What It's Like to Be a Celebrity Nanny

baby bottle and bedazzled pacifier
Photo Illustration by Aly Lim
Getty | Tooga; Turnervisual; Nenov
Photo Illustration by Aly Lim
Getty | Tooga; Turnervisual; Nenov

There's a secret game of "Where's Waldo?" going on among celebrities. Sometimes it's spotting a hand, other times, part of a uniform. But any time anyone catches a glimpse of camera-shy Connie Simpson — better known as Nanny Connie — in a photo, she immediately starts getting texts from her former families.

For nearly four decades and over 300 clients, the caretaker from Mobile, AL, has become one of the most in-demand nannies floating between famous families. Clients include Jessica Biel and Justin Timberlake, Emily Blunt and John Krasinski, Amal and George Clooney, Matt Damon and Luciana Barroso, and Jessica Alba and Cash Warren.

Simpson, who wrote the 2018 book "The Nanny Connie Way: Secrets to Mastering the First Four Months of Parenting," helped watch her cousins as a teenager and went on to study early childhood education before nannying for families around the globe.

"Babysitters have that inner calling to want to be more, but if it's your passion, you tend to never be able to get away from it. That was me," she tells PS from Maui, where she's currently working. "It was something I loved doing, and 40 years later, it's like, wow, I've been doing this a long time."

It was Simpson's southern upbringing that helped ingrain the most essential lessons of family dynamics in her. "Back then, you put your family first — the generational home was truly important in the '60s and '70s," she says. "That's where I've gotten all of my know-how from."

In our high-tech, fast-paced lives these days, so much of that family fabric has unraveled. "But it's so needed," Simpson says. "It's a thirst we need to quench, and we don't even know how to because we've lost the blueprint."

Simpson enters famous homes with this homegrown perspective, and leaves as part of the family. Below, she speaks to PS about her experiences nannying children to the stars.

PS: How do you build a solid foundation when you first start working with a new family?
Connie Simpson: Talking with both of the parents is truly important. I like to connect, especially with eye contact, and by telling the parents, "Congratulations on getting to this point. This is your most prized possession." That levels the playing field between husband and wife or partners. I'm there to help give them the tools they need and the empathy that's going to help them show up better. There is no book, so to give them the first three pages of the first chapter is golden. It's like winning the lottery.

PS: How did you start working with high-profile clients?
CS: It's never been intimidating for me. I've worked in the one-percent world all my life. My parents were both in the service industry — my father was a postman, my mother was a nurse. The way I was raised, you don't see a person in particular, you see a human being. I can disarm a person as powerful as [billionaire businessman] T. Boone Pickens to, say, talk about home cooking. When you get on that same playing field, now you've made them human.

I've been in many homes of great writers and phenomenal scientists, and they never let me know who they were. They just wanted to seek information from me, and then I come to find out they had a "PhD" after their last name, but I didn't know that. I was being tested. That built my confidence to know that I can hang with people from Harvard, Yale, and Columbia University, and they'll be educated by me just as much as me being educated by them.

PS: How much time do you typically spend with a client?
CS: I check in a day, sometimes two, before the baby gets there. I stay 24/7 — I do not leave your home. When I'm in your home, I'm there to observe what's happening, see where I can help, and see how I can help you show up better. Then I leave six months, a year, or five years later. There have been some who have kept me because they wanted to make sure I was there for the next one. It's been an amazing journey.

PS: What is a typical day like in the life of a celebrity nanny?
CS: My goal is to intertwine real life with their glitzy world. I want to know their schedule, so I can help them show up in their schedule for their child. If they're going to be on a shoot, I'll say, "OK, you've got to leave here at 8:00. Do you want to do the morning feed or do you want us to come to the shoot?" I'll make the arrangements to show up, so that the parent can be with the child.

"My goal is to intertwine real life with their glitzy world."

I don't want them ever to feel disconnected from the parenting world, and I do that in such a loving and smooth way. I'm not trying to pat myself on the back, but they feel so comforted because their jobs are so demanding and parenting is so demanding.

PS: What are some of the ways you bridge that disconnect?
CS: I get up early in the morning with them. I'll send pictures throughout the day, and I'll go, "Hey mom, I was thinking about you. I spit up all over Nanny, but I can't wait to get home so we can have time together." That does amazing things to the ego of that mother who had to go for a 4 a.m. shoot and won't get home until 7 p.m. Those are the little driblets that you do to make a mother feel like, "I did the right thing. I am going to be OK on my journey as a parent and in my profession."

I also get working dads to support the feelings of the mother because a lot of times, they don't talk. But I see it, so I help them. I'll say, "I want you guys to go out to dinner this Thursday night. There's no talking about the baby." They come back and go, "Nanny, I did realize how important that was, and we talked about you more than we talked about anything."

PS: Are there added stresses with celebrity clients?
CS: There is a lot of added pressure with the paparazzi and the surrounding people taking pictures. They want to see more failures from them than successes. So we practice before we take the kids out. I give them an at-home tutorial. I am a pitbull in a way because I will strategically place myself, so that mom doesn't feel awkward when she takes the baby out of the stroller. If we go out to lunch, I will have us sit at a certain table, so I can block the view.

It's important for them to practice being out. I don't feel like I've successfully done my job until I've touched all of their bases in their life: going to the supermarket, how to take the car seat out, how to do the stroller, mom and dad being together in the car, the window being up, the wearing of the little harness, all of those things. Those are important.

PS: The lifestyles of these celebrity kids must be so different. How do you handle that?
CS: I treat them just like everyday children. They don't know no different. They get the same Nanny Connie as their parents: With Justin [Timberlake], I was like, "Son, don't ask me none of your music, because I know none of it." When I started with Matt [Damon], everybody in my family was like, "Wow, you're going to work for Jason Bourne." I was like, "Yeah, but I ain't watched none of that!" But you want to ask me about "The Talented Mr. Ripley?" He blew the doors off of that one. That was a hell of a movie.

You would not believe how many people just want to be respected on that everyday level. For the children, I give them the same. I'll tell them, "You keep it up. You're gonna come to my hometown in Mobile, and we're gonna end up doing yard work." I make the older kids do stuff around the house and fold clothes. I keep them normal. The parents want them to have that normal life — they don't want their life to be a curse to them.

PS: Jessica Biel called you part of the Timberlake family. How does that level of bonding form?
CS: There are really intimate moments that happen. I'll cook for them because I want them to have a home-cooked meal. I don't want it to come from Uber Eats or something. I've done Thanksgiving dinners with them, and I'll say the blessing. In our family, we say, "Rise Peter," and the family's response is, "Slay and eat." That's from the Bible. A lot of parents would love to have that uniqueness come into their home, but they don't know how to because they're so caught up in the tinsel world.

I hover, but I don't push. I give love and consistency. I can see the need for humanity to have more empathy, and I think that's what's made my connection with so many of them.

PS: John Krasinki in particular said you've changed his life. How does that make you feel knowing you've been so instrumental?
CS: I feel that we all have a calling in life. Parenting is the closest thing you can get to the heavens. To help a parent find their wings and their footing, gives me great joy. It gives me great joy.

When John comes to me, or Matt comes to me, or George [Clooney] comes to me, or Justin comes to me, and they put their arms around me and tell me how much I've impacted their life, I'm so honored. That is a part of my heart that I left with you, that gave you more than any of what you could have gotten in your industry.

PS: What do you wish parents would ask more?
CS: They do ask me so many questions. I'm very intrigued that so many fathers, even second time fathers, are asking me those questions about skin-to-skin contact. I'll show them because children's first language, their love language, is this sense of touch. When you touch a baby, they're getting a reading from you, like a pulse oximeter. They're getting how calm you are. They're getting your anxiety. They're getting all of that. Now you're setting the pace for them.

Skin-to-skin is not just trending parenting — it's a journey. It's letting them hear your heartbeat when they're upset, so they learn to regulate themselves, and that helps with their anxiety. That helps with sleep training. Skin-to-skin is the absolute first in teaching your children how to navigate their emotions and their feelings.

PS: What's the one tip you'd give to a new parent?
CS: There are going to be mistakes. As you're preparing for a baby, you're trying to make everything perfect, but there's so much imperfection in parenting. I'm not going to say, "give yourself grace," because that's bullshit. That's just a pretty way of saying it. I want you to be mindful that there are landmines out there that are going to blow you out the water every day. And if you make it through a day and you don't get blown out the water, count your blessings. You're doing it right.

Rachel Chang is a travel and pop culture journalist and a magazine editor (Us Weekly senior editor, J-14 editor in chief, CosmoGIRL! entertainment editor) turned freelance writer. She's a regular contributor to Condé Nast Traveler and Travel + Leisure, and has written for PS, New York Times for Kids, Wall Street Journal, Lonely Planet, and United's Hemispheres, among others.