In a world where artificial intelligence is reshaping entire industries and the job market grows more unpredictable by the day, even America’s wealthiest families are starting to sound a lot like everyone else. Financial advisors working with ultra-high-net-worth clients report a growing and very real anxiety among billionaires and multimillionaires about whether their children will be able to build meaningful, independent careers. The concern may surprise some, but experts say it reflects a genuine shift in how even the most privileged families think about the future. No amount of money, it turns out, can fully insulate a family from the forces rewriting the rules of work.
Tom Thiegs, a director at Ascent Private Capital Management at U.S. Bank who specializes in leadership and legacy issues, has been hearing this worry more and more from some of his wealthiest clients. “Billionaires have the means to support their children, but they sometimes wonder what else it takes for those kids to succeed in life,” he told Fortune. He was quick to acknowledge the apparent contradiction. “It may sound illogical to ask why a billionaire would worry about whether their child can find a job, but parents, regardless of wealth, want their children to succeed and lead fulfilling lives,” Thiegs explained.
Patrick Dwyer, the executive director of Aligned by NewEdge Wealth, a firm that works with clients whose assets range from around $100 million to well over $1 billion, has observed the same trend. He told CNBC that his wealthy clients increasingly recognize that their children are entering a fundamentally different world than the one they navigated themselves. “They understand that the rules of the game are no longer the same as when they entered the workforce,” Dwyer said. His clients are especially concerned about adult children between the ages of 22 and 35 who are struggling to land and hold onto jobs in fields that were once considered stable and prestigious, including technology, law, and healthcare.
The anxiety is less about money running out and more about something harder to manufacture with a trust fund. “It’s generally not about whether the kids will have enough money, but how the current labor market situation will affect their sense of purpose, identity, and self-confidence,” Thiegs said. He also noted that many wealthy parents worry that too much inherited wealth could actually undermine their children’s drive and work ethic. Dwyer echoed this, pointing out that some families are now considering transferring a larger portion of their wealth earlier than planned, precisely because they fear their children may have less control over their own financial destinies than previous generations did. “They recognize that their children might have less control over their lives than they had, if they don’t pass on a significant portion of assets or if the children can’t acquire them on their own,” he told CNBC.
Trent Von Ahsen, a financial planner at Cedar Point Capital Partners, adds an interesting nuance to this discussion. He works with extremely wealthy client families and says the fear is often that parents will do too much, not too little. “This group of parents seems more worried that too much help could become an obstacle than they are worried about not helping enough,” Von Ahsen told Fortune. His recommended approach centers on flexible education funding, mentorship, and a gradual transfer of wealth that encourages ambition rather than dependency. Rather than simply handing over money, the idea is to build systems that open doors and strengthen a young person’s confidence and capabilities.
The broader backdrop to all of this is a generation fundamentally rethinking what a successful career even looks like. Gen Z, facing wave after wave of corporate layoffs and the looming presence of AI automation, is increasingly turning away from the traditional corner-office dream. Many young people are gravitating toward careers that offer flexibility or faster income, from influencer work to skilled trades like electrical work and manufacturing. Highly educated members of Gen Z are even competing for nanny and private tutor positions in elite households, where salaries can reach six figures. A 2025 global Deloitte survey found that only 6 percent of Gen Z respondents identified a corporate leadership role as their primary career goal, with the majority prioritizing work-life balance, personal growth, and a sense of fulfillment instead.
Gen Z, generally defined as those born between 1997 and 2012, is the first generation to grow up entirely in the age of smartphones and social media. This cohort entered the workforce during and after the COVID-19 pandemic, a period that accelerated remote work, gig economy growth, and widespread digital transformation. Economists and sociologists have noted that Gen Z workers tend to change jobs more frequently than previous generations and are more vocal about workplace expectations around mental health and purpose. The rise of AI tools like large language models has only intensified concerns about long-term career stability in white-collar professions, prompting even traditionally prestigious fields such as law, finance, and medicine to reckon with significant structural disruption in the years ahead.
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