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The Question:
Personal Development: How do you know it is time to look for a different job?

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When you don't have passion for what you are doing anymore!

When somebody you know and trust makes you an offer you can't refuse, and not before. That said, always be working towards being the person that will be made that offer. Priority number 1, even if you are a CEO, is to know who your boss will be. If that isn't going to be bettered, with a high degree of certainty, then don't jump. Never run away from things, always be called forwards. Unless the thing is a lion of course!