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I'd say when you're comfortable you have a general sense of fulfillment, and you're still learning and growing. When you're too comfortable is when problems arise. People can get complacent and their productivity suffers. And they stop learning or even wanting to. They wind up saying the worst thing possible: But that's the way we've always done it.
Chief
Getting too comfortable means being content is not advancing at all and spending the rest of your career at your current position.
Probably when you aren't learning anymore