The Road to 50 - Week 4
Discomfort Is a Signal, Not a Stop Sign
There's a reason we instinctively move away from discomfort.
Our brains are built to protect us. When something feels difficult, uncertain, or threatening, the instinct is simple: Get out. And sometimes that's exactly right. However, in our modern world that is designed for comfort, it is rarely the case. But what if we could tell the difference between discomfort that's warning us and discomfort that's changing us? That question has been with me since the San Juan 50 Miler.
I read Michael Easter's description of Separation, Transition, and Incorporation in The Comfort Crisis, and I immediately thought: That was the starting line for me! A choice to leave the familiar. Enter the struggle, and embrace what the day would bring. What I didn’t realize during this process was simply by choosing struggle over comfort, I was growing in ways I could not recognize in the moment.
The more I sit with it, the more I realize that's exactly what fifty miles taught me.
Separation
First when you choose discomfort, you leave what's familiar.
You step away from comfort and into something that challenges your definition of "normal."
For me, that was the starting line at 5:00 a.m. Fifty miles ahead. Mountains. Altitude. And no real idea what the day would bring — injury, storms, route-finding, solitude, all of it is possible which creates loads of uncertainty. But here is what I knew at that moment; I did the work for this very moment. I'd trained for months, logged the miles, executed the strength sessions, and focused on intentional recovery.
But, training doesn't always remove uncertainty. At some point you stop preparing and actually enter the experience. That's separation. The separation from what we know and step into the unknown. And we do it in life all the time. A new role. A hard conversation. A career change. Feedback we don't want to hear. Any decision to pursue something that might expose our limits because we are intentionally leaving our comfort zone. And here’s the beauty of separation. By choosing to separate, we are opening ourselves up for growth.
Transition
This is the part nobody puts on the highlight reel. It’s messy and often uncomfortable. Let’s be honest, when have you ever seen someone struggle on any social media platform?
It's the middle — where the challenge gets real and your instincts start talking. This is hard. I don't know if I can do this. Maybe I wasn't ready. Maybe I didn’t train hard enough. That was Mile 23 for me. The physical discomfort was real, but the mental struggle was louder. And it forced me to recognize something: discomfort doesn't automatically mean something is wrong.
Muscle fatigue isn't necessarily an injury.
Fear isn't necessarily danger.
Conflict isn't necessarily failure.
Feedback isn't necessarily an attack.
Difficulty isn't necessarily a reason to quit.
Sometimes discomfort just means something is being worked through.
The skill is learning to tell which is which. Here's the part I think we get wrong, though:
The goal isn't to get comfortable with discomfort.
The goal is to become more capable because of it.
That's what the Transition is for. You adapt. You develop skills you didn't have at the starting line. You find out you can sit with uncertainty without immediately reacting to it. You can stay in the struggle and still take the next step. And somewhere in there, something changes. A deep change that would have never happened by choosing comfort over struggle.
Incorporation
You come back different.
Not because the mountain changed. Because you did. This is the stage most of us skip. We survive the hard thing, we feel the relief, and we default back to our comfort zone — as if simply getting through it was the point. But surviving the challenge isn't the same as being changed by it. The real value was never in finishing the race. It's in what you carry back down the mountain when the day is done.
That's what I've tried to do since June 20. I don't want those lessons to stay on the trail. I want them in how I lead, how I show up in my marriage, how I respond to pressure, how I receive feedback, how I handle uncertainty — and how I help other people through their own hard challenges. Because if I go through something that hard and come back exactly the same person, what was the point?
Why this matters for leadership
Think about a leader who needs to have a difficult conversation.
Separation: They stop avoiding it and decide it has to happen.
Transition: It gets uncomfortable. Emotions rise. Every instinct says, make this go away. But you have the conversation anyway. You work through it, you feel the struggle, and realize that this is a signal of growth!
Incorporation: They come out of it with more courage, more empathy, more skill, and in the long run likely better relationships.
The next hard conversation isn't necessarily easier. They're just better equipped for it. That's growth. And it's why I don't believe leadership development is about making leaders more comfortable. It's about making them more capable.
The San Juan 50 reminded me of something I don't want to forget: Discomfort is often just the feeling of growth happening in real time. But you have to stay long enough to learn from it. Not all of it, though. Some discomfort is a warning. Some is a boundary. Some are signals to change direction. And some is simply the feeling of becoming someone you haven't been yet.
The work is learning the difference.
Take the Next Step
Think about something uncomfortable you're facing right now. A conversation. A decision. Feedback. A new responsibility.
Ask yourself: Am I trying to eliminate this discomfort — or learn what it's trying to teach me?
Maybe the question isn't "How do I get out of this?"
Maybe it's "Who might I become if I work through it?"
Discomfort is a signal, not a stop sign.
Learn to listen. Learn to discern. Then decide whether the next step is to stop — or to keep climbing and see what you are capable of.