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I left a company to go back to school (took on massive loans). A few months later, the company closed up and people got extremely generous severances. Would have probably covered half my tuition costs. I definitely wish I had stuck around THAT company longer!

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Which illustrates the original point: that scenario -- generous severances when the company is going out of business -- is incredibly rare. A much more likely scenario is your options become worthless and you're laid off. If you can leave a bad environment, I recommend leaving ASAP instead of letting the golden handcuffs keep you -- unless the golden handcuffs promise a huge return, and there's little or no doubt about getting that return.

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