Wealthy parents seem to have it made when it comes to raising their children. They can offer their kids the healthiest foods, the most attentive caregivers, the best teachers and the most enriching experiences, from international vacations to unpaid internships in competitive fields.

Yet these parents have a problem: how to give their kids these advantages while also setting limits. Almost all of the 50 affluent parents in and around New York City that I interviewed for my book Uneasy Street: The Anxieties of Affluence (2017), expressed fears that children would be ‘entitled’ – a dirty word that meant, variously, lazy, materialistic, greedy, rude, selfish and self-satisfied. Instead, they strove to keep their children ‘grounded’ and ‘normal’. Of course, no parent wishes to raise spoiled children; but for those who face relatively few material limits, this possibility is distinctly heightened.

This struggle highlights two challenges that elite parents face in this particular historical moment: the stigma of wealth, and a competitive environment. For most of the 20th century, the United States had a quasi-aristocratic upper class, mainly white, Anglo-Saxon Protestant (WASP) families from old money, usually listed in the Social Register. Comfortable with their inherited advantages, and secure in their economic position, they openly viewed themselves as part of a better class of people. By sending their kids to elite schools and marrying them off to the children of families in the same community, they sought to reproduce their privilege.

But in the past few decades this homogenous ‘leisure class’ has declined, and the category of the ‘working wealthy’, especially in finance, has exploded. The ranks of high-earners have also partially diversified, opening up to people besides WASP men. This shift has led to a more competitive environment, especially in the realm of college admissions.

At the same time, a more egalitarian discourse has taken hold in the public sphere. As the sociologist Shamus Khan at Columbia University in New York argues in his book Privilege (2012), it is no longer legitimate for rich people to assume that they deserve their social position based simply on who they are. Instead, they must frame themselves as deserving on the basis of merit, particularly through hard work. At the same time, popular-culture images proliferate of wealthy people as greedy, lazy, shallow, materialistic or otherwise morally compromised.

Both competition and moral challenge have intensified since the 2008 economic crisis. Jobs for young people, even those with college educations, have become scarcer. The crisis has also made extreme inequality more visible, and exposed those at the top to harsher public critique.

In this climate, it is hard to feel that being wealthy is compatible with being morally worthy, and the wealthy themselves are well aware of the problem. The parents I talked with struggle over how to raise kids who deserve their privilege, encouraging them to become hard workers and disciplined consumers. They often talked about keeping kids ‘normal’, using language that invoked broad ‘middle-class’ American values. At the same time, they wanted to make sure that their children could prevail in increasingly competitive education and labour markets. This dilemma led to a profound tension between limiting and fostering privilege.

Parents’ educational decisions were especially marked by this conflict. Many supported the idea of public school in principle, but were anxious about large classes, lack of sports and arts programmes, and college prospects. Yet they worried that placing kids in elite private schools would distort their understanding of the world, exposing them only to extremely wealthy, ‘entitled’ peers. Justin, a finance entrepreneur, was conflicted about choosing private, saying: ‘I want the kids to be normal. I don’t want them to just be coddled, and be at a country club.’ Kevin, another wealthy father, preferred public school, wanting his young son not to live in an ‘elitist’ ‘narrow world’ in which ‘you only know a certain kind of people. Who are all complaining about their designers and their nannies.’

The question of paid work also brought up this quandary. All the parents I talked with wanted their kids to have a strong work ethic, with some worrying that their children would not be self-sufficient without it. But even those who could support their kids forever didn’t want to. Scott, for example, whose family wealth exceeds $50 million, was ‘terrified’ his kids would grow up to be ‘lazy jerks’. Parents also wanted to ensure children were not materialistic hyper-consumers. One father said of his son: ‘I want him to know limits.’ Parents tied consumption to the work ethic by requiring kids to do household chores. One mother with assets in the tens of millions had recently started requiring her six-year-old to do his own laundry in exchange for his activities and other privileges.

This mother, and many other parents of younger children, said they would insist that their kids work for pay during high school and college, in order to learn ‘the value of a dollar’. Commitment to children’s employment wavered, however, if parents saw having a job as incompatible with other ways of cultivating their capacities. Kate, who had grown up middle-class, said, of her own ‘crappy jobs’ growing up: ‘There’s some value to recognising this is what you have to do, and you get a paycheck, and that’s the money you have, and you budget it.’ But her partner Nadine, who had inherited wealth, contrasted her daughter’s possibly ‘researching harbour seals in Alaska’ to working for pay in a diner. She said: ‘Yes, you want them to learn the value of work, and getting paid for it, and all that stuff. And I don’t want my kids to be entitled. I don’t want them to be, like, silver spoon. But I also feel like life affords a lot of really exciting opportunities.’

The best way to help kids understand constraints, of course, is to impose them. But, despite feeling conflicted, these parents did not limit what their kids consumed in any significant way. Even parents who resisted private school tended to end up there. The limits they placed on consumption were marginal, constituting what the sociologist Allison Pugh in Longing and Belonging (2009) called ‘symbolic deprivation’. Facing competitive college admissions, none of the high-school-age kids of parents in my sample worked for pay; parents were more likely to describe their homework as their ‘job’.

Instead of limiting their privilege, parents tried to regulate children’s feelings about it. They wanted kids to appreciate their private education, comfortable homes, designer clothes, and (in some cases) their business-class or private travel. They emphasised that these privileges were ‘special’ or ‘a treat’. As Allison said, of her family’s two annual vacations: ‘You don’t want your kids to take these kinds of things for granted. … [They should know] most people don’t live this way. And that this is not the norm, and that you should feel this is special, and this is a treat.’

By the same token, they tried to find ways to help kids understand the ‘real world’ – to make sure they ‘understand the way everyone else lives’, in the words of one millionaire mother. Another mother fostered her son’s friendship with a middle-class family who lived in a modest apartment, because, she said: ‘I want to keep our feet in something that’s a little more normal’ than his private-school community.

Ideally, then, kids will be ‘normal’: hard workers and prudent consumers, who don’t see themselves as better than others. But at the same time, they will understand that they’re not normal, appreciating their privilege, without ever showing off. Egalitarian dispositions thereby legitimate unequal distributions, allowing children – and parents – to enjoy and reproduce their advantages without being morally compromised. These days, it seems, the rich can be entitled as long as they do not act or feel ‘entitled’. They can take it, as long as they don’t take it for granted.

Uneasy Street: The Anxieties of Affluence by Rachel Sherman is out now through Princeton University Press.