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Work Retire Mailbag Vol. 2 – Hooking up with Coworkers, Don’t Be An Annoying New Hire, and Email Signoffs

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.

Question: I’m starting a new job on Monday, which is nerve-wracking enough without the whole national pandemic and forced WFH going on. How do I make sure I’m not an outcast by the time we start going back to the office?

Answer: This is a tough one and I do not envy you. Obviously I don’t have a ton of experience with starting a job in a situation like this, but I can give some general advice on how to not be the annoying new hire and start off on the right foot.

Rule #1 – You have 2 months to play the “I’m new” card.

Take advantage of it as much as you can. Then shut up about how you’re new and don’t know how to do stuff. It makes you look bad. Just lie and pretend like you know what you’re doing like the rest of us.

Rule #2- Establish yourself right away

The first 5 assignments you are given, you need to go balls out. Then you can slack off once you’ve convinced everyone that they didn’t make a mistake hiring you.

Rule #3 – Go to the first 3 happy hours you are invited to.

Happy hours are a good time to learn about office politics, gossip, and find potential new friends. It’s also your chance to establish yourself as the cool guy who drinks a lot and falls asleep on the subway home. Don’t pass that up.

Rule #4 – Take notes when people explain stuff to you

My biggest pet peeve is when a new hire takes 30 minutes out of my not that busy day to ask me how questions and doesn’t take a single note. At least pretend like you care. It’s polite.

Rule #5 – Stop talking about your old job.

Trust me when I tell you that absolutely no one cares.

Rule #6 – Don’t criticize the way things have been done.

We get it, you have a fresh pair of eyes and want to change everything. You are going to turn this goddam company around. Keep in mind that your new coworkers are most likely not morons and are doing things a certain way for a certain reason. It’s ok to suggest changes but like chill the fuck out.

Rule #7 – Be normal

Just pick up on social cues and don’t be a little weirdo and you’re fine.

Question: What’s the best email sign-off? What does each email sign off say about you? Like everyone who says “cheers” sucks right?

I mean, cheers is horrible. Even if you were born and raised in the UK and have been living in America for one day, you are not allowed to say cheers in an email. Speak American and stop trying to have a personality.

Quick rundown on email sign-offs and what they say about you:

  • Thanks, —- normal, not trying to rock the boat, just here for a paycheck.
  • Thanks! — desperate, over-eager, extremely worried about people being mad at them just for doing their job.
  • Best – pretty fancy. Potential CEO.
  • Kind Regards – overly formal, stuffy, forces their children to wear a suit at dinner in their own home every night. Decent bar, terrible sign-off.
  • Please advise. – actively unhelpful, petty, vindictive.
  • Let me know if you need anything else. – God forbid you ask this person to do their job.
  • Humbly Yours – hilarious, insightful, stunning commentary on formal corporate culture.

My personal least favorite sign off of all time is a former boss who changed the automatic “sent from my iPhone” to be “pardon any typos – I’m tapping away on my teensy tiny little iPhone.” Really unsettling.

Unless your phone is this size, I am not excusing a single typo.

Question: What type of content is most annoying to see in quarantine?

Historians will look back on quarantine as peak content, and by peak I mean sheer volume, NOT quality. Lots of people have discovered passions and hobbies and are excited to share their experiences on social media.This makes me sick to my absolute stomach.

I hope after this is all done, we’ll collectively decide to never address what we all posted during this time. What happens in quarantine, stays in quarantine.

To answer your question, worst content has got to be step-by-step cooking on Instagram stories. Admittedly, I have zero interest in cooking and can really only make 5 things:

  1. Spaghetti
  2. Spaghetti with red
  3. Chicken
  4. Chicken with red
  5. Spaghetti, chicken and red.

But I can’t fathom how anyone is interested in this The cooking blogger market is saturated enough as it is – why would I want to watch a 29 panel Instagram story of someone I had one class with in college make chicken picatta? It’s literally just you stirring a pot, adding some spices, and doing some boomerang thing as you take asparagus out of the oven. I can figure it out on my own.

Honorable mentions include educational content about coronavirus (I’m on social media to escape COVID-19. If I want information I’ll go to the news,) any sort of Instagram challenge, anything with the caption ‘what day is it again?’ and literally every single piece of brand advertising.

Question: Is it ever OK to hook up with a coworker? What are the does and don’ts? Also, does the phrase “don’t shit where you eat” apply to this situation? I say yes but friends have said no. Please deliver a ruling.

It is 100% ok to hook up with a coworker. In the adult world, it’s almost impossible to meet new people in an organic way, since everyone is mean and busy. Office romances make a ton of sense, since you naturally have a lot in common with your coworkers and see them every day. Outside of being able to talk shit on your office, you’re also the same age, level of intelligence, have similar interests, career goals, and you make roughly the same amount of money. But you need to tread lightly.

Do’s and Don’ts

  • DON’T – tell anyone in your office (or try to limit the people who know to as few as possible.) The risk is not worth the reward, and plus you don’t want to be the type of person who hooks up with someone and tells the entire world.
  • DO- be prepared to have a conversation. Office hookups really only work in two situations – very casual or very serious. Once someone catches feelings, you either need to cut it off or try to date date. Can’t have that ambiguity with someone you see every day.
  • DON’T – hookup with your boss or an intern. Avoid anyone in your department or direct team, but things happen.
  • DO – try to see them outside of work events. It’s fun to sneak off from a work happy hour and all but that’s asking to get caught. Much better to send a 2 am ‘you up?’ text that they won’t respond to and then have to face them on Monday morning.

Finally, there’s the excuse – “I don’t want to date a coworker.” This is the perfect way to keep a casual thing going that you have no intention of making serious. Except it’s pretty much bullshit.

If you like someone, the fact that you work with them truly does not matter. That goes for pretty much any excuse people give for not dating someone . If you actually like someone, you will make it work. Even if they are someone who posts step cooking stories on Instagram.

Don’t do this. That ginger guy is 100% going to see you in the reflection of his monitor.

Question: All my coworkers are cold as fuck and never initiate any small talk before or after meetings. Any solutions?

That sucks. I love small talk. It’s honestly soothing to me. It sounds like you might work in something with a lot of boring nerds like tech or accounting or something. Or they maybe just don’t like you? Their loss bub!

Chances are, they may just be shy and not in the mood to talk, in which case you need to drive the conversation. Luckily for you, we’ve put together a helpful how-to video on small talk tips when we’re all back in the office.

Or just quit.

Question: With WRD smashing the 10k-follower glass ceiling, I can’t help but think you’re heading for a classic catch-22. On one hand, WRD amassing a following of millions of cube-jockeys across the world sharing in a laugh at their mundane and cliché existence would be a good thing – you’d be famous and rich and have access to more comedic opportunities than you’d ever thought imaginable. But on the other hand, the fame and notoriety would corrupt you and your perception of office life, distancing you further and further from everything that WRD stands for. Or, is that the point? That no matter the glitz or the glam or the glory, we all work retire and die? That the connected fabric that runs along the corporate ladder and beyond are these crude totems of existence? That even when attaining the zenith of one’s personal fulfillment and development, it’s the acknowledgment and embrace of these doldrums that make us most human? Also what’s your favorite Jersey Mike’s sandwich?

Original Italian on Rosemary Parmesan bread. Hold the tomatoes.

When the readers try to get me to confront existential crises

Humbly Yours,

Content King

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