It’s annoying, but knowledge is power - figure out how to use this knowledge to your benefit

I had a boss who would brag about how he didnt know how to spend his overfunded college plans when his two kids got full ride scholarships to ivy league schools already and how he figured out that it can be passed to grandkids who were not even born yet. He said it wasnt that hard, just made his kids do varsity tennis and golf. Then proceeds to tell everyone why the heck we werent doing the same thing... BUT he made me payback $60 for using an extra maternity pump set when I forgot mine ("We just allow one per employee per maternity leave") and announced this in front of a freaking staff meeting. I left as soon as I had another offer in hand.

I had a former Fed supervisor like this - she was so terrible that management finally reassigned her to a non-sup position and she’s been in an irrelevant corner since, swearing she’ll die at her desk. I’ve never met anyone quite like her before or since. Obnoxious, exaggerated NY accent, bragged incessantly about her multiple “unencumbered” properties on Long Island (and she’d always giddily crow, “Do you know what unencumbered means? No mortgage!”), and just complete lack of self-awareness or tact.

She would also brag almost daily about how much was in her TSP, how she had been spoiled rotten growing up as an only child from her successful business owner father… and on and on and on. Yes, she’s a boomer.

I was early in my career, but finally realized I didn’t need to be held hostage by her and tuned her out. Made for some good entertainment, but was annoying when work actually needed to be done.

I had one boss go on and on about his inherited wealth and how I wouldn't understand.

Also it’s annoying that, we’re spending so much time talking about his latest vacation but I can’t get his true attention on work that is important for our team. He’s just self involved.

My boss is so like this. I hear more about his vacations, his adult children, his vacation home renovation, his illnesses than I care about. Meanwhile he can’t even remember my husband’s correct name or ever ask about me in a meaningful way.

I chalk it up to 1) him being a pretty traditional boomer white man and being a poor listener, and 2) he’s not my friend, there’s a different power dynamic there.

Don’t caste pearls before swine and expect most coworkers to give a $hit about your life.