By Lina Irawan 
In an era where artificial intelligence increasingly reshapes industries and the global job market grows more competitive, the existential question of future employment has transcended socio-economic boundaries. What was once primarily a concern for middle-class and low-income families—“Will my kid be able to get a job and support themself?”—is now echoing in the gilded halls of the ultra-high net worth. This shared apprehension underscores a profound societal shift, highlighting that the fundamental nature of work and career progression is undergoing a seismic transformation, challenging even the most privileged assumptions about success and stability.
Tom Thiegs, managing director of leadership and legacy at Ascent Private Capital Management with U.S. Bank, articulates this unique dilemma faced by the affluent. "Billionaires have the financial resources to support their children, but they sometimes struggle to determine what else is needed for their children to succeed," he told Fortune. This sentiment reveals that financial capital alone is no longer considered a complete shield against the uncertainties of a rapidly evolving professional landscape. The conversation has moved beyond mere monetary provision to a deeper, more complex discussion about developing resilience, purpose, and adaptability in their offspring.
Patrick Dwyer, managing director at Aligned by NewEdge Wealth, a boutique firm catering to clients with net worths ranging from approximately $100 million to over $1 billion, echoed this sentiment to CNBC earlier this year. He observed that millionaires and billionaires "are recognizing this is not the same game they had to play." This realization is prompting a fundamental re-evaluation of parental support. "Families have to rethink… what it means to support their children. And we’re not talking about spoiling your kids. We’re talking about: What if your kid needs retraining at 33?" Dwyer’s perspective highlights the shift from a linear career path to one requiring continuous learning and adaptation, a stark contrast to the more stable career trajectories many older generations experienced.
Dwyer’s clients are particularly concerned about their children, typically aged 22 to 35, struggling to secure and retain positions in fields traditionally associated with high status and security, such as technology, law, and healthcare. These sectors, once bastions of white-collar opportunity, are now at the forefront of AI-driven disruption. For instance, AI-powered legal research tools are streamlining tasks traditionally performed by junior lawyers, while diagnostic AI in healthcare is augmenting, and in some cases, beginning to replace, certain functions of medical professionals. In the technology sector itself, mass layoffs, often attributed to efficiency drives and AI integration, have become a recurring headline, shattering the illusion of impregnable job security. This erosion of traditional pathways implies that the wealthy may need to pass on a more substantial portion of their fortune to their children, not merely as an inheritance, but as a lifeline for navigating an unpredictable economic future. Dwyer explained, "[They’re] realizing that if they don’t pass on more meaningful wealth to their children, or their children are not able to accumulate wealth… their kids could have [less] agency over their lives than they did." This concern extends beyond financial comfort, touching upon the very ability of their children to exert control and make independent choices in a world where economic self-sufficiency becomes increasingly challenging.
While this might sound like an almost absurd fear coming from America’s wealthiest, wealth managers are increasingly validating its legitimacy. "This is a very real concern I’m hearing from ultra-affluent families right now," Thiegs affirmed. "On the surface it can sound irrational: ‘Why would a billionaire worry about their child getting a job?’ But realistically, no matter how much money you have, parents still want their children to succeed and lead fulfilled lives." This underscores a universal parental instinct that transcends economic standing—the desire for children to thrive, find purpose, and contribute meaningfully, rather than merely existing on inherited wealth.
Why Parents of Gen Zers Are So Stressed About the Job Market
The apprehension among parents of Gen Z stems from more than just financial stability; it’s rooted in a deeper concern for their children’s overall well-being and sense of self. The volatile job market directly impacts how these parents envision their children’s financial and personal futures, but the core issue isn’t a fear of being unable to provide financial assistance. Rather, it’s a worry that their children will not achieve the same career outcomes, sense of accomplishment, or personal fulfillment that characterized past generations.
"They’re not usually worried about the financial security of their children; rather they worry that the job market will impact their child’s sense of purpose, identity, and confidence," Thiegs elaborated. This speaks to a profound understanding that meaningful work contributes significantly to an individual’s psychological well-being. A lack of engaging employment can lead to feelings of aimlessness, diminished self-worth, and a struggle to forge a distinct identity separate from their family’s wealth. Compounding this, Thiegs added, "They also worry that significant wealth will dampen their drive or desire to work." This is the classic "trust fund baby" dilemma, where an abundance of resources, without corresponding purpose or challenge, can lead to apathy and a lack of motivation.
However, Thiegs doesn’t advocate for simply bankrolling their children indefinitely. Instead, he emphasizes the critical importance of sophisticated estate planning, strategic investing, and long-term financial planning that goes beyond mere wealth preservation. "When parents are worried about their children’s job security, we recommend creating a system that provides opportunities for growth and development rather than just a financial safety net," he advised. This proactive approach focuses on cultivating skills, fostering independence, and instilling a work ethic, rather than passively cushioning potential falls. The emphasis, he added, is on implementing plans that support a child’s self-worth more than just their net worth, recognizing that true success is holistic.
Trent Von Ahsen, a certified financial planner and managing partner at Cedar Point Capital Partners, echoes this sentiment. He observes that his ultra-high net worth families perceive the risks of today’s job market less as a threat to financial stability and more as a challenge to their children’s independence. "This cohort of parents seem more concerned about over-supporting their children, than under-supporting them," Von Ahsen told Fortune. This highlights the delicate balance these parents seek: providing enough support to navigate a tough economic climate without inadvertently stifling their children’s ambition or making them perpetually dependent.
How Gen Z Is Getting Ahead of the Job Market
The current generation entering the workforce, Gen Z, is keenly aware of these shifting dynamics and is already making unconventional career choices that reflect a pragmatic response to an uncertain future. Faced with widespread layoffs in traditional white-collar sectors and an omnipresent anxiety about AI’s capabilities, many young workers are actively eschewing conventional corporate paths. Instead, they are gravitating towards roles they believe offer greater autonomy, faster financial returns, or a more tangible sense of purpose.
One prominent trend is the rise of "creator careers," where individuals leverage digital platforms to build personal brands and generate income through content creation, often bringing in millions from side hustles and openly questioning the necessity of a traditional college degree. This path offers a direct link between effort and reward, bypassing corporate hierarchies and the perceived instability of large organizations.
Concurrently, there’s a significant pivot towards blue-collar jobs and skilled trades—from manufacturing and electrical work to plumbing and other technical professions. This movement is fueled by several factors: the stability and high demand for skilled labor, often leading to six-figure incomes without the burden of student loan debt, and a growing skepticism about the return on investment of a four-year university degree. A 2025 Deloitte global survey underscored this generational shift, finding that only 6% of Gen Z respondents cited reaching a corporate leadership role as a primary goal. Instead, their priorities are overwhelmingly centered on work-life balance, personal fulfillment, and continuous learning, often through unconventional means. This indicates a profound re-evaluation of what constitutes a "successful" career, moving away from status symbols towards intrinsic satisfaction and practical security.
In some elite households, college-educated Gen Zers are even competing for lucrative six-figure nanny and tutor roles, seeing these as viable avenues to achieve financial "freedom" outside the perceived confines and uncertainties of a traditional office career. These roles, often requiring specialized skills and offering attractive compensation, provide an immediate and tangible financial benefit without the long-term career planning complexities of other fields.
These evolving career trajectories necessitate a fundamental rethinking of financial planning for billionaires and other high-net-worth individuals. They must now design financial strategies that "encourage growth and responsibility" rather than solely relying on large, lump-sum inheritances, as Von Ahsen points out. The traditional model of simply passing down wealth is insufficient in a world where adaptability and continuous skill development are paramount.
"We see more emphasis on education funding flexibility, mentorship, and phased wealth transfers," Von Ahsen explained. Education funding flexibility means moving beyond just financing traditional college degrees to supporting vocational training, certifications, entrepreneurial ventures, and lifelong learning opportunities that can help children pivot careers multiple times. Mentorship becomes crucial, connecting the next generation with experienced professionals who can offer guidance, networking opportunities, and insights into navigating complex industries, fostering practical skills and real-world acumen. Phased wealth transfers, instead of a single, large inheritance, involve distributing assets gradually over time, often tied to specific milestones or achievements, thus encouraging responsible financial management and preventing premature squandering. This approach aims to provide financial support as a tool for empowerment rather than a crutch. It’s "really an attitude moving toward providing opportunity without removing initiative," Von Ahsen concluded, encapsulating the delicate balance these wealthy families are striving to achieve: equipping their children with the resources and mindset to thrive independently, without inadvertently undermining their drive or sense of purpose.
The anxieties of the ultra-wealthy, while seemingly paradoxical, highlight a universal truth: the future of work is uncertain for everyone. Their concerns, refracted through the lens of immense privilege, nonetheless reflect a broader societal reckoning with AI’s impact and the need for adaptable, purpose-driven lives in an increasingly dynamic world. The strategies wealth managers are now advising—focusing on personal development, phased financial support, and fostering initiative—offer valuable insights not just for the affluent, but for all parents striving to prepare their children for the unpredictable professional landscape of tomorrow.
