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My Boss, the Chaos Creator
Unstuck Monthly | September 2025
Why aren’t the good people running things?
When Leadership Makes You Sick
I was having heartburn again. The third time that week.
At first, I blamed my diet. Then my schedule. Then stress from the usual workplace pressures. But as I sat in yet another Monday morning meeting watching the CEO announce another sudden pivot—the fourth in two months—I realized the heartburn wasn’t about what I was eating.
It was about who I was working for.
This was mid-career for me, and I was a senior leader at a growing company. My boss reported directly to the CEO, which meant I had a front-row seat to how decisions got made. Or more accurately, how chaos got created.
Our CEO moved at lightning speed. New initiatives were launched before the previous ones were evaluated. Money was committed without warning or explanation. People were hired and fired based on his latest conversation or mood. He had a talent for making himself the center of every decision while keeping everyone else guessing about what would change next.
The most exhausting part? He deliberately set individuals and departments in competition for his attention and resources, only to act surprised when collaboration broke down.
The Invisible Toll
Looking back, the physical symptoms were just the beginning. I was gaining weight, sleeping poorly, and dreading Monday mornings in ways I’d never experienced before. But the deeper impact was what the CEO’s leadership style was doing to everyone around me.
Good people were leaving. Others were burning out or becoming cynical. The talented, well-intentioned leaders I worked with were constantly scrambling to clean up the confusion and maintain some semblance of stability for their teams.
I kept thinking: these are smart, capable people who genuinely care about doing good work. Why aren’t they the ones running things?
That question became the start of my mission.
The Clarity That Emerged
Working for a chaos creator taught me three things that now anchor how I think about leadership:
Systems need clarity. When leaders constantly change direction or keep their decision-making process opaque, it creates anxiety throughout the organization. People can’t do their best work when they’re always having to guess what matters this week.
People thrive on autonomy, mastery, and purpose. But our CEO needed to be at the center of everything, denying people the autonomy to excel in their roles. His rapid-fire changes prevented anyone from developing mastery. And the inconsistent messaging made it impossible to stay connected to any larger purpose, or even to each other.
Carrots work better than sticks. The chaos creator’s approach was essentially management by crisis. This stems from a belief that if you keep people a little scared and a little uncertain, then they’ll work harder to prove themselves. The logic was flawed. What actually happened was that people became defensive, territorial, and focused more on survival than innovation.
The Mission That Formed
I never had a dramatic confrontation or final straw moment with the CEO. I found a natural breaking point in our annual cycle to leave, move to a new city, and try something new. In breaking from a chaos creator boss, I felt that change was needed for me and for the system-at-large.
That experience crystallized something important for me: there are too many well-intentioned, capable people watching dysfunctional leaders make decisions that hurt organizations and damage careers. We need more of those good people in positions where they can create positive change.
Breaking the Chaos Cycle
This is why I’m drawn to working with leaders who’ve experienced dysfunction firsthand. They understand what it feels like to work in chaos. They’ve seen the damage that bad leadership creates. Most importantly, they’re motivated to ensure it doesn’t have to be that way for others.
These leaders are the ones who say things like “I never want my team to feel the uncertainty I felt” or “I want to create the clarity that I wished I’d had.” They’re not trying to be perfect leaders—they're trying to be intentional ones.
Chaos creators exist. They are currently in important positions across our workplaces. But it doesn’t have to be this way. And you might be exactly the person to prove it.
Thank you for sticking with me!
Until next time,
Alex
P.S. If you’ve experienced leadership that made you sick or otherwise negatively impacted your career, I’d love to hear how it shaped your approach to leading others. Reply and share your story. Or forward this to someone who might need to hear that their difficult experience has prepared them for something important.
Self-reflection questions:
What leadership experience made you think “there has to be a better way”?
What specific practices do you now avoid because of what you experienced?
How has your difficult experience made you more intentional about creating psychological safety for others?
What kind of leader are you determined to become because of what you've witnessed?
Ready to create your professional future on your own terms?
I work with ambitious leaders who want to transform their difficult experiences into exceptional leadership capabilities. If you’d like to explore how your origin story could become the foundation for positive change, book a call to explore working together.
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