Chapter 4: Being an ‘assistant’
The Devil Wears Prada tried to warn me…
One of my absolute favorite movies is the Devil Wear’s Prada. When I was younger (read as before I worked beyond my high school days of making money to go to the mall) it inspired me to want to work for someone like Miranda Priestly.
I could take her.
I really, really could. Bring it on.
How hard could it honestly be to think for someone else before they know you need to think for them?! How hard could it be?
Well, younger me, it’s actually really hard, and how naive of you to think differently.
My first indication of this wasn’t actually a personal experience but took place on my first visit to NYC when I was a senior in college. My best friend was exploring going to grad school on the east coast and, in case you forgot, I was supposed to be going to law school. So we used the same excuse of needing to “visit schools” as a reason to explore NYC (neither of us was going nor applying to a school in NYC but you don’t go to the east coast and just overlook a chance to experience NYC for the first time). So in between extremely important campus visits in Cambridge, Mass, and wherever Yale is, we decided we could go “see Columbia” but honestly, we just wanted to see if NYC was anything like the TV shows.
It isn’t. Spoiler alert. I wouldn’t really get that for a few years though and that’s an entirely different book but let me just say my first apartment was a 1 bedroom and there were 3 of us…our only privacy was a curtain. Just let that marinate for a bit.
I digress.
But, on a random day in NYC, while we were exploring, we stopped in a Starbucks for the 10th time that day somewhere in the general vicinity of Times Square. While waiting for our coffee with a few 100 other people we encountered the first real-life Miranda Priestly moment. Some poor soul was having a true breakdown because the barista had done regular foam instead of a light foam. My friend and I laughed because how can you honestly tell the difference? However, the emotional response this individual had and the amount they begged for the barista to not just remove some of the foam but to make an entirely different drink because their boss would notice regardless, just didn’t seem real. When I say they were having a breakdown, I’m not exaggerating. There were tears and the willingness to pay double for the new drink. Even the barista looked shocked but took pity on the poor soul and remade the drink. We then witnessed said individual sprinting back to wherever their boss was; probably nervous because they were now late due to the incorrectly made drink. I wonder what happened to that individual…
A few years later, I’d fully understand how real that moment was because I worked for one of those people. My first boss was known as a “dragon” and he was. One of the first things he ever told me was that I was
“his eyes and ears; I needed to think like him and know what he needed before he did”
Sure, fine, but also keep in mind that I was his virtual assistant. I never, even to this day, have met him in person. Our entire relationship was through written communication and the occasional call when he felt he had “time”. Now, don’t get me wrong, it wasn’t the worst-designed role but his expectation for me to just know him when I never met him was a bit absurd.
And here’s the thing — even the world’s best assistants aren’t psychic. Crazy, I know. But they aren’t. And the individuals they work for set unrealistic expectations if they think they should be. Here are some red flags for jobs calling for assistants and situations you should consider your sign to run if you find yourself living them:
🚩 No one is available 24/7 — that isn’t a reality you can maintain so don’t say you are. Being available when needed, during hours that make sense, you can do and agree to, but getting yelled at because you didn’t answer a text at 3AM? No. And trust me, if you say you’re available you will get a 3AM.
🚩 Going through more than 1 assistant a year isn’t normal — you should ask how many they’ve had before accepting a job. If someone has had a rotating door for assistants (I don’t care how famous) this is an issue. It’s actually not that normal to have 1 per year but anything more is cause for concern. I recommend running.
🚩 If the team gets nervous when they’re around, problem. One of my favorite moments in the Devil Wears Prada is the scene of everyone panicking because Miranda is early. They all throw out their carb-focused food, put on what look to be the most uncomfortable shoes, and some even change their clothes. This isn’t normal though. Impressing your boss is one thing, but fearing their mere presence? Not good. Good TV does not equal a good reality. I used to literally dread my boss’s name showing up on my phone. Red flag. The team also used to hate when he did show up to the HQ in LA and would make up every excuse to not go to work that day. More. Red. Flags.
🚩 Your life doesn’t stop to be their assistant. Sure you may travel more and you may have a hard time squeezing in two week holidays but your life doesn’t become theirs and they shouldn’t want that. If you are spending countless hours with one person and they’ve never bothered to ask you about your life, you’re working for someone who has zero awareness of others. You still matter even if you spend most of your time caring and thinking about them.
🚩 Respect goes both ways. I’m not sure who told individuals that their employees have to earn their respect only but it is a two-way street. You may be proving yourself as the right person for the job but they also need to prove that they respect and appreciate all you do for them.
🚩 Their fame or wealth doesn’t replace their humanity. They are humans. They are not above the law or above you. Remember that. I once witnessed a celebrity (we’ll keep them unnamed here…)fire their assistant by yelling at them over the phone in front of 60 people because they didn’t predict their boss waking up that morning and wanting to take a Soulcycle class. I don’t care who you are or what millions you make, there is no excuse for this kind of treatment to your employee who, fun fact, didn’t book the bike because their boss was supposed to be on a flight to NYC that he missed and didn’t bother to tell anyone he wasn’t going on. Again, assistants aren’t psychics.
🚩 You are not responsible for their mistakes. I’ll say it again for the people in the back, you are NOT responsible for their mistakes. If they sleep through an alarm? Not your fault. If they say yes to an event and double book themselves? Not your fault even if you have to clean it up. If they get in a fight with their partner or spouse? Not your fault. If they don’t get a job or book a show? Not your fault. If their agent or manager hates their work? Definitely not your fault. They are responsible for their work and their actions, not you.
🚩 Their power, influence, or money doesn’t eliminate the need for boundaries. Again, they do not own you because you work for them.
There are some great opportunities when it comes to being someone’s assistant in an industry that you want to have a foot in the door to. Music, TV, fashion, etc. are industries that are about who you know and who has known you, so being an assistant to someone with that kind of influence can be hugely beneficial to your career, but these roles have also proven to be some of the more emotionally damaging ones as well. You have to have a thick skin but also know your worth — your self-respect and advocating for yourself will make these jobs both bearable and sets boundaries with the person you work for if they chose to show you equal respect.
You may be working for them but you are representing you. Don’t stay in a situation that you dread or find yourself going home in tears daily because it won’t be worth it if you fear showing up every day.
I lucked out in the fact that I got to work with people who I was able to vent to about our said “dragon” and, again, I never actually met the dragon boss in person. But it took one day about 4 months into my time working for him where I explicitly told him that yelling at me was disrespectful and would no longer be tolerated for our relationship to start to become a two-way street. A bumpy street mind you but never again did he call to scream at me for a mistake he, himself made. I set the boundary.
Remember, you are always in control. Your “dream job” isn’t a dream if it feels more like a nightmare.
