7 Hollywood Personal Assistants Spill All

Illustrated by Sydney Hass.
Being a personal assistant can be a humbling experience. While there are certainly pros to a job that immerses you in the lives of the rich and powerful, it can also reveal the ugly side of humanity. Assistants see everything — from their employer’s daily schedule to their most intimate moments. It can feel like a roller coaster, with a boss acting like a demon from hell one minute and gifting their assistant an expensive bag the next.

Bosses everywhere have their quirks, but a town like Los Angeles — with its abundance of celebrities and moguls — can breed a particularly terrifying species. Being an assistant might as well earn you a degree in the psychology of human behavior. And while some former assistants would prefer to leave their traumatizing employment experience in the past, there are the ones who have felt scorned enough to write a juicy memoir.

Read on for seven scary stories from former assistants with bosses from hell, from a germaphobe actress to a Miranda Priestly wannabe. If you’ve ever been the assistant to an eccentric executive or crazy celebrity, find comfort in knowing that you’re not alone.
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Illustrated by Sydney Hass.
The Supreme Overlord
"I worked as an assistant for a boss who demanded she be referred to as 'Supreme Overlord.' She even had a memo sent out requiring everyone to stop whatever they were doing and address her as such whenever she walked in the door. Though [she was] in her 40s, full-blown childlike tantrums and belittling rants were daily occurrences. She cited Meryl Streep’s character in The Devil Wears Prada as her inspiration for running the company, but this was no Vogue; it was a niche clothing company! The staff was very small, so each employee was required to do many different jobs, but barely paid for the one they were hired for.

"Once, we all had to drive out to Vegas for a festival to work, only to find out that she didn’t pay anyone because she was vacationing in Hawaii and forgot. Many of us were young and lived paycheck to paycheck, and found ourselves stranded out of state in the desert on a holiday, which meant everything was closed.

"Our regular office headquarters were a warehouse infested with rodents and feces that reached temps of over 100 degrees with no A/C, except in her office, which was empty 95% of the time. In less than two years, four separate employees suffered physical and emotional breakdowns and were hospitalized, sometimes to find that their health insurance had been canceled due to the company not paying their premiums. Meanwhile, the 'Overlord' was making extravagant purchases like $1,800 sunglasses or $80K cars.

"The second-in-command was the real overlord of the company, though. She called the shots and was the 'creative' mind. Her 'creativity' included having staff stalk websites of other designers and companies to re-create their ideas while publicly accusing everyone in the world of 'stealing' her designs or strategies. Both the Overlord and her minion had large social media followings, so anyone who 'crossed' them or called them out on their horrible business practices would be put on public blast on social media. Everyone lived in fear of speaking up. This company also championed themselves as leaders in the body-positive, anti-size-shaming field, but at the office called people 'fat' and 'sloppy' and regularly made fun of their customers and fans."

—Peggy, 29
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Illustrated by Sydney Hass.
The Glamorous Germaphobe
"I was one of five separate assistants who worked for an A-list celebrity. In the six months I was there, there was maybe a total of three sentences ever said to me directly. The celeb refused to speak to anyone except for her main assistant, whom I’ll call 'Kat.' Kat had somehow been working for this woman for three years, which allowed her to earn the extremely difficult trust of our boss.

"One time, she asked Kat to ask me to go to Starbucks to get her regular drink, even though I was standing right next to them and could hear everything. She didn’t even look at me. I felt like a ghost. She was also a complete germaphobe. Everything we handed to her — including the coffee I had to get — would have to be double-wrapped in napkins so that nobody else’s hands touched it.

"We also had to keep hand sanitizer on us at all times, in case she needed to use it, which was constantly. She was also afraid to do anything herself and would have one of us wait outside of the door whenever she went to the bathroom. Kat would also have to sleep in the same bedroom with her if her boyfriend (another actor who was rumored to be a constant cheater) wasn’t in town."

—Sarah, 26
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Illustrated by Sydney Hass.
The Broke Producer
"The producer I worked for had to be 'walked' each day. This consisted of a two-hour hike through Bel Air, for which a woman — a 'friend' — was paid to accompany her. She would often leave for this all-important, everyday walk up to two hours late. As a result, every single meeting would be pushed later, until the whole army of assistants — which included me — was still stuck at her home, from which she worked, until 10 p.m. or later. That might've been okay, except that she frequently overdrew her accounts, which were allegedly kept full largely by a very famous media executive she'd had an affair with years before. Aside from her money made from 'producing,' i.e. bankrolling, at least one box-office success, a lot of the money [that] she wasted on the staff and various failed and failing development projects came from her ex-husband, a household-name producer.

"Somehow — perhaps [because of] all the surgery, staff, human growth hormone, and failure — she still managed to drain the accounts and would not pay her housekeeper for months. We assistants could usually argue [our] way to payment within three weeks past due, but sometimes not. And with the overtime you were working and gas you were buying to shuttle around and buy her a specific scented candle from Pottery Barn, the amounts owed were big money to young people getting started in life — the only people desperate and dumb enough to take this kind of job. The housekeepers were apparently thought to be less important and might go for months with no pay.

"The icing on that situation, though, was that a couple of years later, after the recession hit full force, I saw an article about how even in Hollywood, where image is everything, people were trying to not get stuck picking up a big bill for a group anymore. She was widely quoted saying she was always finding herself picking up the tab for her 'less successful' friends. I laughed out loud, not only because she was almost certainly the least successful of her friends and was often broke as a college student, but because if [only] it were somehow true and that was how she was spending her money while her housekeeper couldn't buy food for her family."

—Lauren, 32
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Illustrated by Sydney Hass.
The Bitter Birthday Ruiner
"After being an assistant for a variety of bosses in the film industry and corporate scenes, I started working for a woman who owned a huge PR firm. She’d always make snide remarks about her married friends and complain about her lack of love life. After seeing her roll her eyes when I told her I had a boyfriend, I soon realized it would have been best to keep that status of my personal relationships private.

"Knowing that I had a demanding job, my thoughtful boyfriend made sure to tell me three months before my 25th birthday that he was planning a surprise weekend trip for me. I asked my boss if I could have that weekend off and she said yes. Literally, at midnight the night before the trip, she texted me, saying she wanted her entire home to be remodeled, immediately. I was to be at her house the next morning with ideas and a list of famous interior decorators to contact and to try to get in the same day. When I reminded her that I had a trip scheduled three months before and that she had confirmed I could go, she simply responded that there was someone else who could take my job in a second. I honestly don’t think she would have done that if I had told her it was a family member or friend who had planned the trip for me, and not my boyfriend. I ended up just quitting."

—Kaitlyn, 27
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Illustrated by Sydney Hass.
The Drug-Mule Diaries
"I had the pleasure (sarcasm) of being the assistant for a rock star who was most prevalent in the '90s. My most insane task was basically to be his drug mule. He’d have me go all around town, picking up and delivering drugs. I was always scared shitless that I’d get killed by some drug dealer or arrested. But that’s not even the worst part.

"Sometimes, to mess with me, he’d have me dress up in costume to pick up the goods. One time, that included a full-on Girl Scout costume. I’m a dude, and yes, I still did it. He’d also have me scout goth chicks on Model Mayhem. I’d have to tweet to them from fake Twitter accounts and see if they’d want to hook up with my boss. As terrible as it sounds, he was always pretty successful."

—Mike, 27
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Illustrated by Sydney Hass.
The Manipulative Madam
"As a recent fashion graduate, I was excited to get a job as a second assistant to a high-level executive in the fashion industry. I figured putting in my time with a gig like this could help me make some good connections to really begin my career. At first, the work seemed easy. I mostly ran menial errands, made appointments, and attended shows and events. Then I was asked to come with her and the first assistant on a trip to Maui, which sounded awesome at first.

"During the trip, I realized that something was off. I assumed she would have a friend or family member come on the vacation, but it was just us three. She made us spend every single minute with her — every meal, every shopping spree — and we didn’t have any alone time. When she’d go to the spa (which was every single day we were there), we would have to be waiting for her right when she came out. But it was when we returned from the trip that things took a turn for the worse.

"She started complaining about the first assistant to me, in a way that seemed like she was waiting for me to respond with gossip, which I didn’t have because I never had problems with the other assistant. Then, during a performance review, she told me a bunch of things that the first assistant had supposedly said about me (like I was lazy, boring, and was out doing other things for myself when I was supposed to be running errands for her).

"I couldn’t believe it because I thought I had a pretty good relationship with the first assistant and considered her a friend. I decided to confront her. The assistant claimed to have never said those things and that in her own review, the boss had actually had similar complaints about me! She was clearly playing mind games with us, for some unknown reason. I knew I had to quit, but I was making contacts and actually learning a lot, so I was conflicted. The mind games continued, along with straight-up insults. She’d call me and the other assistant worthless, and that we would never reach success. I lost a lot of weight, developed a general anxiety order, and couldn’t sleep. I finally quit, and the other assistant did as well, shortly after. Worst job ever."

—Nicole, 24
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Illustrated by Sydney Hass.
The Cereal Caller
"I assisted a CEO of a company that makes movies. He called me 'Sweetie' with the frequency of a character in AbFab. People thought 'Sweetie' was actually my name because I was never called anything else.

"He would call my cell at 3 a.m., drunk, wondering where his cereal was or where the soy milk was (it was always in the fridge, mind you) and asking me to do impossible-to-accomplish tasks that needed to be done by morning. He would call at all hours and I would have to be available, no matter what. I once got scolded for not picking up his call because I was at a doctor’s appointment. He hated voicemail so much that he made a rule saying that his phone had to be answered after two rings. If anyone had to leave a message, I would get a lecture on how I should multitask better, even though I was answering calls for the entire company at this point.

"I had to shop for and prepare all of his meals as well as run his office and personal schedules while being the office manager for his whole company during a transition without an office assistant, so I worked around the clock. He looked for someone so I could be his assistant full time, and then he interviewed a girl who had no experience but was ridiculously gorgeous. He hired her, then told me she would be his assistant full time and I would get the lesser position in the office...and yup, you guessed it, I was still totally doing both jobs after she was hired! I put in my notice a month later, the day after another drunken middle-of-the-night 'Sweetie, where's my cereal?' call."

—Cara, 25
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