Beautiful Virgin Islands


I’m a 23-year-old nanny for a wealthy family in Nantucket. I get to fly on private jets and document my daily adventures on TikTok.

I’m a 23-year-old nanny for a wealthy family in Nantucket. I get to fly on private jets and document my daily adventures on TikTok.

Evellyn Singleton landed a full-time nannying gig on Care.com. After posting about the boy she watches, brands started reaching out for partnerships.

Baptism by fire is the best way to describe my early days as a full-time nanny.

When I received a message on Care.com last September from the woman who would become my employer, I had never met her, her husband, or Jacob, the adorable toddler I'd grow to love.

Jacob's mom told me she was initially drawn to my profile because it really focused on who I was as a person rather than just listing my nanny experience. When you invite someone into your home who's going to care for your child, you want it to be the type of person you can trust to serve as a role model, so it was important for me to go beyond simply listing my previous work experience and share my interests and passions.

After we connected on the website, we set up an hour-long phone call. It was clear the family was looking for someone willing to play an active role in the boy's life and not just "watch him." I was asked what developmental activities I would plan and how I would track his developmental milestones. That initial call was followed by a FaceTime session, which led to a job offer.

The family was living in Nantucket, Massachusetts, for the month, but they're based in Nashville during the rest of the year. After I'd graduated from the University of South Carolina in 2021, I'd moved to Nashville for a sales job at a Fortune 50 company and learned I wasn't cut out for corporate life — at least not the role I was in — so I resigned after six months.


I'd nannied during my summers, but this was my first live-in position, and it would be on an island I'd never even set foot on


But since I had nothing keeping me in Nashville, I jumped on the nanny position when it was offered to me.

Per our arrangement, I would care for Jacob on weekdays from 9 a.m. to 5 p.m. with an additional five hours of flex time per week to be used for things like date nights.

My duties would include caring for him, cooking for him, and doing his laundry, and I was to be paid by the hour with time-and-a-half for overtime.

I was excited about the opportunity but also nervous. Despite my poking around the internet to learn more about the family, they were strangers, and I wasn't certain we would mesh. In the end, I figured if things didn't go well, I could always resign, get on a plane, and return to Nashville.


Two weeks after receiving the offer, I flew to Nantucket, met Jacob's mom at the airport, and drove to their vacation home


I was given my own bedroom outfitted with a queen-size bed, a full bath, and my own walk-in closet. In addition to that, all of my grocery and personal-care items were taken care of.

Jacob's parents have always had a "What's ours is yours" attitude, granting me access to their cars and bicycles and even extending an open invitation to join them for meals and activities on my days off. There's never any pressure to join them, but I often do because we genuinely get along with each other and enjoy one another's company.

When we first got to Nantucket, it was just me, Jacob, and his mom. Jacob's dad was still wrapping up work in Dallas, where they lived prior to moving to Nashville. Each night after Jacob went to bed, his mom and I would sit down and watch TV together. We bonded over episodes of "The Bachelor" and "The Bachelorette" series.


When you live under the same roof as your employers, there's the constant challenge of balancing the personal and the professional 
Singleton and Jacob in Park City, Utah.


We've been very fortunate to have gotten along since the start. Knowing your worth and sharing a mutual respect for one another is a key part of making things work. Another key element to ensuring a smooth working relationship is maintaining a strict set schedule, something Jacob's mom and I are both fond of, especially in a live-in situation.

Jacob is a good sleeper and often sleeps 12 hours a night, waking around 7 a.m. Although I don't officially start work until 9 a.m., I normally have breakfast with him and his family around 8 a.m.

Jacob's mom gives me complete freedom in terms of how Jacob and I spend our time, and I keep an extensive list in the notes app on my phone of fun activities we can do.


Every day, we do one activity before lunch and another in the afternoon after his nap


Sometimes we head to the beach or go to a local driving range and hit golf balls, while other days we might visit an animal shelter and play with the dogs there or go to a museum.

Flying is definitely part of the job, as Jacob's family enjoys travel. On several occasions, we've flown private planes and jets chartered for the day. One of my favorite memories was when we chartered a plane to fly us from West Palm Beach to Key West for lunch and then returned back in time for dinner at The Breakers, a luxury resort.

Singleton on a chartered flight with the family.


In Nantucket, on weekends when I was off, some days I'd head to the beach, take the car and go shopping, or meet up with new friends I made from social media.


One rainy day while sitting around the house with the family, Jacob's dad suggested I post about my adventures with Jacob on social media


He joked that Jacob was such a cute baby, we should make him famous. I also think Jacob's dad sensed I was yearning for something to do in addition to nannying and needed to find another outlet for my energy. His idea hooked me immediately.

I love social media, and I'd already made a habit of regularly documenting our time together and sending photos to Jacob's parents, so posting content online was a natural extension of that.


I suggested creating TikTok videos set to music


We laid the groundwork in terms of what was off-limits, like addresses, certain names, license plates, or anything related to Jacob's dad or his career. Before I post anything, I always send them a draft to ensure they're comfortable with the content. There's never been an issue.

My posts have garnered more than 82,000 likes on TikTok, and I recently created an Instagram account for Jacob that I run as well.

Since I started posting videos of us, I've had people roll down their car window when they passed us by on the road in Nantucket and say, "Hey, aren't you the nanny on TikTok?" which always blows my mind. We've also had kids brands reach out about doing potential partnerships. Right now, we're in the early stages of partnering with a STEM activity brand for children on TikTok, which is exciting.

We're still hammering out the details, but a percentage of any profits earned from endorsements will be set aside for a nest egg for Jacob's future. I'll receive a percentage, too. Maybe Jacob will want to explore his own business venture one day and will be able to use this reserve to do it.


As for my own future, it was never my intention to be a career nanny


I watch Jacob in Nashville now that we've returned from Nantucket, but since he's started preschool, I've decided to transition to caring for him part-time so I can begin putting my feelers out for my next opportunity.

Jacob is also going to become a big brother soon, and we're ready and waiting for his sibling's arrival. I've already created a second Instagram account for the baby.

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