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At Happy Hour, Kindergarten Rules Apply




There is nothing wrong with being an executive assistant, of course, and there are plenty of people who have long and fulfilling careers doing it. But you, E.S., are not going to be one of them whether you stick with it or not. My arithmetic says you’re roughly 30, and you already are so burned out on this career path that you only “reluctantly” took a new job. Good jobs are not lifesavers, but bad jobs sure are life ruiners, so you have to get out of executive assisting — and quickly.

The good news is that you now have the perfect opportunity to pave the way toward something else. Don’t worry about applying too quickly after you were hired; the timing will never be perfect. When a firm hires a new employee, the very best-case scenario is that the employee outgrows her job responsibilities, moves onto something else within the company and continues until she’s running everything. This could be you, E.S., but only if you apply.

I’m a woman in sports media and you’re a woman in the tech bro dystopia that is modern-day San Francisco, so I feel uniquely qualified to advise you on all the things that could go wrong here. They could tell you it’s too early to apply for other jobs, or you could be rejected for other reasons, valid or less so. You could be condescended to when you express interest in the job, patted on the head and told to go back to assisting. You could be actively or passively discriminated against until you see no choice but to leave your job and reluctantly take yet another assistant gig. Those things could happen, and they do. But what if none of them happened? What if, when you told your boss you’re applying for the open position, the response was “I didn’t know you were interested in that — let’s get you in for an interview”? Not to go all “Lean In” on you, but you’ll never know unless you ask. So apply for the job, and if you don’t get it, apply for another one. Better yet, apply for a dozen, at all different types of companies, and keep applying till you get one. And then, years from now, when you’re running your own department or company, don’t forget to ask your bright-eyed young executive assistant what she’d really like to be doing.


I recently found out that one of my co-workers blocked me on Facebook, Twitter and Instagram. We work in a big company, and although I recognize his face I never spoke to him (or about him!). It kills me that I have no clue what drove him to such bizarre behavior. As we are scheduled to work together on an assignment next month, should I confront him about it?

— Tel Aviv

No. No!

Blocking a co-worker you don’t know is a weird thing to do. An even weirder thing to do is to digitally stalk a co-worker you don’t know to investigate whether you’ve been blocked. But the very weirdest thing to do is to confront a co-worker you don’t know with the results of your investigation. Never, ever mention it.

That’s my Semiprofessional Advice Columnist advice, anyway. Would you like to know the brilliantly petty thing I’d actually do? Take a bunch of cool photos while you’re working together and ask for his handle so you can tag him. Then Instagram his reaction.

Megan Greenwell is the editor in chief of Deadspin. Write to her at

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