Life Advice



Ask Amy: Nightmare bosses bust through boundaries

Amy Dickinson, Tribune Content Agency on

Dear Readers: Every year during this time I step away from my column to work on other creative projects. I hope you enjoy these “Best Of” Q&A from 10 years ago, which I’ve retrieved from my advice-vault.

Today’s topic is: “Whoa – That’s Inappropriate!”

I also invite readers to subscribe to my weekly “Asking Amy” newsletter, at, where I post advice, as well as commentary about what I’m reading, watching, and listening to.

I’ll be back with fresh Q&A next week.

Dear Amy: I am about to take a job at a prestigious professional services firm.

My boss makes everyone stay at his house in a city out of state for regional group meetings a few times a year.


We have to stay in his house, in his daughter's room, in the spare rooms, etc.

I think this is wrong, and it is not something I want to do. However, now I feel like I have to do this, because everyone else has been doing it for years.

I could get a hotel, but it will make me seem like I am not part of the team.

I worry about privacy, about feeling awkward, and about my tendency not to be myself when I stay at other people's houses. What should I do?


swipe to next page



Curtis 1 and Done Agnes Monte Wolverton Joey Weatherford Dilbert