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A Man Asks the Obvious Obviously

I want to ask out this woman at my company. She’s junior to me, but doesn’t report to me directly. Is there a way for a man to ask out a younger woman at work without coming across as sleazy?

— Anonymous

You must be real pruned-up from spending the entire last year in an isolation tank. The only circumstance in which you can ask this woman out is if she sends you a literal ink-on-paper invitation to do so, like, in calligraphy and maybe with a seal stamped in wax, which would be awesome. (Also might mean she’s a vampire?) But, sure, you can totally ask her out if you don’t care about (1) her security about working with men in any capacity forever or (2) your career! Then have a blast, cannonball as many lives as possible on your way down the trash chute.

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Pivot to Socialism

I work for a newish company that keeps “pivoting” and recently laid off a bunch of people. Now my co-workers want to unionize, and I don’t know how I feel. I care about the company and want to see it survive. I know that it’s “business, not personal,” but something about getting involved in the union feels deceitful to me, and I worry that it will hurt the company long term. My co-workers have good reason for wanting to unionize, and I feel weird not supporting their efforts, but at the same time, what’s the point of negotiating for better hours, pay and benefits if it hurts the company’s bottom line so much that it has to lay off more people?

— Anonymous

You can probably table your feelings about this for a year. But if the office gets there, honestly, whatever “demands” the organizers start to make aren’t going to be what hurts the company. (A 2 percent across-the-board salary increase? Oooh, scary!) Companies destroy themselves because they’re greedily managed, their ideas about business are bad, their pension plan was managed by morons or they ignored someone starting to eat their lunch. It’s not about better dental. Go talk to some folks who work in union workplaces! I work in management in a union shop and love having an organization protect the rights of my colleagues. What multiplier of your salary does the C.E.O. make? If the company is struggling and it’s more than triple, maybe you’ll join them on the red ramparts. Disturbing news! You may not have to worry about this. Dollars to doughnuts this company is going to be a whole lot slimmer before the union gets certification. That slimming may include you.


The Office Sacrifice Is You

The C.O.O. of my company is a power-hungry nerd. He’s the worst. No one at the company respects him, but he’s super-organized and handles all the logistics that no one else wants to deal with, so people keep him around. He’s not technically my supervisor, but since he sets up all the most important meetings, he gets to decide whom to include in major company conversations. He’s always leaving me out of meetings and off important email chains, and for some reason really hates me, even though I’m much nicer to him than most of the other people at the company. What do I do? I don’t like the guy, and don’t really care what he thinks about me, but I feel like my career is suffering because I never know what’s going on.

— J.B., Los Angeles

If you’ve ever watched a horror movie, you know that the star psychopath wins mostly because he’s playing by psycho rules and the victims are playing by normal-people rules. So your office Michael Myers comes knocking at your front door and you invite him in for tea. Every day he’s stomping all over you! Yet here you still think he’s like you on the inside. He’s a Murderbot 6000. He’s a misprogrammed goon who’s out to get you. Let’s talk about your choices! You’re “nicer to him” than everyone else? You’re acting like the office is a day care center and it’s time to share blocks, yet this guy is running around with a chain saw. Tell him firmly, once, what you need. Second time, send an officewide email that says, “Babadook here keeps ‘forgetting’ to add me to these meetings, can you help him remember?” Third time, roll up on his office and start straight-up yelling. It’s time to misbehave. Because you’re a nice person (by which I mean you’re a professional victim and probably need other kinds of help), you’re going to have to over-index on the mean levels. Hurry up.


I Said I’m Not Thirsty

Who are the people who organize after-work happy hour? I have never been one of those people and never know what to make of them. Sometimes I envy their enthusiasm, and other times I think they’re sort of pathetic? I know that’s cynical of me, and that’s why I’m trying to better understand. What compels someone to become the office social coordinator?

— Ben, New York

As it happens, I have one of these! I asked Anya Strzemien to explain why she makes me leave the office to socialize every month. She said: “Anyone who works in an office knows that they are the most awkward places on earth, and all previously acquired social skills evaporate upon entry. Most good has come to my career via relationships, and relationships don’t grow as naturally under fluorescent lights. That’s science. Hence getting out of the office to see your colleagues in a different light — literally and figuratively — and maybe talk about something that’s not work. (My colleagues also seem to love games with balls — bowling, Ping-Pong, Skee-, etc. — which is adorable and sort of pathetic, too.) It’s an investment that I think pays off back in the office. And by putting these happy hours on my personal credit card I now have all kinds of points, so I can’t pretend it’s entirely virtuous.”


This Is Obvious to Everyone You Know

My wife and I have been paying off our student loans for years, but we still have about $75,000 to go. She’s 35 and really wants to start having a family, but I think we should wait a few more years, until we’ve paid off more of our loans. We argue about it constantly.

— Anonymous

You don’t actually want children and you’re wasting her time and she will hate you forever.

Choire Sicha is the Styles editor of The Times.