If you have a lot of money, the gifting stakes are high — but chances are you’re paying someone else to do the grunt work for you. “The holidays are notoriously hell for personal assistants — they’re basically running Santa’s workshop on top of their normal job,” says one former PA. “People used to refer to my desk as the North Pole, but it really wasn’t funny.” Here, three personal assistants (both current and former) recall the spreadsheets, hyperspecific wrapping paper, and over-the-top requests they’d manage during the holiday season.
“I almost mixed up a gift once, and I legitimately thought I would lose my job.”
—a former executive assistant in New York
I was one of two assistants to an executive in the fashion industry, and we were in charge of maintaining a spreadsheet of all the people that our boss wanted to send gifts to during the Christmas holidays. It was an all-year-round project. My boss constantly received gifts from fashion houses, book publishers, and so on. Most of it was designer bags, designer scarves, Chanel, Hermès, Celine. So many candles. She got so much stuff that it was impossible for her to keep it all for herself. So whenever she received a gift that she thought was appropriate for someone else, she would tell us. Then we’d note it, tag it, and store it in a special locked closet until the holidays.
Around November or December, we’d carve out an area of the office as the gift-organizing station. We would then wrap and deliver the gifts, either posting them overseas or using the company’s messenger service. The night before our office shut down for the holidays, the other assistant and I would go around the city in a limo that was reserved by the company, delivering the final gifts.
Our boss never used company funds to buy personal gifts. But sometimes she would have one of us reach out to a PR person to request an item that she wanted to give to someone, either at a discount or for free. I know it sounds ridiculous, but it was a very common thing for high-ranking executives in our industry to get these kinds of perks. She was also a really thoughtful gift-giver. She chose things very carefully and really wanted them to be meaningful.
I don’t think any recipients minded that things were regifted, and there wasn’t an effort to cover it up. They were amazing gifts! If you get an Hermès scarf, do you care about how it was obtained?
I almost mixed up a gift once, and I legitimately thought I would lose my job. I put someone’s name on a candle, who I thought was the right recipient. And my boss came over and was like, “That’s not the right candle. Where is it?” And I was panicking, trying to remember which candle she had chosen months ago for this person. I spent over an hour digging through the office to find it. Eventually it was located, and I was incredibly relieved.
The whole operation was absurd, and there were times that I resented staying at work late to tend to my boss’s personal matters. But the upside was that she’d give things to us, too. There were these fairy-godmother moments when she would tell me and her other assistant to go into the gift closet and pick something for ourselves. I was making $40,000 a year at the time, and I would never, ever be able to afford a Gucci bag, which she did give to me. Even now, years later, I probably never need to buy another bag in my life. I have some beautiful bracelets and earrings. I’ve definitely sold some of this stuff on the Real Real, even though I wasn’t supposed to.
At the end of the year, any gifts that didn’t get sent to her friends, family, or industry contacts were put out on a table and the rest of the company staff would get to take things for themselves, too. People would line up and, one by one, pick an item of their choice. There was a huge variety. You might wind up with a junky piece of jewelry, or you could get something amazing.
“They have referred to me as an elf.”
— owner of a personal-assistance service in New York
I run a business that provides part-time personal assistance to multiple clients, anywhere between ten to 20 people at a time. My clients’ needs vary a lot. Most of them have full-time staff in addition to us, so we’re here to help with extra things they want. Right now, that’s a lot of holiday stuff. I’m actively managing gifts for about half a dozen clients.
Some clients know what they want, and we’re just there to purchase, wrap, and deliver it. Others want us to give them ideas for their mother-in-law, their kids, their staff. So we’ll put together a list and show them. I usually start looking for gift ideas as soon as the summer’s over.
I have one client who, every year, has me ship their gifts to my own home so that we can wrap everything and deliver it to their home on Christmas Eve, like Santa. They have referred to me as an elf. I live in a New York City apartment, so I keep all the boxes piled up in a corner. Then I will have one or two people who work for me come over, and we will wrap everything and take it to their building.
When it comes to wrapping, everyone has a specific look they want. One client is historically very traditional, so I can almost anticipate what they will ask for. But then I have another client who is much more specific aesthetically. This year, they sent me a reference picture of some gifts and wanted to emulate the style of how they all looked together, almost like a mood board. And so we sourced a bunch of wrap and ribbon and other items to try to get the same vibe. Style is very important to them.
Another client wants us to use two different gift wraps. One is meant to be from Santa, and the other is meant to be from family with tags that say it’s from Grandma and Grandpa, or Mom or Dad. And the Santa ones don’t have a tag; they’re just wrapped differently.
Most of our clients have multiple homes, so sometimes we’re storing gifts at one home until they decide where they’re going to spend Christmas, and then we’re making sure the gifts get shipped to the right place on time. They usually do fly private, though, so sometimes everything can fit on the plane. I always say, as long as it’s legal, we’ll do it. I’ve had a lot of my clients for over ten years, and luckily most of them are past the point of asking for stupid stuff. Some people used to ask me to get drugs for them and things like that, but that doesn’t happen anymore.
I’ve noticed that how people obtain their wealth seems to affect how they give gifts. For example, someone who grew up upper-middle class and then made a bunch of money through their business, they might have a roomful of gifts. It’s more dramatic. Whereas people who have generational wealth typically won’t be as flashy. They give to the same people every year, and they’re generous, but the gifts won’t be endless. They’re more chill.
“A very important gifting rule is no food. People are always paranoid about getting poisoned.”
— Brian Daniel, personal-assistant recruiter based in L.A.
I once had a client who wanted to give gold coins as gifts. I was in charge of making a list of all the people who would receive them. Then I had to divide up the coins among those people. Then the problem became, How do you present these coins? You can’t just have a little baggie, like a Ziploc or something. They had to go in something. I wound up finding a glassmaker to make these little glass boxes to put the gold coins in. They were like glass treasure boxes — you could see through it, and see the coins inside, which was really dramatic.
During the holidays, I’m constantly getting emails from people who need additional staffing support. Gifting season is nuts. The VIP clients can spend a lot of money on gifts, and the people they’re shopping for obviously have their own money, too. So it comes down to finding special, unique gifts that blow people out of the water, stuff that’s hard to get.
The billionaires and celebrities in Hollywood are always working behind the scenes to maintain relationships and keep the wheels greased. It’s a lot harder than most people think, honestly. Someone will be in a hit movie and maybe one or two others and then they disappear. It’s because they’re not schmoozing and trading favors and making connections. These are niche ecosystems, and the relationships are very fragile. You have to constantly work at them to stay top of mind. Gifts are part of that.
Anybody can buy and wrap a gift. But to wow someone, you have to get something one-of-a-kind and special. There was this store at the Beverly Center that had a rare-documents collection, like stuff signed by Abraham Lincoln, that was very popular. I had clients who would get all their holiday cards hand-written by a calligrapher. I was recently at Tiffany’s in Riyadh, and they had this tiny platinum race car. It’s Tiffany blue with diamond accents. And I thought, “That’s a great gift for a billionaire’s kid.” It’s definitely something that, if I still had a certain type of client, I would present to them. I used to make whole presentations with gift options before the holidays.
Even the wrapping paper is important. I had a client once who used gold-leaf wrapping paper. Another time we were wrapping gifts with sheets of money, uncut, that supposedly came from the treasury. We had these huge sheets of currency, hundred-dollar bills. I have no idea how they got them, or if that’s even legal.
Another issue is delivery. A lot of these VIPs have many layers of security, so you can’t just drop something off, especially when the gift is really valuable — you want it handed to the person. It’s very difficult, and you have to know who to call. The PA has to navigate their way in and make sure it gets to the right place.
A very important rule is no food gifts. People are always paranoid about getting poisoned. In the entertainment business, there are a lot of wackos trying to get at people, and so everyone has security training and an abundance of caution. Even if it’s a cake from a famous chef, they won’t accept it, and it’s considered rude.
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