Confessions of Celebrity Assistants: What It's Really Like to Work for Hollywood's Rich and Famous

The first rule of Fight Club is you do not talk about Fight Club. 

I'm sitting in the lobby of the Players Club, in Manhattan's Gramercy Park, waiting to meet my interview subject. She is a longtime celebrity assistant, a profession that is both hard to find and incredibly difficult to convince to talk to you about. I'm in the lobby because in order to walk past the entrance of the Players Club you have to be escorted by a member, and I'm waiting because her principal, which I will later learn is a fancy word that celebrity assistants use to describe their bosses, landed after a long flight with a laundry list of things he needed to talk about immediately. 

It's during this time that my mind starts to wander to that classic and brutal Brad Pittmovie. 

The Players Club reminds me of Fight Club, if Fight Club took place in a Gothic revival mansion facing the only Manhattan park so exclusive that one needs a key to enter. And replace the barren cement walks with dark wood paneling and the dirty floors with patterned carpets reminiscent of the set of The West Wing. And also, I had just spent weeks trying to penetrate the inner circle of Hollywood's inner circle, so the connection felt natural at the time. 

What I would learn over the course of several weeks and interviews is that being a celebrity assistant is so much more involved than I thought. It's part Devil Wears Prada and part The Proposal and part The Office and, luckily, not at all like Mad Men. Celebrities are intensely private and as such their assistants are intensely private. This is where I note that some identifying details have been changed here to protect any future careers and also to save the celebrities themselves from embarrassment. 

The second rule of Fight Club is you do not talk about Fight Club.

What most people want to know first about someone who spends their days next to Hollywood's biggest talents is: How did they get there? As it turns out, it's purely by accident. Most start off with at least a peripheral interest in the entertainment industry, whether that means having aspirations to be a filmmaker or to work in communications. Most take a job because, when you're 22 and living in New York or LA, a job is a job. And then one thing leads to another, a former boss puts you in touch with a new contact, and suddenly you've spent years doing something you had barely heard of.

"I didn't know this industry existed," says Kelly Engstrom, who has spent the last few years as the right-hand woman to former talk show host and Oprah contributor Nate Berkus. "I didn't know that [being a celebrity assistant] was a job you could have. I went to school for communications so I thought I would end up in PR."

That sentiment was echoed several times. One assistant did a semester at NYU's film school and using connections she made there, wound up with a post-college gig working for a prolific director and spending her days on the set of The Sopranos. Another was given a random referral and the next thing she knew was moving across the country to live in Malibu and assist an actress right after her first Oscar win. (A move that, it's worth mentioning, wasn't revealed until she accepted the job.) These placements are so random that the assistants could barely give advice to aspiring celebrity assistants if they tried. "I don't think any of us go to college and say, I'm going to be a celebrity assistant," stressed one person. 

What isn't random is the interview process. It starts with full privacy measures to protect the identity of the celebrity—the principal is never revealed and, typically, neither are other details. When Engstrom she received the call for an interview with The Nate Berkus Show, she didn't even she had applied to that job. 

"I remember the posting being very, very, vague," says another assistant. "I replied to a random Gmail account and there was no connection to [the actress]. I didn't know who the job was for, for a long time, and there were several vetting stages and then finally my second-to-last interview was with her current assistant, who I was going to replace. They were holding things very close to the vest, but with good reason—it was really the height of her fame." 

Sometimes even the star's current staff is kept in the dark until the last minute possible. During another interview process the posting advertised that the assistant would be required to move to Milan, but that was it. The candidate went through a very private vetting that took almost six months and when she arrived for her first one-on-one with the principal even the current assistant didn't know that he was about to be replaced. The big reveal played out in truly dramatic fashion: "She [the principal] was staying in this very luxurious suite at the Waldorf Astoria and I was escorted into this huge, dark wood living room filled with flowers and this wonderful scent. Here on this floral sofa was this tiny woman with striking long hair and huge eyelashes. I felt like I was in a movie."

If this is your first time at Fight Club, you have to fight. 

Once celebrities' assistants are hired they're almost immediately whisked into the fold of their hectic, yet completely glamorous, lives. Like the time that Berkus' assistant crossed paths with Oprah. Or the time an assistant was whisked away to accompany a family vacation in Lake Como.

But before all that, you have to take care of business. The first step of the on-boarding process is signing a non-disclosure agreement. This puts the principal at ease, of course, but it also fast-tracks the process of earning, and building, trust. 

Every star has different boundaries and there are certainly those who try to keep their personal information private from their team as long as possible, but more often than not the assistants have access to almost everything in a matter of weeks. Past assistants are usually gone well before the new one starts so on-the-job training is exactly that: on the job. One assistant described it as "trial by fire," that relies more on your emotional IQ than anything else

The second thing that most people want to know about someone who spends their days next to Hollywood's biggest talents is: What kind of luxuries are you treated to? The answer is, in a nutshell: less than you would think. Call the job more glamour-adjacent than truly glamorous. There is travel, of course, often shared by other members of a principal's team like a manager or agent. 

"If Nate is doing appearances in New York I don't have to go because his publicist is there, but I'll go along for book signings or appearances," says Engstrom. "The level of luxury for my travel depends on who's paying: Sometimes in the contract they allow for two first class tickets, so that's when I get to do it. If Nate's paying I don't typically travel first class."

That seems to be another pattern across the industry: Assistants aren't going to be treated to expensive things, but they're also welcome to accept them if they're free. Engstrom adds that Berkus will always try to get her upgrades to join him in first class, and other assistants told me that they learned quickly how to negotiate their way into more luxurious travel. 

"My bosses would always buy my flights if we were traveling, but I wasn't living the high life the way they were," one assistant explained. "Instead I learned how to use my relationships with their vendors, like airlines or limo companies, to get freebies. I bring them all sorts of business from my boss, so if my mom is coming to visit I'll ask for a free town car." 

Another assistant explained that the system isn't nearly as unfair as it may seem: "I still stay in nice hotels, even if my room isn't as good. I'm not staying at a roadside motel while he's at the Four Seasons—we're always at the same place."

And for some, the perks extend beyond the tangible into the personal. Those who are really lucky find a friend as well as a boss in their principal—Engstrom says she and Berkus are "really, really close." They attended each other's weddings (another opportunity to bask in the presence of Oprah) and he was the first person in the hospital when her daughters were born. She's also been able to bear witness to the behind-the-scenes of his famous design projects. 

"We worked on Karlie Kloss' apartment in New York a few years back and I got to be very hands-on because I was the one person on-staff in New York," she gushed. "I would be there so she wouldn't have to fly someone in to, like, meet the drapery guy. She was the most generous, lovely person and it was a really great experience to see that from the start all the way to the end when it was shot for Vogue."

But it's not all rainbows and unicorns and first class upgrades. There is a decidedly dark side to dedicating your professional (and most of your personal) life to the members of Hollywood. It's crushing. It's exhausting. It's pandering. It's learning the many personality quirks and emotional instabilities of a group of people whose entire livelihood and self-worth lies in whether or not the world likes them. It's nowhere near as bleak as the worldview of Tyler Durden, with his rambling speeches in the basement of Fight Club, but he was on to something when he said, "We've all been raised on television to believe that one day we'd all be millionaires, and movie gods, and rock stars." To be duty-tied to someone during that process isn't easy. 

Sometimes this plays out in a rather banal way, the usual mix of stress and frustration that can befall any boss after they've had a long meeting or a terrible travel day. Assistants who are in healthy celebrity-employee relationships cite that the hardest parts of the job come when something happens that is beyond everyone's control. Or they'll mention the digital toxicity that involves being tied to their phone all day, looking at their texts being the last thing they do before they go to sleep and the first thing they do when they wake up. 

Sometimes they lament that their typical day is dictated by whatever it is that the principal wants to do that day. Or that there is no true office structure or sometimes even an office. They do their jobs in the celebrity's kitchen or in the celebrity's hotel suite or in the celebrity's limousine on the way to the bathroom or while the celebrity is getting a blowout. Life is lived constantly chasing after someone who doesn't have time to stop or even respond to an email. To be a celebrity assistant is to realize that talent only texts. 

Sometimes the business-like nature gets overwhelming. One interviewee said that she was currently aware of three lawsuits that her former bosses were involved with. (An NDA is nothing to be screwed with.) And a surprising amount of an assistant's job is to get discounts and freebies for their bosses. Whether it's a home contractor or a clothing designer, or a five star hotel that the assistant needs to convince should give them a discounted VIP rate and a complimentary upgrade of two or three categories. 

And sometimes it gets just plain weird. Like the aforementioned Oscar-winning actress who has tasked her assistants with tracking down gourmet cooking ingredients in the middle of the night because she suddenly decided she absolutely had to spend the following day making an elaborate dish. Or the principal who cared so much about the birds who landed in her yard that she instructed her assistants to hand-make them food. 

Stars have incredibly large teams consisting of stylists and makeup artists and personal trainers—and while that builds a great network that assistants can rely on to figure out how a celebrity likes things, it also means that at any given moment someone is looking for them. One assistant told of spending a national holiday on a desert vacation with family only to get a phone call on the top of a mountain from the actress' tennis instructor, wondering why she didn't show up to her scheduled lesson. Everyone I spoke with was realistic in the expectation that working for a member of Hollywood involves some hard labor, but many described certain tasks as simply going too far. 

After a few years in the business personal assistants begin to understand celebrities in a way no one else does. They begin to see inside the belly of the beast and their analysis of the industry often sounds like it's coming straight out of a therapist's notebook. They've learned that the air is so thin at the top of Hollywood that everyone knows each other. That it takes something in your DNA to become famous. That (almost) all celebrities are brilliant. That they share the exact same peculiarities. 

They've learned that the business is so intensely appearance- and youth-focused that stars develop the same taste in plastic surgery. That the surest way to get realistic-looking eyelashes is to use mink. That there is no point in being shy in this business because you will inevitably have to hold a meeting while your boss is in her bathrobe. 

They've learned that even though they have all the money in the world they're still focused on their bottom line. That they will go to great lengths to contest a bill they don't want to pay. That stars are so averse to doing chores that often a personal assistant isn't enough; they hire house managers to take care of the rest. That often times the worst treatment comes from other members of a star's team instead of the star themselves. 

Fights will go on as long as they have to.

I've learned things too. I've learned that celebrity assistants are immensely proud of the work they do. That they get satisfaction in every win and live for the delicious feeling of satisfaction that comes from crossing off something in a to-do list. That as secretive as the industry is, they love to talk about their work. That they're constantly hit up by friends and family who are fascinated with what they do, and that they are fascinated by that fascination. 

I've learned that most of them are totally stuck in this business. That the longer you're in, the harder it is to get out. Celebrity assistants get paid handsomely for their services, as they should, but that means that the temptation to stay is strong. If they wanted to quit and pursue the career in journalism or directing that they initially set out for it would involve a drastic pay cut. Some assistants, like Engstrom, are lucky to have bosses that foster their talents and skills—She is also the co-head of the digital team and oversees Berkus' website and social media. But others don't have a clear post-celebrity career path. 

I've learned that most assistants also do not want their boss' jobs. They don't have aspirations to be famous. They don't want to be on TV or in movies. 

I've also learned, of course, about the rules. 

The world of celebrity assistants doesn't just feel like Fight Club to me, it feels like Fight Club to them. And the rules are way more specific. There are actually several clubs that are designed specifically to help out with, and occasionally keep the secrets of, people who work for huge stars. Like the New York Celebrity Assistants, which was created to offer a safe space for those who devote their lives to Hollywood's elite to network—and much more. 

It's a group that allows them to ask each other everything, to gain instant access to hundreds of other assistants and their Rolodexes. "It was like the clouds parted," describes Engstrom of gaining access to the group. "If you need someone who has a direct contact for flowers in Milan or can get you into the hot restaurant, you can find them. We can also talk amongst ourselves about salaries and career advice so it's a safe space to be open about anything you're dealing with at work."

That's where the rules come in. No one shares anything with anyone without permission. If someone is trying to get in touch with Nate Berkus' assistant, someone else will need to ask Nate Berkus' assistant if that's okay. Everyone in the club is bound to an NDA. That doesn't stop them from talking about their experiences but it does make them extra paranoid about being confidential or detailed or sharing too many facts. Most assistants have a few friends that they might tell a little bit more to, as with anything in life, but they all attest that nobody has ever crossed the line. 

It's not just the assistants either. There are organizations for the house managers of celebrities and probably nannies and babysitters and anything you can think of. As one person told us, there is a whole underground web of people who make things happen for celebrities that most people don't know about. 

Welcome to Fight Club.