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While Young Graduates Face Salaries of US$ 65 Thousand, Burnout and Mass Layoffs in Offices, Nannies, Drivers and Private Chefs Fly in Private Jets, Live in Guesthouses and Accumulate Benefits Worthy of C-Level Executives
When Generation Z discovers they can swap the tie for a megayacht and still earn an executive salary, the corporate world begins to lose its luster.
In December, at 28 years old, Cassidy O’Hagan gazed at the crystal blue waters of the Maldives, staying at an ultra-exclusive resort, in a bungalow all to herself, with a private chef and everything covered. This was not a vacation — it was work. The young woman from Colorado was not on a corporate mileage program, but rather working as a nanny for a super-rich family, part of a world that many in the Generation Z are choosing instead of the traditional office career.
The information was revealed by Business Insider, in a report by Emmalyse Brownstein, showing how nannies, personal assistants, drivers, house managers, and private chefs are becoming the new “dream job” for a segment of young people who, tired of mass layoffs and burnout, have started aiming for something very different from the boardroom: the behind-the-scenes of mansions, private jets, and megayachts of billionaires.
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From Frustrated Doctor to Six-Figure Nanny for Super-Rich Families
Cassidy grew up believing her future was in medicine. She imagined that by her 30s, she would be finishing medical school and solidifying a career in healthcare. However, in 2021, after going through offices, clinics, and a job in orthopedic medical sales, she decided to hang up her lab coat and bet on something that seemed, at first, “less serious”: working as a nanny for ultra-wealthy families.
She had already had an initial experience in 2019, at 22, when she was looking for a way to supplement her income while studying for the MCAT, the medical school entrance exam in the US. The plan was temporary. However, upon moving into a mansion of a family in California, she realized she had entered a completely different universe.
In the interview, the job details were vague. The description only mentioned “covered meals.” Upon arrival, Cassidy discovered that this meant having a resident chef, responsible for cooking not just for the family, but for the entire household staff. She was part of a “childcare team” with four nannies, catering to a couple in their 30s, heirs to a large business family. There were also personal assistants, a household staff chief, a team of housekeepers, and even a dedicated home organizer.
Despite all this structure, Cassidy still held the idea that “being a nanny was not enough” as a long-term career. Therefore, in 2021, she decided to force herself to follow the “correct” path in the eyes of many: she accepted a job at a large medical sales company in New York, with a starting salary of US$ 65 thousand a year — an amount that, in one of the most expensive cities in the world, doesn’t go as far as it seems.
The result was classic: exhausting hours in surgeries and hospitals, a heavily male-dominated environment, constant pressure, and the feeling of being invisible. What, in theory, was a “prestigious career” turned into burnout.
Meanwhile, in the world of the ultra-wealthy, opportunities were exploding. Back in the world of “private staffing” — the term used to describe the entire infrastructure of staff that keeps the lives of the ultra-rich running — Cassidy began to gain not only freedom but also much more money. Today, as a nanny for ultra-wealthy families, she has a six-figure salary, with 401(k), health insurance, PTO (paid time off), and earnings between US$ 150 thousand and US$ 250 thousand per year (range she does not detail due to a NDA, non-disclosure agreement).
Additionally, she accumulates benefits that no corporate wellness program offers: meals prepared by a private chef, “nanny wardrobe” (a complete wardrobe paid for by the family), access to drivers, trips on private jets, seasons in Aspen, summers in the Hamptons, trips to Puerto Rico, India, Dubai, and weeks sailing on a “mega, mega yacht” around Europe.
No wonder, she sums it up: “My job in medical sales could never compete with this.”
The Silent Empire of Private Staffing: Billionaires, Superyachts and a Staff Army
This glamorous lifestyle is the visible tip of a gigantic system called private staffing. It is the network of professionals that takes care of everything involving the homes, jets, helicopters, and yachts of the ultra-rich: nannies, executive assistants, personal assistants, house managers, butlers, security personnel, chauffeurs, private chefs, organizers, trusted drivers, and much more.
According to Brian Daniel, founder of the Celebrity Personal Assistant Network, when he opened his agency in 2007, there were very few staffing specialists for the super-wealthy. Today, he estimates there are around 1,000 private staffing agencies worldwide, with about 500 in the United States. In his words, “the appetite is insatiable” and “the depth and breadth of this wealth are simply staggering.”
This is not a coincidence. In 2000, there were 322 people on the Forbes billionaire list. Today, there are over 3,000. Additionally, a recent report from UBS discusses the “rise of the average millionaire”: the number of people with between US$ 1 million and US$ 5 million in investable assets quadrupled in 25 years, reaching 52 million individuals worldwide.
As more billionaires and multimillionaires emerge, so do more mansions, jets, helicopters, and megayachts — and all these assets need a full-time staff. In an increasingly “winner-take-all” capitalism scenario, where tech companies offer nine-figure packages to the best AI researchers, and names like Elon Musk are on the path to becoming the first trillionaires on the planet, traditional corporate life, marked by mass layoffs, reorganizations, and uncertain careers, loses its appeal in the eyes of Generation Z.
Many young people look at this reality and conclude: if they can’t compete with the ultra-rich, maybe it’s better to serve them — and be well paid for it.
The market proves this trend. The website of the agency Tiger Recruitment, which specializes in elite positions, has advertised roles such as:
- Housekeeper with a salary of up to US$ 120 thousand;
- Nanny with compensation of up to US$ 150 thousand;
- Head of personal assistants, with a range between US$ 250 thousand and US$ 280 thousand;
- Director of residences, responsible for coordinating homes in New York, East Hampton, Aspen, and Bel Air, earning between US$ 200 thousand and US$ 250 thousand.
Besides the high salaries, there are bonuses that seem straight out of a movie: guest house available for the employee, company car, retirement plan, stable hours, and in many cases, access to a lifestyle that visually approaches that of the employer — even if only “borrowed.”
Generation Z Against the Cubicle: Statistics, Frustrations, and the Escape from Corporate Careers
Cassidy’s story is not an isolated case. It reflects a widespread sentiment in Generation Z. A survey by Deloitte, of 2025, shows that only 6% of young people in this generation claim their primary career goal is to reach a formal leadership position. Many even avoid taking on leadership roles — a phenomenon dubbed “conscious unbossing” — to preserve the balance between personal and professional life.
At the same time, this generation’s financial expectations are high. According to a survey by Empower, young people define financial success as having a salary around US$ 600 thousand per year, nearly six times more than baby boomers pointed as their ideal target.
This contrast between expectation and reality becomes even more painful in a job market that, in the United States, faces slowing hiring, especially in office positions, while AI advances on administrative, analytical, and even creative tasks. Many recent graduates find themselves, therefore, unemployed, underemployed, or stuck in positions that offer neither growth prospects nor the standard of living they envisioned.
It is in this void that private staffing emerges as a highly attractive “secret” alternative. Brian Daniel states that historically, people “fell into” this career by accident. However, today, the profile of candidates has changed: they are younger and highly qualified. He receives emails from people with PhDs, former lawyers, former business owners, and former real estate professionals. People who, in theory, had the corporate route mapped out but decided that it makes more sense to cook for a billionaire in the Hamptons or organize a celebrity’s schedule in Los Angeles.
An emblematic case is that of Julia Dudley. At 26 years old, she holds a degree and a master’s in communication, and after that, she decided to attend culinary school. She tried life in a communication agency and in restaurants but ended up building her own meal prep business and migrating to work as a private chef.
“I thought: okay, I can set my own hours, earn more money, and be my own boss,” she says. “This is infinitely more interesting than being in a restaurant line.”
In recent summers, Julia has cooked for families in the Hamptons. According to her, preparing two or three meals a day for a few months can earn a six-figure salary. Brian Daniel confirms the trend: “Many chefs leave five-star restaurants to go into private service. We know how long and exhausting the routine in the kitchen is; when they become private chefs for a billionaire, they can triple their salary.”
Megayacht, Yes, But With Floor Rags and NDA: The Other Side of Serving Billionaires
If on one hand salaries, trips on private jets and cinematic mansions entice Generation Z, on the other, working for billionaires is far from a fairytale. The package comes with extreme pressure, unpredictable hours, and a level of responsibility that often exceeds that of a job in investment banking.
Ruth Edwards, a recruiter from the agency Tiger specialized in family offices and homes of ultra-high-net-worth clients, warns: “The reason you are paid so well is that you are expected to be available outside of traditional 9-to-5 hours, and in many cases, you will work long hours.”
Brian Daniel reinforces this: in the industry that serves celebrities and billionaires, you need to have “a lot of energy” because everything happens “at breakneck speed.” It’s common to have to solve last-minute problems, reorganize entire trips overnight, or respond to urgent messages at completely illogical corporate hours.
Moreover, there is a tacit and non-negotiable principle: you are there to do whatever is necessary for the “principal”, a term used in the sector to refer to the client. Daniel gives an example that illustrates well the contrast between glamour and reality:
If the housekeeper has already left and the dog poops in the living room while you are alone with the VIP, someone will have to clean it up — and that someone could very well be you, the same professional who hours later will be next to the boss helping to close a US$ 50 million deal in a movie studio.
But that’s not all. Most ultra-high-net-worth families require their staff to sign extensive NDAs (non-disclosure agreements) and maintain impeccable presence on social media. No compromising photos, controversial comments, or excessive exposure. Discretion is as valuable as technical competence.
The pressure can be as high as — or even higher than — on Wall Street. Daniel himself recalls an episode in which he had to go to the hospital with a panic attack after a particularly tense day working as an assistant.
Cassidy also feels the emotional weight. One of the biggest challenges, according to her, is the mix of personal and professional life. “You are not just working for a family, you are living alongside them, immersed in their rhythms, dynamics, and intimate moments,” she explains. Even acting as one of eight nannies across multiple international residences, the feeling of loneliness is real. She has spent Christmas, Thanksgivings, birthdays, and family celebrations away from her own, always following her employers’ routines.
How to Enter This Closed World — And Why Some Never Leave
Another myth that the Business Insider report debunks is that it’s enough to “want it badly” to secure a position in billionaires’ homes. The reality is much harsher: it’s an extremely closed and competitive market.
Due to the obsession with privacy and security, most ultra-high-net-worth families avoid any public exposure when looking for staff. Direct advertisements are rare. Instead, they rely on specialized private staffing agencies to do the triaging, interviews, and “mining” of candidates.
“It’s a very cruel world,” says Cassidy. In many cases, the only way to even meet one of these families is to be represented by a trusted agency. This means going through multiple interviews, background checks, reference checks, and, of course, showing that you understand that absolute discretion is a basic rule.
On the other hand, for those who manage to enter and perform at a high level, the sector offers extremely rapid advancement. Brian Daniel cites the case of a personal driver for a Hollywood actor who, over the course of 15 years, was promoted to personal assistant, then to executive assistant, and finally started co-producing films with the employer, earning what he describes as “fabulous money.”
Cassidy is experiencing a similar trajectory. In just five years, she went from a novice nanny and frustrated medical student to a top nanny for some of the richest families in the world. Now, she plans her next step: gradually moving away from being a nanny, starting her own private staffing agency, and creating a mentorship business for young people wanting to enter this market. The goal is to gain more autonomy, have the flexibility to start her own family, and at the same time, stay connected to a segment she finds highly rewarding.
She is not the only one pulling other young people into this universe. College classmates, friends working in corporations in New York, and “younger girls” she knows keep asking how she got to where she is. Recently, Cassidy encouraged her own younger brother, who spent a few years working in media and public relations, to make the transition. Today, he works as an assistant to a “celebrity esthetician” in Beverly Hills.
Ruth Edwards did something similar: seeing her 25-year-old son being laid off from a traditional administrative job, she suggested he try life in private staffing. “If you’re struggling in that office environment, go see the world,” she said. Today, he works as a deckhand on a superyacht, traveling the seas while gaining experience in a quietly growing market.
For Cassidy, this career has offered something rare in modern corporate life: stability, meaning, and a level of personal connection that she hadn’t found anywhere else. The megayachts, private jets, and luxury resorts are, of course, powerful perks. But, behind the shine, what keeps many young people from Generation Z on this path is the feeling that, by serving the ultra-rich, they can build the life that the corporate world promised — and failed to deliver.
In the end, this course correction, described by Emmalyse Brownstein in Business Insider, shows a clash of generational expectations. While companies still try to convince Generation Z that it’s worth competing for every rung of the traditional hierarchy, nannies, personal assistants, and private chefs are already living another version of success: with megayachts, guesthouses, company cars, six-figure salaries, and, above all, the feeling that they have better control over their professional destiny.
Would you swap the suit and badge for a life among mansions, private jets, and megayachts working for billionaires?
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