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Don't take candy from strangers, even at work

I work at a casual startup with no set T/O policy. While this may sound like a dream, it can actually be quite confusing at times. Should I just request time off until someone tells me to stop?

—Haggard, Roscoe Village

Does your company’s time-off policy involve a headless minotaur chasing you through a water park while flawlessly chanting your Bar Mitzvah portion, night after hopeless night? Because if it doesn’t, then it doesn’t sound like any dream I’ve ever had.

As recently as 2007, nobody had ever heard of unlimited vacation time. Then the folks at Netflix let their salaried employees take off whenever they pleased. Later on, they won the Internet. Ever since, unlimited time-off policies have become trendier than Elon Musk in a mullet skirt.

And here’s the sneaky thing. Everyone is like you, Haggard. They’re confused, they don’t feel entitled to their vacation days, and as a result, they take fewer of them, all while feeling pressured to be grateful for their great benefits. Meanwhile, companies aren’t legally obliged to pay out for vacation days accrued when they fire employees because nobody accrues vacation when they have an unlimited supply. It’s a perfect storm.

“I’ve seen some companies put off clarifying the time-off policy because people work more without one. If the founder or key team members work 65 hours a week and skip vacations, then when you work 50 hours and take a long weekend, you feel like a slacker,” says Haydn Shaw, author of “Sticking Points: How to Get 4 Generations Working Together in the 12 Places They Come Apart.

Without articulated boundaries, we inevitably tend to overcompensate, especially in a startup atmosphere, where everyone thinks that working 80 hours a week in a hoodie makes you totally laid-back. All of which brings us to your question.

“If your startup is large enough to have four or five different managers, they will inevitably give different answers to the question of what’s acceptable time off. That always creates resentment in the people whose bosses are more demanding,” Shaw says. “In either case, graciously ask for clarity. You’ll help yourself and your colleagues.”

Unlimited PTO is like that professor who refuses to assign page-lengths for essays, urging you to “take as long as you feel you need to.” If your manager gives you a similar cop-out, ask whether you’d be allowed to revert back to the old system. That’s a conversation worth having.


There’s a man in my building who gives out candy to young women when they walk by his office. He once withheld candy from my male co-worker, saying it was “for women only.” I don’t agree with any of it, but I do love a piece of chocolate in the middle of a long workday. Is it wrong to take the candy???

—Emily in Logan Square

While it’s hard for me to imagine a situation where accepting candy from a strange old man could go wrong, I’ll do my best.

Stop taking the candy. Now. And forever. Or at least until the day when men earn 75 cents on the dollar and the term “glass ceiling” is hooked up to a ventilator and Mark Zuckerberg is the one getting endlessly peppered with questions about work/life balance, you’d be wise not to endorse sexism in the workplace.

“The same thing happened in my office; now all the females who took the candy are toothless and fat. Productivity is vastly increased because none of the male workers are distracted by them,” says Erin McLaughlin, whose tenure in Fordham’s career counseling department has sharpened her sense of humor. “In all seriousness, this man’s predilection for bias could cause a major rift in your building and discrimination should not be tolerated — stock up on your own supplies.”

That’s the great thing about your dilemma. IT’S NOT A DILEMMA. Last year, Americans consumed more than 3 billion pounds of chocolate. You’re talking about offending your male colleague and taking a hacksaw to your worldview in exchange for one of the most common products known to man. If your question were, “This sexist old man down the hall is handing out Fabergé eggs — do I take one?” that would be a legitimate quandary.

We all have our price. A Hershey’s kiss isn’t it.

Got a question about how to act around the water cooler? Tongue planted firmly in cheek, we’ll find an adult to answer it. Email us at advice@chicagogrid.com.