This summer Netflix released the most honest film about what it’s like to work for a horrible boss since, well, Horrible Bosses. The beloved romcom Set It Up. tells the tale of Harper (Zoey Deutch), who is the assistant to Kirsten (Lucy Liu), a high-powered media impresario in the vein of The Devil Wears Prada‘s immaculate Miranda Priestly.
In one especially dark sequence, Harper runs around the office wearing Kirsten’s Fitbit—so she can hit her desired 10,000 step count—and has to order “that thing Kirsten likes from that place with that delivery guy” for Kirsten’s 11:00 PM second dinner. The film paints a dismal picture of what it’s like to work for a difficult person—but as the expression goes, real life is stranger than fiction. The tasks Harper is asked to do in the movie don’t hold a candle to the stories we heard while talking to the assistants and caretakers of the rich and famous.
To deliver the ultimate guide in how to tolerate impossible coworkers, bosses, friends, and relatives, we spoke with the assistant who used to fetch Oreos for Khloe Kardashian’s impossibly ‘grammable cookie jar, the Upper East Side nanny who assisted in a parent’s weed delivery, and the Below Deck star who had to import a particular brand of nuts (from another country!) for a client while she and her crew were on the high seas. Below, their their wildest, weirdest stories—and their best advice for how to deal with difficult people.
Former Assistant to Khloe Kardashian
“During my time working for Koko, a lot of my job was to go grocery shopping. If you’ve ever seen Keeping Up With the Kardashians you know what immaculate kitchens the sisters have, and I was in charge of stocking up on the snacks, or what I like to call “prop food.” I remember one day in particular when I was tasked with buying organic fruit for a scene they were shooting in Khloe’s kitchen.
“At first, I was asked to buy fresh, organic pineapples (which were, of course, out of season). After driving 45 minutes to a farm on the outskirts of Calabasas I was able to procure the pineapples. But as soon as I returned to the house, I was immediately sent back out—without so much as a thank you—to purchase another out of season fruit, plums. Being in charge of tracking down hard-to-find foods was frustrating and often felt fruitless (pun intended), but I had to remind myself that even the small things that I was in charge of that seemed banal were all a part of the larger operation. Even if you’re doing something thankless and aren’t getting that “thank you” from your boss, know that you’re making their life easier—and day go smoother—and for that they’re immensely grateful (even if they don’t tell you).” — Anonymous, Los Angeles
Divorce Mediator
“As you can imagine, people are often not at their best when they are going through a divorce. I’ve learned to be compassionate, and to try to get a sense of what they are experiencing. It often involves a lot of fear of the unknown, of transitioning into a new life, and grief for the relationship they had (or thought they had.). I work hard to understand them, and to acknowledge their reality, while helping them stay positive and mange their emotions so we can keep the conversations we have during mediation positive and productive.
“When you’re working with highly emotional people, help them parse through their feelings. When people are upset, they can often express their feelings in an unhelpful way, like yelling. The best thing to do in that scenario is help your client find a better way to articulate what they want and need. You can even do this in subtle ways, like asking them simple questions to calm them down and get to the root of the problem. It will be better for you—because nobody likes getting yelled at—but also will help them get what they want much faster and easier.” — Joy Rosenthal, Rosenthal Law & Mediation, New York
Upper East Side Nanny
“Working for the elite families of New York City is a balancing act. On any given day, I’m expected to fill in for wealthy Upper East Side moms as they go to their boutique fitness classes, tennis lessons, or lunch meetings. That leaves me to pack snacks, cart along book bags filled with art projects and chapter books, and make sure we arrive to any activity the children might have that day. While that in and of itself is difficult, I have found it even more challenging to meet the demands of the difficult mothers. From having my bosses ask me to stay “a little late” while they head out to a party (only to be woken up at 4 AM), to picking up flowers for a bris ceremony, or being asked to check three stores for a specific brand of pasta for a two-year-old, my days are never boring. I’ve even been asked to use my discretion after watching parents meet with their weed delivery person in their son’s room!
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