How Losing My Top Employee Nearly Killed My Business

And the 3 Lessons That Saved Us

Oct 06, 2024

A couple of weekends ago, I was having the absolute worst time. Chronic pain had me doped up on muscle relaxers, and my wife and I were at odds — (completely my fault). Just when I thought the weekend couldn’t spiral any further, I got a message from one of my top employees. Due to life problems they were dealing with, they couldn’t continue working with our company.

Now, this setback hit hard. Not just because losing any employee sucks, but this particular one was our biggest content contributor. For a newsletter-driven business like ours, losing such a key contributor is a crisis. I genuinely thought we’d have to shut our project down.

The rest of the weekend, I was in a daze, wrestling with how to break the news to the rest of the team. I researched everything I could on how to address a group after a loss. How do you express disappointment without killing their morale? How do you tell them the vision we’ve been building might be done for?

By Monday morning, I felt like a failure. Sure, it wasn’t technically my fault the employee left — no one’s fault, really — but I still felt like I’d let everyone down. I had gathered this team, made them believe in the mission, and now I was ready to tell them it was over.

Then came the content meeting.

I logged in, trying to keep it together. And what I saw surprised me: my number two was ready to roll, sleeves up, prepared to figure out a way forward. My editor soon followed, just as ready to dig in. Neither of them knew about the bomb I was about to drop, yet their energy made me rethink everything.

In that moment, it hit me: we weren’t dead in the water. This disappointment wasn’t the end. We could pivot, adapt, and keep going. We didn’t need to shut down; we needed to lean into the challenge. That realization gave me clarity and taught me three key lessons.

1. Don’t Bottleneck Your Business

It’s easy to lean on one person — or yourself — when resources are tight, but that creates a fragile system. If that person goes, you’re stuck. The solution? Train your team to be utility players. Everyone should know enough to wear multiple hats. For solopreneurs, consider outsourcing — hiring a VA, or using platforms like Upwork or Fiverr to keep things running when you can’t. Your business should never rely on just one person.

2. Hire Problem Solvers Over Specialists

At that content meeting, I realized my team wasn’t just filled with specialists — they were problem solvers. Faced with a major setback, they didn’t panic; they got creative and found solutions. If I’d focused only on hiring specialists, we might’ve been stuck. When hiring, prioritize problem-solving skills over experience or specific expertise. You’ll face more situations that require quick thinking than niche knowledge.

3. Trust Your Team

My biggest mistake? Not trusting my people from the start. I treated the loss as a “me” problem, when the situation was an OBA Studios problem. Once I brought the team into the issue, they rose to the challenge and came up with ideas I hadn’t even considered. If you’ve hired a team, trust them. They’re there for a reason, and their input can lead to results that surpass your expectations.

Losing a team member is never easy, and it’s hard not to take the setback personally. But every loss is a lesson, a chance to find something valuable in the mess. For us at OBA, it was an opportunity to see just how capable we are. Losing someone isn’t the end — it’s a test of resilience, and we passed.