“Discipline equals freedom. Push through the discomfort, and growth becomes your reward.”
– Jocko Willink
At this year’s Harvest of Knowledge conference, this lesson hit harder than any motivational quote: your level of success is directly tied to your ability to endure and process pain.
Not just physical pain.
Not just the grind.
But the deep, gnawing, leadership pain that shapes every decision, every relationship, and every outcome.
Early in our leadership journeys, the pain is raw and personal. You’re learning the hard way that not everyone is going to show up the way you hoped. Employees will disappoint. Mistakes will happen. You’ll make decisions that keep you up at night, second‑guessing whether you did the right thing. There’s the pain of terminating a team member you personally like but who isn’t performing, the frustration of cash flow tightness when the bills start to pile up, and the weight of tough clients who don’t appreciate the value you deliver.
That early pain is a defining moment, because it teaches you what level of discomfort you’re willing to tolerate. And here’s the trap most leaders fall into: once the early pain subsides, we subconsciously settle into the level of pain we’re comfortable with. We create a ceiling for ourselves. A safe zone. And unknowingly limit our growth.
But growth doesn’t happen in comfort zones. As you move up the ladder, the pain evolves. Middle leaders deal with operational breakdowns, the stress of aligning multiple departments, and the pressure of being both the problem solver and the visionary. Senior enterprise level leaders? They live in a world where the stakes are massive. The pain of missing revenue targets can mean millions of dollars, the weight of letting go of long-tenured senior managers or directors is emotionally devastating, and every decision reverberates across hundreds or maybe thousands of employees, and clients. At this level, the pain isn’t just personal – it’s systemic. The entire organization feels it when you make the tough call.
Craig Groeschel says “Life is full of setbacks, but God uses every setback to shape your leadership.”
Here’s what I learned watching some of the top leaders in our industry share their journeys: pain is inevitable – but endurance is optional. The most successful leaders don’t avoid it; they embrace it. They lean into the discomfort, knowing that growth, influence, and lasting impact live on the other side. And when you push past your “comfortable level of pain,” you discover a capacity for leadership and resilience you didn’t know you had.
Pain teaches clarity. Pain teaches humility. Pain teaches strategy. It teaches you which battles are worth fighting, which people can carry the weight with you, and which ones cannot. It’s the difference between a leader who survives by luck and one who thrives by design.
The truth is, the level of success you experience in your business, in your career, and ultimately in your life is measured by how much pain you can process without letting it crush you. Every tough conversation, every sleepless night, every difficult client meeting – these are all training. Each painful moment is a rep for your resilience muscles.
Here’s the challenge: embrace it. Don’t retreat to the comfort of the pain you’re used to. Lean into what feels uncomfortable. Learn from it, let it sharpen you, and watch as your capacity to lead – and your impact – expands exponentially.
Because at the end of the day, leaders aren’t defined by the absence of pain… they’re defined by how they walk through it.