An Inside Look At Being A Personal Assistant For The Rich & Famous



Personal_Assistant_to_the_RichPhoto: Rex USA.
The Billfold — which, mind you, is not another personal finance site — aims to do away with the misbelief that talking about difficult money issues is uncomfortable. Instead, they've created a space to have an honest conversation about how we save, spend and repay our debts. Or, why we'll buy a dozen oysters before we pay our rent.

How many times have you wished for a personal assistant? Someone to pay the bills, schedule the doctor visits, put gas in the car? You can’t talk to Amy Cray without wishing she would come to your house and make everything easier. She’s just that kind of person — with an easy smile and a competent, friendly manner.

She’s also the personal assistant for, among other clients, a Very Famous Literary Personage. Personal assistants of Amy’s experience make $80-$125K annually, plus health, retirement, and bonuses, but those positions are hard to come by. Amy is in the middle of that range. Personal assistants with moderate experience working for CEOs, CFOs, etc. generally make around $60K.

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Amy grew up in the mountains of California, in a town of 80, with parents that were, as she puts it, “not pop culture hippies, but real ones.” She left at 18 and moved around the west coast, nannying and cooking to pay the bills and support her music career. That gradually turned into jobs running the households of people with, as she said, “tons of money.” Now 38, she lives in the Bay Area with her wife and two young children, and has a blog.

I was curious about what it was like living with the rich without being one of them. Here’s the edited version of our conversation.

How does it feel working for people who have so much more money than you do?
"It’s so crazy. It’s really interesting. So my wife: The majority of her career has been in nonprofit and she does work to support homeless and low-income families. So, we always say we actually do the same thing. But she does it for people with no money. And no house."

Who gets paid more, you or your wife?
"Oh, me. And that’s sort of a family choice, to split the difference.

I’ve worked for globalizers before and felt like was I was helping make the world a worse place, and kind of felt that guilt. This is a personal thing — I don’t find this a lot with PAs — but I need to know that the life that I’m supporting is doing something good for the world. If I’m spending time away from my kids and away from whatever other priorities I might have, and working really hard, I need to know I’m doing it for somebody who deserves it.

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Then again, a lot of it is frivolous and superfluous, and “Oh, can you book the tickets to Dubai?” So, we’ve always felt that it’s a comfortable equality for our family if she’s like, working to “save the people.” It evens out a little bit."
Personal_Assistant_to_the_Rich_3Photographed by Rockie Nolan.
Is it weird dealing with such big sums of money like you do?
"I carry my clients’ credit cards with me because I purchase on their behalf all the time, so for me it’s just completely normal to be like “charge that $6,000″ and not even think about it. And, it is very strange because it does seep into your life — your normal life. Like, I’ll write people’s tax checks for $400,000 and just the act of writing “400,000″ on a check — having had that experience! Even if it’s not your money.

There’s a little bit of ownership that sort of seeps in. That creeps me out every once in a while. Like the bonuses. We’ll talk about holiday bonuses. “How much did we give the housekeeper last year?” And that’s a normal thing for me to say. And then later I’ll be like, oh my god, that’s crazy. Part of that is just because it’s such intimate work. It is your life, in a way.

But yeah, the spending thing is strange. I see that being confusing, actually, more for my family than for me. Because I sort of come home with those experiences: Like, oh, I just packed so-and-so off to Paris for Christmas. Like a client bought a $90,000 car one day just for his wife, for fun, just “Happy Thursday!” And me coming home and saying, “I took the new BMW out for a spin. It was super fun”—my family is kind of like, “What is this life that you live?”

And for my daughter especially cause she’s like, “Well those kids all have iPads, and why did they get to go to London over spring break and we went to nana’s house?”"

What do you tell her?
"She’s never said anything to indicate that she feels she deserves that too. I think she does get the concept that these kids live a different life than what we live, and they have the kind of money that they can just do stuff like that all the time. She also knows that they aren’t any happier than we are."Because you spend large sums of money, even if they’re not on your own behalf, do you get that special kind of treatment? That different way the rich are treated?
"You sort of have access to that world. That’s actually very true. I also do know what kind of power that wields, whether it be name-dropping or access to money or knowing that we could make things difficult for a vendor, if they really screwed us over. People would listen."

Do you ever get jealous, not so much of the money but of that ability to get things done?
"I feel like my clients are usually about 20 percent less happy than anyone I know in my income bracket.

The perk of being able to throw money at something — that’s amazing. I love that. You problem solve by throwing money at it. And that’s the kind of thing that I’m like, “Ah, that’s so awesome, you just take the credit card and make his problem go away.” But, I’m never jealous of it because I feel like ultimately that doesn’t outweigh the benefit of having either more time with the people who really love you, or access to people who you know love you for you, not because you’re famous."
Personal_Assistant_to_the_Rich_2Photo: Rex USA.
As a musician yourself, do you like working for other artists or does it make you wish you could make money off your own art instead of being a PA?
"That’s a funny question because what I’ve learned is how hard it is for almost anyone to make a living off of it. It doesn’t make me feel better or worse. But people in the fringes of my Bay Area family will mention, 'I want to write a book' and I’ll be like, 'Oh no, no, no, god, no, don’t. You don’t want to get into that.' Because I see how hard it is. It’s impossible. It’s hard for people who are really good at it and do it very well. In my current position I know so many writers in various stages in their careers and varying degrees of talent, as well as people who are world-class, phenomenally incredible writers — we’ll have coffee with them, and they’re around. It’s hard for those guys! You don’t really ever know when you’re next paycheck is coming."

Even when you’re at the top of the heap?
"It’s still super-stressful. Specifically for writers."

What makes a good personal assistant?
"Loyalty is huge. You cannot have someone in this position — in positions like the ones I have nowadays — who doesn’t come with incredible recommendations, because you’re placing them in control of everything. They know more about your investments than you do, they are managing the other people that help you, whether you have nannies or people working on your house or people who are interacting with you in your work life, and running your career. If you have a point person like that, it has to be someone who’s been doing it a long time."

So this kind of job — is it salaried?
"The good jobs are salary. The part-time jobs and the ones where you’re not an integral part of daily operations are hourly. The holy grail is a salaried job with a 401(k). It’s like a whole corporate structure. That’s the thing that PAs, professional PAs, go for. Usually there’s travel, sometimes there’s housing provided."

Are you where you want to be in your career? Is being a PA the job you want to do forever?
"I’m kind of at the point where I could stay at the level I’m working at now. I could pretty much work for anybody, except for billionaires. There’s a huge jump between the two. There’s this kind of money and there’s that kind of money. But that’s really distinctly separate by what kind of network we’re talking about. People who are billionaires — they have a staff of MBAs working on their team and you could be one of those people. And, I could do that. I don’t know that I want to, because it’s managerial. It’s not as personalized.

Right now I feel like I’m absolutely doing the thing that I should be doing. Whether or not I feel like that in six years, we’ll see."

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