The Journey to Becoming a Real CEO

Everyone loves the title “CEO.” But the reality is you don’t step into that role the day you form an LLC. Becoming a CEO is a progression, and each stage forces you to let go of control, reshape your responsibilities, and trust others to carry the weight of the business.

Step #1: Owner-Operator

This is where I started. I was a plumber on the tools, doing the work myself every day. The plumber fixes pipes, the baker makes bread, the CPA files returns—it’s all the same story. You’re both the technician and the owner, which means you’ve just traded one job for another.

Michael Gerber calls it the “entrepreneurial seizure” in E-Myth Revisited. You love the craft, so you start a business, but then you realize running a business has very little to do with the work itself. Ownership feels real, but the business is 100% dependent on your effort. That’s what pushes you into the next stage.

Step #2: Manager of Workers

Growth forced me to hire help. The daily tasks shifted to employees, and my role became managing the people who did the work. This is one of the hardest stages to leave.

I went through the same identity crisis that most owners face. Do I stay in the field because that’s what I’m good at, or do I move fully into management? The pitfall here isn’t money—it’s mindset. To move forward, I had to stop thinking like a technician and start acting like a leader. Until you make that shift, you’re stuck bouncing between both worlds.

Step #3: Manager of Managers

As my team grew, the business needed real infrastructure. I added office staff, call takers, bookkeepers, and frontline managers. These roles didn’t directly produce revenue, so the financial strain was real.

This stage is what I call “owner’s hell.” Rent, managers, software, and overhead all pile up, but the payoff doesn’t come quickly. In trades, this phase can last from $2–3 million in revenue all the way to $15 million. It’s a grind, but the grind is the point. You’re replicating functions, hiring more managers, and building the structure that makes scale possible.

Step #4: Leader of Leaders

Eventually, I wasn’t managing frontline staff or even their managers—I was leading senior leaders who oversaw entire functions like operations, finance, marketing, and HR. My job became aligning those leaders and setting the vision.

This was the first time I really felt like a CEO. At 150–160 employees, I had multiple layers of managers and directors reporting up through the org chart. I wasn’t close to the call center or the sale anymore, which slowed things down. But I realized that if something was too slow, it usually meant we didn’t have a process for it—not that my people were wrong. At this level, speed only comes from trust, process, and buy-in.

Looking Ahead: Stage #5

I’m not there yet, but the next stage is clear: multi-location and multi-state growth. That’s where reporting structures matter even more, and leadership depth becomes the only way forward. I like to compare it to steering a cruise ship instead of a speedboat. Everything takes longer to turn, but the impact is much bigger.

For me, the lesson has been simple: CEO isn’t a title you claim. It’s a role you grow into. Each stage demands that you step back further from the work, trust more of your team, and keep leveling up your leadership.

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