Some jobs reveal corners of life most people never see. On Manhattan’s Upper East Side, behind tall doors and private elevators, a parallel world exists where nannies manage the daily lives of children whose parents collect cars and art as if it were routine. The work pays far more than many expect, but it also demands tasks and sacrifices that would be unacceptable in many traditional workplaces. Stephanie Kiser knows this world intimately.
A Career by Chance
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Like many young adults, Stephanie moved to New York City after college with dreams—she wanted to write for film and television. Reality, however, arrived sooner than opportunity: rent in Manhattan doesn’t wait for a breakthrough. Nannying started as a temporary solution but soon became a full profession.
Her first position paid roughly $20 an hour, already better than many entry-level production jobs. That experience led to placements through agencies and, with each move, increased responsibility and a larger salary. By her final year as a nanny, she was making about $110,000 and often working 55 to 75 hours per week.
Front-Row Seat to Privilege
Stephanie’s daily life took place in homes that resembled private resorts. Luxury cars idled in driveways. Some households employed a full on-site staff—a chef, a sous chef, a butler, and rotating housekeepers whose job was to launder and press clothing all day. She escorted children to tutors charging $500 per session and handled logistics for day camps that cost $13,000.
In closets she found rows of Oscar de la Renta dresses in toddler sizes, some costing more than $400 apiece. The children wore these clothes to school, where classmates’ parents included actors, investors, and CEOs.
The Reality Behind Six-Figure Pay
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In wealthy households, nannies typically work without the protections of a formal HR department, so contracts are crucial; families define the terms. Hours, duties, and expectations can shift with little notice. Some employers provide health benefits and paid holidays, but others pay cash and expect near-constant availability.
Stephanie often found herself performing tasks far beyond childcare. She hand-washed delicate underwear because it was too expensive to discard, cleaned individual Lego pieces, and meticulously tracked ointment jars so they always appeared untouched. On one weekend she was summoned to the Hamptons to look after a billionaire’s young son; when the family moved to their yacht, staff drove ahead in golf carts and instructed her to run behind them down a long path to the dock. At another job she watched a child deliberately soil himself as an act of defiance.
Class Shapes the Smallest Details
Working in those homes made Stephanie acutely aware of the gulf between her upbringing and the childhoods she tended. She grew up in Rhode Island in a family that struggled—groceries were stretched, bills were a regular stress, and debt collectors sometimes called. The children she cared for attended schools with gallery-like lobbies, spent afternoons in manicured parks, and snacked on gourmet food brought by household staff.
Those contrasts underscored how much early advantage—access to tutors, enrichment, and networks—can shape a child’s future. The job also exposed how race, age, and appearance influenced treatment within the field: agencies often favored young, white, college-educated nannies and offered them higher pay than older or immigrant nannies, even when those women had more experience. In some households, parents would address Stephanie while ignoring other nannies entirely. A friend once told her about a barbecue where the family refused to allow nannies to eat the same steaks served to guests.
Leaving the Work Behind
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For Stephanie, nannying became more than a job; it created deep emotional bonds. Leaving an employer often felt like saying goodbye to family. She remembers lying sick in bed after her final day with one household and missing the children almost immediately. Those relationships softened the job’s harder aspects, but over time she wanted a career with clearer advancement and stability.
She transitioned into roles as a personal assistant and later rose to a senior executive assistant position at an ad-tech company. Her salary took time to reach the level she had achieved as a nanny, but the new role offered health benefits, a predictable schedule, and a more defined path for professional growth—advantages nannying rarely provides.
An Honest Look at a Hidden World
Stephanie’s memoir, Wanted: Toddler’s Personal Assistant, recounts those years with a blend of humor and realism. Her stories range from indulgent moments—gourmet sandwiches and chauffeur rides—to surreal episodes, like sprinting after a golf cart on a billionaire’s estate. More importantly, the book reveals social dynamics often hidden in plain sight: the unequal treatment of nannies based on race and education, the unspoken rules that govern wealthy households, and the relentless pressure to meet expectations that can never be fully satisfied.
Her account offers a candid portrait of a profession that sits at the intersection of intimacy and labor, revealing how care work can be both personally rewarding and institutionally precarious—especially when performed within the insulated worlds of extreme wealth.