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Agreed. It's not hard to tell how someone is feeling about their position. Your boss probably wants to find something for you that you'll be happy with as much as you do, the pain of losing someone good sucks, but it's worse watching them toil away unhappily for you.

This. I've only had to do this a few times in my life, but it always seemed worse than it was. Just be straightforward and honest, it'll all turn out just fine.

Totally agree. Worrying about it ahead of time always ends up being worse than actually doing it.

Thanks, the both of you.

> Ask your boss for a private meeting.

I once emailed my boss to say that I want to talk to him about some career choices I've made. When we finally spoke, he was mentally prepared for my resignation.