Work.Retire.Die.

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 workretiredie@gmail.com 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.

Work Retire Mailbag: Volume 6

Is 6 months too soon to leave a job?

Absolutely not my friend. There’s this expression I made up that goes “when you know, you know” which can apply to dating, Uber drivers that immediately give off “I want to talk to you even though you’re wearing AirPods” energy, and jobs that are a bad fit. Don’t waste your already mediocre life on a shitty job situation just because you’re too afraid something will look bad on a resume. Quit that shit!

HOWEVER – the one caveat to this whole answer is that you need to speak up at a certain point, around 2 months into the job. Voice your concerns in a professional way to your boss. Maybe grab coffee with another employees you trust to see if this place really sucks or if you’re maybe just being a psycho. Give it some time to get better and see if you’re happier once you get the hang your new environment.   

By 6 months though, you’ve given this thing a fair shot. Sure, it’s not going to look incredible on a resume that you left a job after 6 months, but people will understand in an interview. It’s very easy to stick around too long, get Stockholm syndrome and convince yourself it’s not thattt bad here. Trust me, you don’t want to end up like this guy.

How many promotions before you’ll delete this account?

There’s not enough promotions in the world pal. Realistically, if I’m working, I’ll never delete this account. I don’t see a world where I don’t hate (or at least getting annoyed with) the concept of working for a living. It sucks, I’m sorry, and anyone who likes working has a broken brain from watching too many Gary V videos.

Now, if I can afford to not work? Guess what? We are transitioning into the retire phase of this account, which will be shockingly wholesome and mainly content around bingo night and when your yacht breaks down or something. It’s gonna be sick.

How do I approach asking for a demotion?

I love this question. Honestly, fuck promotions. Most of the time, it’s just a title change and an extra $21 on your paycheck in exchange for a shitload of work, responsibility, and anxiety that you just don’t need. If you’re at a company you don’t like or in a field you don’t see yourself working in long term, then keep your little head down, collect a paycheck while doing as little work as a possible, and plan an exit strategy.

Asking for a demotion is a bold move, but one that I embrace. Keep in mind though, that when you do this, it is really going to sabotage your standing at the company (which is totally fine if you don’t give a shit.) It reminds me of a situation in my first job when my company announced they’d be doing layoffs in a few weeks and my 22-year-old coworker went to HR and volunteered to be laid off in exchange for a healthy severance package. My dude, that’s for the people who have been there for 40 years, not you.  Needless to say, as someone who was actively trying to leave the company, that coworker was decidedly not on the promotion fast track.

Anyways, I don’t think it’s unreasonable to go to your boss and say that this job is too much for you and you’re feeling overwhelmed. They might even let you keep your job and just transition some responsibility off your plate. Or they’ll give you your demotion and you’ll just start being a little less stressed and a little more poor. Either way though, you should start looking for a new job because it feels like this company or department just isn’t for you.

Is this it? Really? I have to sit in front of a computer for the next 40 years and then die old?

Yes! Unless you get a standing desk. Or they invent something that’s not computers. You’re probably not going to die old because you don’t exercise and you did way too many Whip-Its your sophomore year of college, but who knows! You might get lucky.

Either way, this is definitely “it.” And that sucks. But also, it’s fine? What else did you want to do? Work on a farm? Build something with your hands? Contribute to society in a meaningful way? Get a grip bud.

Life is a meaningless slog towards death with brief moments of joy sprinkled in justtt frequently enough to keep you going (the perfect pair of jeans, successfully playing the name game at a party, open bars, you and your coworker realizing you hate the same person at work, entire row of an airplane to yourself, thinking of the perfect comeback, a good soft pretzel, etc.) Embrace it.

Why do I go to the office just to sit at my desk and take Zoom calls with a mask on?

For camaraderie, your company to justify their office real-estate cost and the chance to spend $19 on a salad during lunch.

I accidentally said “ok bye, love you” to my boss when I was leaving a Zoom call. Can I ever show my face again?

Yes, you can. But not without doing some significant leg work because you have jeopardized the most important thing in any business relationship: trust.

Your boss needs to believe that when you say something, whether it’s that you’ll have a project by EOD, that you can handle more work or that you definitely have your third doctor’s appointment of the week and aren’t interviewing for a new job. You don’t want your boss to think you’re a liar, do you? That’s what I thought.

It’s time to convince your boss that you really do love them. In a romantic way. I don’t care if they’re ugly, married or the opposite gender that you’re attracted to. Throw your sexuality and standards to the goddam wind and begin a long con to win their trust back. Send them flowers. Write them long winded, tear stained love letters. Make meaningful eye contact whenever possible. Start openly criticizing their spouse in a way that is deeply personal but also based in a truth your boss is too scared to confront.

Of course, like any good lie, you will need to believe it on some level. Soon, you will actually develop very strong feelings for your boss, which is extremely healthy and normal long term approach to happiness and professional success. If they don’t feel the same way, sue them for sexual harassment. This will be the grand romantic gesture they needed to realize they actually do love you back and you’ll ride off into the sunset with your heart full and your career intact.

If you don’t want to do that, I’d recommend just quitting on the spot.