Ask a Hot Mess: How do I survive a difficult boss?

Scarlet Meyer
4 min readNov 22, 2017

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Note: Scarlet Meyer is a writer and comedian. All opinions expressed on this advice column are her own, and if they backfire on you it’s your own fucking fault Mike geez.

Happy Tuesday friends! I’m very excited to announce the official start of my advice column, ‘Ask a Hot Mess’! I was really excited to get some messages on Sarahah last week mostly because I was expecting none. This is the first one I received because I’m nothing if not fair and loyal to whatever nice person in my life decided to play along with my advice column pipe dream. This week’s message is from Sad Capitalist, who is, as you may have guessed, sad and a capitalist. Which makes sense because capitalism is flawed and a huge bummer! Anyway:

Hey,

My boss is a straight up dum dummy. What can I do to make my day less miserable when interacting with his b to the s?

With love,
Sad capitalist

Hey there Sad Capitalist,

Thank you for writing! I’m sorry to hear that your boss is a straight up dum dummy, that’s unfortunate. Although I don’t know much about the context of your situation I’m going to assume ‘dum dummy’ refers to someone who you are contractually obligated to listen to who makes decisions that you don’t think are well thought out. Not someone who is putting you in a dangerous situation (that’s what HR is for) or someone who annoys you but you can be zen about. I’ve been lucky enough to have had some wonderful bosses, but I’ve also worked for people who I might euphemistically refer to as ‘strong personalities’ if you were asking me in an interview. (You’re not, but still.) However the reality of work is you’re going to have to work with people you don’t get along with sometimes. Like really don’t get along with. Like if you were in an apocalypse scenario and they were the only person you were left alive with you might just say ‘no thanks’ and go chill with some nuclear wolves. It can be that bad. However we’re grown ass adults who need money so we don’t get evicted or starve, so sometimes we have to deal. Here is how I’ve learned to survive while working with other people’s b to the s:

  1. Befriend them. This might sound like the worst thing ever, but hear me out. The best way to diffuse a weird work relationship is to make that person your friend. Even if you think they hate you, just go with it. Do they have a cat? Ask questions about their cat sometimes. Do they have grandchildren? Same deal, and you better believe you’re going to look at those photos and talk about how cute and smart those kids are! Do they like a TV show? Guess what you’re going to sit down and watch an episode of later? The reality is that people are nicer to their friends. It’s easy to be a jerk to someone you don’t like, but it’s harder to do that to friend. You can find common ground with anyone, or at least pretend to. Be a friend.
  2. Remember: bosses are people too. A manager of mine once told me something that blew my mind: He believed there was no nice way to critique someone’s performance or tell someone what to do. That no matter which way you approach it someone will have a problem with it. I kind of think he was right. Even though I try really hard to be #chill I know I personally always get defensive when someone critiques my work. (Like this advice column for example)! Understand that your boss probably never was a little kid dreaming of becoming a middle manager someday while other kids were dressing up as firefighters or astronauts. True, maybe they’re not great at what they do, but they are presumably trying their best. If your boss tells you to do stuff that is annoying to you, try to look past how they’re saying it and understand the reason why they’re saying it. It’s technically their job to nag you, be nitpicky about your work, and in general play the bad cop. That just comes with the territory, and is nothing personal. (Although it can be pretty annoying depending on how they handle it. ) I know it’s hard, but try to cut them a little slack.
  3. Ok but my boss is really dumb and full of shit: I get it. I’ve been there too. Sometimes you really just can’t make peace with someone you’re working with. Sometimes their decision making is so poor or erratic that you can’t even understand how they walk down the street without tripping on their untied shoelaces. In these cases I would recommend limiting your time with them and picking your battles. Try to have as little face time as you can without compromising your work. I also cannot express the importance of a paper trail. If you see a work problem happening down the horizon, make sure you mention it over email so you can have a time and date of you warning them of imminent disaster. Be nice, but keep your receipts. If they’re going to pitch a fit or try to blame you for something that isn’t your fault make sure you have concrete backup to prove your innocence. And if it’s really so bad that their behavior is overwhelming and affecting your mental health? Start looking for work elsewhere. Unfortunately Sad Capitalist, we spend most of our time at work. If your boss really sucks that much, that means you’re spending the majority of your waking hours with someone you hate who is making you feel crazy. And who wants to do that?

I hope this helps! Again, sorry about your dum dummy boss. If you’re one of my many friends (I’m mad popular) ask me to hang out and we can vent about this in person.

Sincerely,

Scarlet Meyer, the hottest of messes

Got a messy question you want answered? Send it to Ask a Hot Mess and your question could be featured on this highly exclusive advice column that definitely has more than three submissions so far!

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