The Dangerous Outlaw
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Crossing the Road Before You Feel Ready

Crossing the Road Before You Feel Ready

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This episode explores why waiting to feel ready keeps men stuck behind masks of competence and isolation, and why real change begins before everything feels safe or polished. Through stories of reconciliation, the Good Samaritan, and Jesus’ call to follow, the hosts make the case for crossing the road, moving toward others, and choosing courage over perfection.

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Chapter 1

Why Waiting to Feel Ready Keeps Men Trapped in Isolation

Graham Caldwell

You know, er, I was, I was looking at that truck out front earlier, Dave, and it, it reminded me of this old Ford we had up in Wyoming. Starter was completely shot, but every Monday morning, like clockwork, we would just tow it up the ridge, park it on an incline, and pop the clutch. Ran fine once it was moving. But if you let it sit at the bottom of the hill waiting for a fresh battery, well, you were walking.

Dave Sheets

That is, er, that is so many men I talk to, Graham. Honestly, we sit at the bottom of the hill waiting for the, the perfect conditions before we turn the key. In the book, I call it the first lie every man believes. This idea that, well, if people really knew what was going on underneath the hood, they would walk away. So we manage the image. We build this incredible wall of competence.

Graham Caldwell

Yeah, competence. You get real good at your job, or, er, or fixing things on the property.

Dave Sheets

Right. Or even religious busywork! You know, I spent thirty years in Christian publishing, editing manuscripts about faith and courage, speaking at conferences, handling big book rollouts. From the outside, I looked like a guy who had it completely figured out. But inside? Man, I was hiding behind performance. I was, I was terrified that if I stopped producing, if I dropped the mask for even a second, the whole house of cards would fall.

Graham Caldwell

It is a clever trap because, uh, because the mask is impressive to everybody watching. Nobody questions the guy who gets results.

Dave Sheets

No! They applaud him! But here is the tragedy. People might admire the mask, but nobody can actually love the man behind it, because nobody is allowed to see him. You wind up completely isolated in a room full of people praising you. And we keep holding out for this magic day when we feel clean enough or ready enough to finally open up.

Graham Caldwell

Mm. Which never comes.

Dave Sheets

Never! Because that is not how Jesus operated. That is why I refer to him as the Original Outlaw. He did not sit around waiting for people to polish up their lives before he walked into their world. Look at who he called! He walked right up to tax collectors sitting at their booths, fishermen covered in sweat and fish scales, guys with messy histories, and he did not say get your act together and then come find me. He said follow me. The transformation happened out on the road while they were moving.

Graham Caldwell

Reminds me of fixing fence lines out on the ranch in early spring. You got a break in the wire down by the creek, mud up to your knees, cattle starting to wander through into the brush. If you sit back at the barn waiting for perfect dry weather before you go out there with the stretchers and staples, man, half your herd is gone into the timber. You got to go into the mud while the hole is open.

Dave Sheets

That is it right there! Love moves first. It does not wait for a invitation, and it does not wait for safe weather. Safe distance is where we admire Jesus, but apprenticeship requires us to step out into the mud with him.

Graham Caldwell

So how does a guy actually break out of that spectator mode? Because sitting in the grandstands feels a whole lot safer than stepping onto the dirt.

Chapter 2

The Physical Act of Crossing the Road

Dave Sheets

It takes a physical act. You have to move. I remember a brother who came out to one of our gatherings around the fire at Outlaw Ranch up in the Spanish Peaks. He had been estranged from his son for nearly a year. Eight or nine months of dead silence after a massive blowup. Both of them sitting on their pride, waiting for the other guy to pick up the phone and apologize.

Graham Caldwell

The old standoff. Classic.

Dave Sheets

Total stalemate. And this dad is sitting by the fire explaining his position, and look, his position was reasonable! The son had said some awful things. But one of the guys in the circle looked across the sparks at him and asked, do you want to be right, or do you want your son back? And that night, that dad drove home, got up the next morning, walked across a two lane highway, and knocked on his son's front door.

Graham Caldwell

Wait, he just, he just showed up?

Dave Sheets

He just showed up. No long speech prepared, no scorecard in his hand to prove he was justified. Just knocked on the door, and when his son opened it, he said, I do not know how we fix all of this, but I love you, I miss you, and I am sorry for my part in the mess. That is crossing the road. That is moving from intention to action.

Graham Caldwell

Man. That takes real steel in the spine. Because you might get the door slammed in your face.

Dave Sheets

You might! Courage is not the absence of fear, Graham. Courage is faithfulness right there in the presence of fear. When Jesus told the story of the Good Samaritan, the religious guys had great excuses for staying on their side of the dirt road. Ceremonial purity, busy schedules, safety. Respectable reasons! But compassion only became real when the Samaritan let the wounded guy interrupt his travel plans and physically crossed over.

Graham Caldwell

That is where the rubber hits the gravel. It is easy to feel bad for somebody while you keep driving down the highway at sixty miles an hour.

Dave Sheets

Exactly. We trade actual brotherhood for private remorse or high sounding ideas. But around the fire, we throw out the scorecards. Healing does not start when you have all the answers. It starts the second you stop pretending and let another man see the actual version of your life.

Graham Caldwell

So for the guy listening right now, sitting in his truck or walking on the treadmill, what is the next step? What does crossing the road look like today?

Dave Sheets

Stop waiting to feel ready. Pick the one doorway or the one phone call you have been routing your whole life around to avoid. Name it. Maybe it is telling your wife the truth about a secret habit, maybe it is calling your brother, maybe it is asking another man for help because your business is drowning and you cannot carry it alone anymore. You do not need light for the whole ten miles ahead. You just need enough light for the very next step. Take the step.

Graham Caldwell

Take the step. That is it. Leave safe behind, get out in the dirt, and start following. Good talk, Dave.

Dave Sheets

Good talk, Graham.