Horse and rider
Photo: Studia72
"Taking on a challenge is a lot like riding a horse, isn’t it? If you’re comfortable while you’re doing it, you’re probably doing it wrong.” —Ted Lasso
This simple metaphor captures a universal truth about growth: real progress happens at the edge of your comfort zone. When you’re balanced, relaxed, and cozy, you’re probably not stretching yourself enough. Whether you lead a family, congregation or organization, it’s essential to navigate moments of unease, because that’s where innovation, resilience, and transformation live.
Edwin Friedman understood this paradox better than most. In his work on family systems and leadership, he argued that effective leaders don’t just need to embrace discomfort—they need to learn to love it. Why?
Because discomfort is the only reliable indicator that you’re pushing against the edges of what’s possible.
Side note: Our brains are wired to avoid uncertainty and seek predictable patterns. This kept our ancestors alive, but it also keeps us playing it safe when breakthrough requires risk.
Think about the last time you made a decision that felt genuinely challenging. I’m not talking about choosing between two good options, I mean the kind of choice where you weren’t sure if you were being wise or foolish. Where you had to act on principle without knowing the outcome.
That knot in your stomach? That’s not a bug in the system. That’s a feature.
Or, as Seth Godin wrote:
“This might not work. At some level, ‘this might not work’ is at the heart of all important projects, of everything new and worth doing. And it can paralyze us into inaction, into watering down our art and into failing to ship.”
If you want to make a difference in the world, moving forward when you are saying to yourself, “This might not work” is a must.
Friedman called this having a bias toward challenge rather than comfort. Growth, whether personal or systemic, only occurs when we’re outside of our comfort zone. Most people and relationship systems gravitate toward comfort, safety and predictability. A bias toward challenge is the OPPOSITE of prioritizing comfort over the possibility for growth.
Here’s what I’ve learned about discomfort: it’s the only reliable compass pointing toward growth. When a conversation feels too easy, I’m probably avoiding something important. When a decision feels obvious, I might be choosing the familiar over the necessary.
But here’s the twist—and this is where Friedman’s insight becomes revolutionary: you can actually learn to love this feeling. Not because you’re a masochist, but because you begin to recognize discomfort as the leading edge of transformation.
Why do I share this? Because most of us spend enormous energy trying to avoid the very experiences that could make us better leaders. We choose comfort over growth, predictability over possibility, consensus over conviction.
Friedman understood that anxious systems—whether families, churches, or organizations—will always pressure leaders to choose the comfortable path. They’ll reward you for keeping everyone happy and punish you for creating productive tension.
The non-anxious leader learns to recognize this pressure and leans into the discomfort anyway.
Pay attention to the moments when your leadership feels too comfortable. Notice when you’re making decisions to avoid anxiety rather than to create positive change.
Then remember Ted Lasso’s wisdom: if you’re completely comfortable, you’re probably doing it wrong.
The question isn’t whether leadership will be uncomfortable. The question is whether you’ll learn to love the discomfort that comes with making a difference.
Recommendations
This week's posts will help you learn to love discomfort.
[Outliers] Rose Blumkin: Nebraska Furniture Mart from The Knowledge Project Podcast. Talk about someone who embraced discomfort. I'd never heard of Rose Blumkin before, but I'm a big fan of The Knowledge Project, as it focuses on what it takes to make a difference. You don't need to listen to the episode, as the link highlights 10 lessons from her life. This is a must read if you want to make a difference.
A System for Strategic Sacrifices [3-Step Method] - Ben Meer The subtitle for this post is "The uncomfortable truth about achieving excellence that nobody talks about." Meer's three-step method is simple but not easy. Don't skip this one if you want to make an impact in the world.