When I Knew I Was Done Working for Other People

Built From the Field by Chris Momongan

🗓️ Posted: May 1, 2025

✍️ Category: Origin Stories / Career Pivots

It started with a conversation with my wife.

She had just had a rough work interaction—and as she vented, I could feel it in my chest. Not just because I wanted to support her, but because it mirrored every toxic work situation I’d ever been through.

I’ve had bosses who were insecure, incompetent, or chasing goals that directly clashed with mine. And the worst part? It always felt like we were in competition instead of on the same team. Like we were both hunting the same animal—trying to outpace each other—instead of hunting together to feed the same village.

A good manager should build you up, not feel threatened by your growth. They should advocate for your development, not play small politics to protect their ego.

At my last job, I had one of the best managers I’ve ever worked with. She supported us. She led with clarity. She had our backs. But when she moved on, her replacement was the opposite.

I brought up something that had made me deeply uncomfortable in the workplace. Her response? Silence. No follow-up. No acknowledgment. It was like I’d become invisible overnight.

That was the moment.

The moment I knew: I’m done working for other people.

🌊 A Line in the Sand

Not long after, I told Myredith I needed a reset. We took a spontaneous trip to the beach. On that shoreline, I said the thing out loud:

“What if I quit and just went all in on investing?”

We’d talked about selling our house before, but this time I meant it. We had equity. We had a shot. We just didn’t have a clear roadmap.

We couldn’t rent it out due to restrictions. We didn’t want to live there anymore. That’s when Augusta came to mind. My parents had a big house—we figured maybe we could use it as a launchpad while we figured things out.

I thought it would be simple. It wasn’t.

But what mattered was that I was finally moving away from what I didn’t want and toward the unknown. And that clarity was all I needed to get started.

🔁 Takeaway

Sometimes the moment you hit your limit is the moment you pivot toward your future.

There’s power in that breaking point—if you’re willing to move.

🔗 Follow the Journey

More stories like this — real, honest, and from the field — are coming soon.

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