportionately difficult for boys who haven’t had consistent guidance. It’s not just that they don’t know what to do. It’s that they don’t trust themselves to figure it out.

For many of the boys I mentor, that lack of trust didn’t appear overnight. It was formed slowly, through moments where they were left alone, overlooked, or expected to perform without being shown how. Over time, they learned that it’s safer to disengage than to risk failure. They learned that it’s better to act like you don’t care than to admit you don’t know. They learned that asking for help can feel like exposing a weakness that no one is going to meet with care.

So when they step into something unfamiliar, all of that comes with them. The hike isn’t just a hike. The project isn’t just a project. It becomes a test, not of their ability, but of their identity. And if I don’t recognize that, I will misinterpret their hesitation as laziness or lack of effort, when in reality it’s often self-protection.

Most boys are not avoiding effort. They are avoiding exposure.

That realization has changed the way I approach nearly every interaction. Instead of asking, “How do I get him to try harder?” I’ve started asking, “What is he protecting himself from right now?” That question shifts my posture from correction to curiosity. It slows me down enough to see what’s actually happening.

I’ve also learned that shared difficulty accelerates trust in a way that almost nothing else does. When we’re doing something hard together, the dynamic changes. I’m not just an observer or instructor; I’m a participant. I’m breathing hard too. I’m figuring things out too. I’m not standing at the top calling him up. I’m next to him, taking the same steps.

There’s something powerful about that kind of presence. It communicates, without needing to say it directly, “You’re not alone in this.” And for a boy who has spent most of his life feeling like he has to figure things out on his own, that message lands deeper than almost anything else I could offer.

At the same time, I’ve had to learn the importance of appropriate vulnerability. There’s a temptation to think that mentoring is about having the answers, about being the steady, unshakable presence who always knows what to do. But what I’ve found is that boys don’t need perfection. They need honesty. They need to see what it looks like to be in process.

When I share parts of my own story, not in a way that centers me but in a way that invites connection, it creates permission for them to do the same. It tells them that struggle is not something to hide, but something that can be faced. It reframes growth as something that happens over time, not something you either have or don’t.

This is where mentoring begins to look less like instruction and more like discipleship. Not in a formal sense, but in the way life is shared. Walking together. Learning together. Paying attention to what’s happening beneath the surface. Trusting that growth often comes in small, almost unnoticeable shifts rather than dramatic breakthroughs.

And in those moments, something begins to take root. A boy who once believed he wasn’t capable starts to reconsider. A boy who expected to be left behind starts to notice that someone is still there. A boy who assumed he had to perform to belong starts to experience belonging before performance.

That is where real change begins—not in what he does, but in what he believes is possible.

Here are some practical ways to apply this principal:

1. Create environments where shared challenge is part of the experience.
   One of the most helpful shifts I’ve made is intentionally creating environments where shared challenge is part of the experience. Instead of defaulting to activities that are purely entertaining, I plan moments that require effort, patience, or learning. That might look like a long walk, working on a project together, or trying something neither of us has mastered. The goal is not to overwhelm, but to create a context where growth naturally emerges and where deeper conversations don’t have to be forced.

2. Respond thoughtfully when a boy expresses doubt or frustration.
   I’ve also started being more mindful about how I respond when a boy expresses doubt or frustration. Instead of immediately correcting or encouraging him to push through, I take a moment to acknowledge what he’s feeling without reinforcing the conclusion he’s drawing. Saying something like, “Yeah, this is tough,” can create enough space for him to stay engaged without feeling dismissed or pressured. From there, I can gently redirect the narrative toward possibility rather than limitation.

3. Position yourself as a co-learner rather than an expert.
   Another practice that has made a significant difference is choosing to position myself as a co-learner rather than an expert whenever possible. When I don’t know something, I say it. When I make a mistake, I acknowledge it. Then I invite him into the process of figuring it out together. This doesn’t diminish my role; it strengthens the relationship by removing the pressure to perform and replacing it with an invitation to grow.

4. Use side-by-side settings for meaningful conversations.
   I’ve found that side-by-side settings consistently open the door for more meaningful conversations. Whether we’re driving, walking, or working on something, there’s a natural ease that comes when we’re not sitting face-to-face trying to force a moment. I’ve learned to ask simple, open-ended questions and then allow silence to do its work. Often, the most important things are said in the space that follows, not in the initial question.

5. Gently name what you see beneath the surface.
   There have also been moments where I’ve needed to gently name what I see beneath the surface, especially when patterns begin to emerge. If a boy consistently avoids new situations or shuts down when something feels unfamiliar, I might say something like, “Sometimes this feels harder because no one showed you how before.” The goal is not to label him, but to help him make sense of his experience in a way that reduces shame and opens the door for growth.

6. Anchor these moments in a broader understanding of God.
   Finally, I try to anchor these moments in a broader understanding of who God is and how He meets us. Not through formal teaching, but through simple, honest reflections. I might share something I’m learning, or point out how we’re being sustained in the middle of something difficult. Over time, this helps connect the experience to a larger story, one where he is not alone and where growth is not just possible, but expected.

Conclusion (Bottom Line)

What I’ve come to believe is that mentoring is less about changing behavior and more about walking with someone as their internal story begins to shift. The moments that matter most are often the ones that look ordinary from the outside—a pause on a trail, a quiet comment, a shared challenge—but carry weight because of what they reveal and what they begin to rewrite. When I stay present in those moments, when I resist the urge to fix and instead choose to walk alongside, I create space for something deeper to take root. And over time, that space becomes the place where a boy starts to believe that he is capable, that he belongs, and that he is not alone.

Discussion Questions

1. When a boy expresses doubt or frustration, how do I typically respond, and what might that reveal about what I believe my role as a mentor is?

2. Where in my current mentoring relationships could I intentionally introduce a shared challenge that might create space for deeper growth and connection?