I stayed at Amazon for 18 years. One company for my entire career, from new college grad to Principal Engineer.
Who am I to write about knowing when to leave?
For me, staying that long wasn’t a single decision. It was a decision I made over and over again, year after year. Not by actively choosing to stay, but by never seriously asking whether I should go. And that’s exactly the problem most people have.
We don’t decide to stay at our jobs. We just don’t leave. Staying is the default and the path of least resistance. Leaving requires significant action, risk, and disruption. Staying requires nothing at all.
So we wait until something forces the question, like a bad performance review, a toxic coworker and the headaches they create, or a layoff. We wait until the pain of staying exceeds the fear of leaving, but by then, we’ve often stayed years longer than we should have.
But why should a negative event be what triggers this decision? Why aren’t we asking the question proactively, when we s…
