Sometimes leaving is the right outcome.
I’ve watched it happen.
Think about the employee everybody loves. Friendly. Nobody wants to lose them. They miss deadlines and quietly hand their work to the people around them. Everyone knows it. Nobody says it. Then they give notice, and the first thing the owner says is, “We can’t afford to lose them.”
You will feel the gap. But ask what that person was costing you while they were here.
Someone good leaves for a bigger company that can offer a path you can’t. That one stings. It’s also the business working. You trained someone who got better, and someone else saw it too.
I did 20 years in the Navy. The longest I was ever at one command was four and a half years. On a crew of 150, about ten of us were there when I showed up. People rotated out every few years. The mission still got done, because the work was written down and the people coming in knew how to run it. Turnover was built into the system. Nobody treated each departure as a crisis.
A bookkeeper I hired learned bookkeeping, payroll, and sales tax with me for about three years. Then he got a job at a university that came with a free master’s degree. I told him to take it. We left on good terms, and I was glad I’d helped him move on.
Most owners can’t do that, because they never decided who they want to keep. Every resignation feels like a loss, so they fight to hold on to everyone at the same level, including the people they’d be glad to see go. Retention turns into a reaction. The owner reacts to whoever threatens to quit, and the good people who never complain get taken for granted.
Start by deciding who you’d fight to keep. Then decide who you’d be glad to see go.