Always ask yourself before you send an email, what are you hoping to do with the email? Get something out of someone? Maintain or build a relationship? Make

Always ask yourself before you send an email, what are you hoping to do with the email? Get something out of someone? Maintain or build a relationship? Make that person feel bad? Gloat? In this case it sounds like you had no purpose at all... Just "being nice". It was probably interpreted as "you are trying to make me feel bad" by your ex-boss. Note I did not say MISINTERPRETED, because that implies it is his fault. It is not, it is up to you to control how you appear and everything surrounding that messaging. You learned a hard lesson here, you lost a potential future ally. Shrug, learn the lesson and move on. And finally, it ie never improper to offer ex-coworkers jobs, just be aware of: - legal obligations wrt non-compete, and IP. it might be wise to honor an non-compete even if it isnt legally enforceable. Don't like non-competes? dont sign them. - relationship status and feeling. how will the other side feel?