re: Job A/Job B Advice

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Sounds like you're in a good position though!

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I am. Best career spot in my life. Company A is obviously a university, so its pretty safe. The tuition benefit has been around for a long time, I don't see it going away because faculty members are recruited with the promise that their children can go to an expensive private university for free.

Company B is a private entity that deals with education. Its an intriguing opportunity. One option that a friend brought up to me is actually offering to do some consulting instead of taking full time employment. That would probably make up the 20% gap.