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Work Retire Mailbag Vol. 5: Negative Coworkers, Know-it-Alls and Living with Your Parents

Every month or so, we’ll be answering your questions about work, life and balance. Thank you to all who submitted questions, and for everyone else, be sure to email to have yours answered in the next version.  And don’t forget to subscribe to the weekly newsletter, where answers will be posted first. Check out last month’s mailbag here.

What are your thoughts on dealing with super anal/know-it-all coworkers?

These people are the most annoying but luckily can be easily manipulated into doing all of your work for you. They care about this job and want everything done a certain way, and you need to be weaponizing that. If someone’s giving you way too much feedback and keeps asking you to “change font size on slide 11,” you have the perfect opportunity to set them up in a Catch-22. Here’s how you do it.

1. Play along for a little bit. Make some of their changes, but not all them. This will piss them off and is honestly an absolute blast.

2. When they keep pushing back, remind them how time-sensitive this task is. Ask if they’d “prefer to execute the changes themselves” since they clearly have a “very specific vision for the deliverable that’s not being communicated effectively.”

3.There are three scenarios for what happens next

  • They agree to do the work. Congrats! You just got rid of some work and your coworker can go off and be OCD in peace.
  • They realize they’re being a little hands-on and accept your version. Congrats! You don’t have to do anymore work and you stood up to an asshole.
  • They continue to push back on you and insist you accommodate their changes.

In the instance of the last scenario, you can either do the work (lame) or go deep in your bag for my final tip.

4. Send them a link to a job opening in your department. Ask if they’d like to apply to work on your team since they clearly think they can do your job better than you. Pray they don’t actually take you up on it and end up becoming your boss and make your life a living hell.

“What if you moved this here?” “What if I just sent you the file and YOU moved that there, Jim?”

When do I stop worrying about getting fired at any moment?

Never. And it’s not because of imposter syndrome. It’s because all of your worst fears are actually true. You are horrible at your job and do not deserve to be in your position. Your boss hates you and has never met anyone less incompetent. Your coworkers think you’re a loser and have separate Slack channels making fun of everything you do. Even your significant other and roommates have lost respect for you after listening to you flounder during conference calls. I’m surprised you haven’t been fired already and you should honestly quit. Savor these last few days of employment and financial security because it will not last.

If I ask my dad for money, can I log that call into salesforce?

Absolutely. Plus, the more money you have, the more of your products you can purchase under a fake name to boost your sales scores artificially. It might seem counterintuitive, but you have to spend money to make money in this world. Any good salesman has a series of fake or stolen identities ready to go, in case they need to make a last second order for exactly $2,123 of product to hit quota. Worth it.   

On a separate note, this reminds me of my first office job, which was working at the alumni call center as a freshman in college. You’d basically spend 3 hours calling alumni, forcing small talk and then asking for money. People were SO MEAN about getting asked for money and I couldn’t handle it. We had one of those call center machines that automatically calls people, so I would just sit there for my shift, stare at the wall, and if anyone actually picked up, I would hang up immediately.

I was kindly not asked back the next year, but that’s ok! I was able to begin a lifelong pattern of internalizing negative interactions with strangers and avoiding my feelings by shutting down and pretending my anxieties don’t exist. It’s very healthy and comes in handy when you are an Internet comedian battling online trolls in your DMs on a daily basis.

How to Pray When Someone You Love is Stuck in Sin
Me before my call center shift begging God that no one picks up the phone and screams at me today.

How do you handle a co-worker who is EXTREMELY depressing at all times?

It shouldn’t surprise you guys that I have a ton of experience being the depressing coworker in the office. I run a blog called Work Retire Die and post daily memes about how much I fucking hate working. Can you blame me though? Work sucks and honestly, complaining is a lot of fun and truly addicting. If you’re trapped in a deep cycle of work toxicity, venting and shit-talking with your coworkers can feel like the only sense of control you have. Eventually, though you start to actively seek out issues and no matter what your company does, it’s wrong and offensive.

They give you free food and beer? Wowwww, of course they think they can bribe us with pizza and craft IPAs. They give you the day off to volunteer at a charity? Classic PR move that HR forced them into, plus now I’m even more behind on emails for tomorrow. They ask you to do the basic tasks of your job description? This place is a Serbian forced labor camp and I am organizing a violent rebellion.

Anyways, to answer your question, Mr. Question-Asker. I totally get that it’s frustrating to be around the negative coworker who complains constantly and I admire that you’re trying to remain positive. You spend like 70% of your day at work or thinking about work – you are allowed to want to be happy during that time period.  

Here are some quick tips when your coworker won’t shut the fuck up about how unfair it is that they’re paid to sit in a temperature-controlled room and type away on their little computer.

1. Smile and Nod

They probably have some legitimate gripes and hopefully, they’re at least funny about their complaints. Everyone needs to vent sometimes, so let them get it off their chest and sometimes they’ll actually stop. Most importantly, don’t try to argue with them about everything. They’re probably too far gone for you to actually convince them they’re wrong about their attitude, so don’t bother.

2. Disassociate

One of the best parts of adult life is when you realize you don’t actually have to put up with stuff that makes you unhappy. If this guy bums you out, go eat lunch with someone else. Don’t respond to his Slacks or comments. Put in noise cancelling headphones the second he enters a room. Stare at him slackjawed whenever he speaks to you and then turn around and walk away without saying a word. Fun stuff like that.

3. Be Above It

Keep in mind that if you notice how negative you is, your coworkers and higher-ups probably notice it as well. No one wants to promote the guy who bitches and moans constantly.

Don’t play along with his bullshit. Just ignore him and trust that at the end of the day, your positivity will beat out his negativity.

4. Openly mock him

If he still won’t stop, figure out a way to bully the shit out of him. Whenever he complains, just say “Wahhhh I’m Mike, I’m a baby” (assuming his name is Mike) and repeat back what he says in a baby voice while stomping your feet and crossing your arms. Simple but effective. When you’re with a group of coworkers and something good happens, just to turn to Mike and say “What’s wrong Mike? Can’t complain about this?” Give him a nickname like Bitch-boy or Coward. The more openly hostile you are, the better.

Bullying works. Don’t forget that.

Look at this loser complaining about a toxic work culture!!! What is he even talking about man??

When do your adult children move out?

Never. My favorite part of COVID has been people in their 20s moving home and being like “my parents love having me around! I’d totally move out, but I’m worried they’ll get lonely!”

I think your parents are going to be fine man. Sure, it was fun for like 3 months, but they’re also adults with their own lives. They’ve gotten the priceless experience to get to know their child as an adult and are actually not that happy with how you turned out. They already spent 20 years doing your laundry, cooking dinner, and cleaning up the kitchen while you play XBOX.

They do not want you there. In fact, they actually go to bed every night and argue with each other about whether or not they should kick you out. It’s tearing their marriage apart.

There’s a vaccine coming soon. Get an apartment.

Fav Taylor Swift Song?

From a nostalgia perspective, it’s really hard to beat ‘Our Song,’ but I know that’s kind of basic. I like her last few albums she’s put out. She’s really good at writing one-liners that just get stuck in your head. I had the line ‘you told your family for a reason…‘ stuck in my head for 3 weeks and I have no idea way, since I don’t even like that song that much.

Long story short, I can’t answer this one. I do want to shout out ‘Today Was a Fairytale’ because it’s from Valentine’s Day, one of my favorite Sunday wallow movies ever. Very underrated.

Why is our Washing Machine Leaking?

Ohhh look at me, I’m rich and have a washing machine. Fuck you man. Your washing machine is leaking because I came over while you were sleeping and smashed it with a hammer. You don’t deserve in-home laundry and I think that deep down, you agree with me.

Sorry about that. Had to get it off my chest. Happy Friday everyone!

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