When Cassidy O’Hagan gazed across the impossibly clear turquoise waters of the Maldives during a December getaway, she felt a deep and almost surreal sense of accomplishment — as though she had finally arrived at the life she had once only imagined from afar. At twenty-eight years old, she found herself ensconced in a hyper-exclusive resort, occupying her own private villa that offered complete isolation and indulgence. For most people, such a scene might represent the culmination of years of ambition and saving — the epitome of leisure. But for O’Hagan, this was not an indulgence at all; it was quite literally her place of employment.
Through her work as a professional nanny catering to some of the world’s most affluent families, the Colorado native has been transported to destinations she never dared to picture herself in — winters spent among the snow-draped luxury of Aspen, summers in the storied Hamptons, and international assignments that have carried her from Puerto Rico’s beaches and India’s palaces to Dubai’s glitzy skyline and long voyages along Europe’s coastlines aboard what she affectionately calls a “mega, mega yacht.” Her work itself has been a passport to an alternate reality — one that merges domestic labor with high-end travel and exposes her to the lifestyles of those who measure abundance not in millions, but in mansions, jets, and yachts.
Unlike the stereotypical image of a caregiver scraping by, O’Hagan’s position comes with substantial professional benefits: a 401(k), comprehensive healthcare coverage, paid time off, and a salary comfortably within six figures. While legally bound by a nondisclosure agreement, she confirms that her income falls somewhere between $150,000 and $250,000 annually. In addition, there are fringe benefits that only the extremely wealthy could provide — carefully curated meals by private chefs, a tailored “nanny wardrobe,” access to chauffeured vehicles, and travel aboard private aircraft that eliminate the typical hassles of commercial airports. “My old orthopedic medical sales job could never compete,” she admits with a knowing laugh.
O’Hagan’s trajectory wasn’t always headed toward luxury service. She once envisioned herself nearing the end of medical school by this stage in her life. After completing her undergraduate studies, she spent a few years working both in physicians’ offices and within the corporate healthcare world, believing that profession to be her eventual path. Yet by 2021, exhausted and uninspired, she abandoned those plans and joined a burgeoning demographic of Generation Z professionals who were rejecting the sterile rigidity of corporate culture in favor of something that felt more personal, profitable, and dynamic — careers within the private households of society’s ultra-wealthy.
This field, often termed “private staffing,” forms the invisible backbone that upholds the everyday opulence of the global elite. Behind every impeccably run mansion or superyacht exists an intricate ecosystem of personnel — nannies, butlers, personal assistants, estate managers, household chiefs, chefs, security staff, and drivers — all ensuring that the routines of the rich unfold seamlessly. For an increasing number of young, highly educated individuals, such roles offer a lucrative and adventure-filled escape from the unsteady corporate ladder, now perceived as antiquated and unreliable.
Brian Daniel, founder of the Celebrity Personal Assistant Network, recalls that when he established his agency in 2007, specialists like him were rare. Today, he estimates around a thousand private staffing agencies operate worldwide, with roughly half based in the United States. “The appetite is insatiable,” he observes, emphasizing the unprecedented expansion of global wealth. Indeed, we live in what he calls a ‘winner-take-all’ era of capitalism — one where top AI scientists are courted with nine-figure pay packages and titans like Elon Musk inch toward trillionaire status, even as traditional career tracks falter amid widespread layoffs and organizational volatility.
The numbers substantiate Daniel’s claim. In 2000, only 322 individuals graced Forbes’ official list of billionaires; today, that figure surpasses 3,000. Moreover, financial institutions such as UBS have chronicled the ascent of the “everyday millionaire” — individuals possessing between $1 and $5 million in investable assets — whose ranks have multiplied fourfold in the last quarter century. With wealth pooling at the top and luxury assets proliferating, each additional yacht, estate, or jet demands teams of skilled professionals to operate and maintain it. As Daniel notes with pragmatic enthusiasm, “Each of these billionaires employs small armies of people to cater to their every whim.”
The post-pandemic economy has only amplified this need. Intensified competition among elite families for top-tier staff has led to bidding wars that push salaries and fringe benefits ever higher. Daniel describes the offers matter-of-factly: “You need a place to stay? Here’s the guest house. A car? Take the company vehicle. Retirement plan? Done.” Staffing agencies such as Tiger Recruitment echo the trend. Among their listings: housekeepers earning up to $120,000, nannies reaching $150,000, and managerial roles like “head of personal assistants” commanding $250,000-plus annually.
O’Hagan’s first glimpse of this rarefied world came in 2019, when, at just twenty-two, she accepted a nannying position with a California-based family while preparing for the MCAT. What she thought would be a simple childcare position turned into an immersion into an entirely different social and professional universe. “Covered meals,” she soon discovered, meant three-course creations by an in-house chef for both family and staff. Her employers — a couple in their thirties with deep business lineage — oversaw a household orchestrated by a chief of staff and supported by personal assistants, housekeepers, and multiple nannies sharing responsibilities as a ‘childcare team.’
Though she initially viewed nannying as a temporary detour, societal pressures and internalized expectations soon pulled her toward corporate respectability. By 2021, she relocated to New York City to pursue a career in medical sales, entering a demanding, male-dominated arena. The reality — long hours, limited recognition, and an entry salary of $65,000 — quickly eroded her enthusiasm. “I realized that I had walked away from work that actually aligned with who I was,” she later reflected, describing her intrinsic inclination toward nurturing, service, and intuition. Burnt out and underwhelmed, she decided to return to private service full time, this time aiming for the very top tier of clientele.
Partnering with private staffing agencies, O’Hagan soon secured a “rotational nanny” position for a household of prominent New York elites. Her pay instantly increased by $40,000, and once again she enjoyed on-demand meals by professional chefs, designer-clothing allowances, and chauffeured rides to and from work. The contrast with corporate life was startling, and for her, liberating.
Her story mirrors a growing sentiment within her generation. A recent Deloitte survey revealed that only 6% of Gen Z workers identify reaching corporate leadership as their primary goal. Many are even avoiding managerial responsibilities altogether — part of a conscious movement toward “unbossing,” or prioritizing autonomy and mental well-being over hierarchical advancement. Yet their financial expectations remain lofty. A study from Empower found that Gen Z defines financial success as a salary of nearly $600,000 — an aspiration that starkly contrasts with limited early-career opportunities and tightening job markets affected by automation and artificial intelligence.
According to Daniel, private staffing has always been a profession people “fell into” rather than deliberately pursued. What’s new is the influx of highly educated and credentialed candidates — PhDs, former attorneys, real estate professionals — seeking stability, travel, and personal connection outside corporate systems. Julia Dudley, a 26-year-old private chef, illustrates this shift. With undergraduate and graduate degrees in communications and a later stint in culinary school, she left both the restaurant grind and agency work behind, realizing she could earn more and dictate her own schedule by serving private clients. Summers in the Hamptons, she explains, can yield six-figure incomes for those willing to prepare multiple meals daily for a single family.
Even Brian Daniel points out that many chefs from Michelin-starred restaurants are migrating into private service, tripling their income by cooking for billionaires rather than diners. Yet he and recruiters like Ruth Edwards warn that these roles, though financially rewarding, demand resilience and discretion. “This world moves at breakneck speeds,” Edwards says, noting that professionals must always be ready to adapt, anticipate, and execute under pressure. The term “principal” denotes the client, and deference is expected at all times — whether that means taking charge in boardrooms or cleaning up after pets when necessary. Success requires both humility and composure; a single day might include assisting in domestic chores and later helping a mogul seal a multimillion-dollar film deal.
The industry’s code of confidentiality is equally stringent. Employees typically sign non-disclosure agreements, maintain spotless online profiles, and operate in a culture where privacy is sacred. Yet for all its challenges — long hours, demanding schedules, and emotional fatigue — many see the work as offering a sense of stability and adventure that traditional careers lack. Daniel, candid about his own experiences, recalls hospitalizing himself after a panic attack sustained during particularly high-pressure work for a celebrity client. “The stress can be more than even on Wall Street,” he admits.
For O’Hagan, one of the greatest challenges has been the blurring of personal and professional boundaries. Serving families across multiple international estates, she often finds herself deeply enmeshed in their daily lives — participating in their routines, holidays, and even intimate moments. Despite being part of a large team of nannies, the experience can be isolating, particularly when work duties coincide with personal milestones. Christmases, birthdays, family gatherings — she has spent more than a few away from her own loved ones.
Yet despite such sacrifices, O’Hagan believes the private service industry offers exceptional rewards for those adaptable enough to thrive within its structure. Landing elite roles, however, is rarely straightforward. Agencies typically serve as gatekeepers, matching candidates to families and ensuring reputational fit. “It’s a very cutthroat world,” O’Hagan admits, noting that professional discretion, social finesse, and exceptional reliability are prerequisites for entrance into these circles.
For those who excel, upward mobility can be remarkable. Daniel recounts one professional trajectory in which a personal driver for a Hollywood actor earned the principal’s trust over 15 years — eventually being promoted to personal assistant, then executive assistant, and finally co-producer on the actor’s film projects. “He made fabulous money,” Daniel notes, underscoring the potential for growth within such close-knit professional relationships.
O’Hagan herself feels she has achieved what she once considered a distant dream: working for some of the world’s most prominent families within just five years. Now, as she plans for the future, she hopes to parlay her experience into her own staffing consultancy and coaching enterprise — a venture that would allow her to guide other young people seeking similar opportunities while developing the flexibility to eventually start her own family. “Peers of mine in New York, girls I’ve known since college, they reach out constantly asking how I got here,” she explains. She has even helped her younger brother pivot from an unfulfilling media job to a role assisting a celebrity aesthetician in Beverly Hills.
Recruiter Ruth Edwards echoes that sentiment of generational transition. After her 25-year-old son lost his administrative office job, she encouraged him to enter private service. Today, he works as a deckhand on a superyacht, traveling the world while honing practical skills and earning more than he ever did behind a desk.
For O’Hagan, this career path has provided not only material comfort but also an unexpected sense of alignment — a fusion of stability, meaningful human connection, and adventure. “This work,” she reflects, “has offered me a level of purpose and balance that I hadn’t found anywhere else.” In an era where traditional professions are faltering and success itself is being redefined, her story encapsulates a broader truth: for many in her generation, fulfillment no longer resides in the corner office, but within the intricate, high-stakes, and profoundly human world of private service.
Sourse: https://www.businessinsider.com/gen-z-billionaire-private-staff-nanny-jobs-2025-11
