Leadership regression has no warning light, no email sent to let us know, no moment where you wake up and decide you’re going to be a worse leader today. It happens quietly and gradually, one small compromise at a time, often while we’re telling ourselves we’re doing the right thing.
Most of us start our leadership journey with pretty good intentions. We care deeply about people. We want to build something meaningful. We have standards, values, and a clear picture of the kind of leader we want to be. Then pressure shows up. Growth pressure. Financial pressure. People pressure. If we’re not careful, those good intentions slowly give way to desperation, and desperation has a way of disguising itself as practicality.
That’s where regression begins.
“Discipline equals freedom.” – Jocko Willink
For me, that season was 2017 / 2018. Those were some of the darkest and hardest years of my leadership journey. The business was growing, but the foundation wasn’t strong yet.
We needed production.
We needed stability.
We needed systems.
We needed key people to show up and perform.
One Friday night, I got a call that still sticks with me. A foreman… someone in a role we couldn’t operate without at the time, called to tell me he had another offer. Better pay. And he was going to take it.
What happened that Friday night still makes me uncomfortable to admit. Against everything I believed about leadership, culture, and long-term health, I negotiated. I gave him a raise to get him to stay. In that moment, I wasn’t leading. I was reacting. I told myself I was protecting the business, but what I was actually doing was teaching a lesson I’d later pay for.
That night, after the call ended, I said something out loud that became a turning point for me: “I will never be held hostage in my own company again.” The reality is, that moment wasn’t the start of my leadership decline. It was the moment I finally realized how far I had already regressed.
“Everything rises and falls on leadership.” – John Maxwell
The level of your leadership can often be found in the level of problems you’re able to solve. Early on, leaders spend most of their time solving people problems. As they grow, they begin solving process problems, then systems problems, then culture problems. At the highest level, leaders are thinking about legacy. The dangerous part is that once you’ve climbed those levels, you don’t simply fall back overnight. Regression is subtle. It happens when you stop intentionally growing.
Once you’ve experienced strong leadership, mediocrity doesn’t feel out loud anymore. It feels familiar. Things that once felt unacceptable slowly become tolerated. Decisions that once required conviction begin to get negotiated away. Not because you don’t know better, but because pressure convinces you that survival matters more than standards.
Early in business, everything feels significant. A good employee. A big client. A key lead role. You protect those things at all costs because they feel rare. But once you’ve built systems, developed people, and created depth, you realize something powerful. What once felt rare becomes repeatable. Leaders who fail to grow don’t lose significance overnight. They cling to it.
“You don’t drift into excellence. You drift into mediocrity.” – Ed Mylett
Here’s the part no one talks about enough. Leadership regression is passive, but leadership growth is intentional. Once you’ve gotten somewhere, if you don’t work daily to become better, you will regress without even realizing it. Leadership isn’t something you achieve and check off a list. It’s something you maintain through discipline, self-awareness, and hard decisions.
I’ll land the plane with this… Nobody gets up in the morning and says, “I’m going to be a crappy leader today.” But plenty of leaders wake up tired, overwhelmed, and afraid to make hard calls. Slowly, they begin trading long-term health for short-term relief. And that trade always costs more than it seems.
If you were to study the graph I placed for the header of this blog, where would you place yourself?
Here’s the question I’ll leave you with. Where have you started negotiating with problems you should be solving? Where are you holding onto people, processes, or patterns because losing them feels scarier than rebuilding them? Leadership regression doesn’t happen overnight. But NEITHER does leadership growth. Both are built, or abandoned – one decision at a time!