re: Should I reach out to hiring manager who is also an acquaintance of my boss?

You should try being honest with yourself. You're acting like a gutless chicken. No spine. You want to get a supposed rare job opportunity so you go onto a message board and ask grown ups to hold your hand.

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I would tell your boss this is something you would like to pursue and ask if he would be willing to give a reference. This accomplishes two things:

1. If your boss is good and you are a good employee, it will remind him he needs to treat you correctly to keep you there
2. If your boss is willing to give you a good reference, you know he/she is pleased with your work.

If you boss is a good manager/director, he/she will understand and I only wish the people working for me the best in their careers. If I can help them achieve that, even if not working for me, then I always help good employees.

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Bad advice. Sure everything can be love and marriage if the conversation goes well (which I wouldn't hold my breath on), but if this job change is never realized you have really taken the pressure off your boss to bat for raises/promotions for you down the road. Why would he stick his neck out for you later on if you've openly disclosed a dream of moving on?