i want to hear about your best and worst bosses
let's have a conversation about the good, the bad, and the ugly!
It’s Monday, but this isn’t a Short Stack. Instead, dear readers, I’m coming to you today with a request. (There’s a picture of two at the bottom for those of you who just want to see what Bessie is doing, though.)
I’ve been thinking a lot lately about bosses, mostly because I don’t have them anymore. As a freelancer, the only people I have to answer to now are my clients. Client relationship management has always been one of my strengths, so this is ideal for me (even if socialization and phone calls and showing up to businesses in person can sometimes be very challenging for my introverted self). I have had decent luck with easygoing clients over the years, and especially now that I have some say in who I work with.
Bosses? Not so much. Like, I’ve pretty famously had some of the most inappropriate, condescending, selfish bosses a person could dream (nightmare?) up. Supervisors at multiple agencies who violated ADA protections, female directors known for keeping their female subordinates from advancing, and team leads who didn’t believe what I was telling them about my direct reports until I went on vacation for two weeks and they had to find out for themselves. 🙃🚩
It’s true what they say: people don’t leave bad jobs. They leave bad bosses.
When I think back to all these atrocious experiences I’ve had with supervisors or listen to my friends tell me horror stories about their current bosses, I am even more appreciative for the very few truly great leaders I’ve worked with. I can count on one hand the bosses who gave an actual shit about my personal wellbeing, professional development, and growth as a manager myself, but my God did it make a huge difference just to have those few.
So what about you all?
Do people generally have more positive or negative experiences with their supervisors? How does what we look for in a good boss change as our careers advance? Is what makes a good or bad boss different depending on the field you work in? Did you have a perfect boss who had just one horrible habit you could never get over?
If you have a minute this week, use this form to tell me about what makes a good or a bad boss to you. Otherwise this is going to be very embarrassing for me if nobody responds. And besides, aren’t you just a little bit nosy about other people’s experiences, too? 😉
Stay tuned for the follow up!


I love her and her ice cream obsession- also need to get back to this this week to share some stories haha