TRACY HEWAT’S FOREBEARS came over on the Mayflower, and their riches grew with the country. Her ancestors owned tracts of land in California and made it big in lumber, gold, and, in particular, a derivative of iron ore. A relative sold the land that would later become the posh town of Bel Air. The family helped found Cal Tech and, as the lore goes, was responsible for bringing Albert Einstein to the US.

By the time the Hewat fortune got to Tracy, the family’s 35-year-old current scion, it had been compounded by Ronald Reagan’s “trickle-down” policies of the 1980s, which provided windfalls to the rich. Today, at the dawn of the George W. era, Hewat feels a sense of déjà vu. “With all the tax-cut stuff in the news, I feel like it’s inevitable that there’s going to be another set of tax cuts that benefit me,” she says. “I’m appalled.”

Daydreams about winning the lottery or getting a big raise are nearly universal in this country. But with the surging economy of the past few years — and now, the worries that the good times might be coming to an end — Americans have been even more obsessed with money than usual. Viewers swarm to “aspirational” TV shows like Who Wants To Be a Millionaire and to Survivor, where “real people” duke it out on a desert island or in the outback to win a million bucks. Darva Conger and a flock of other women even traded their dignity for the chance to be Mrs. Multi-Millionaire. “This is a culture where we think if you marry the millionaire or win the million dollars, it’s the ultimate happiness,” says 25-year-old Karen Pittelman, whose trust fund kicked in four years ago. The shows, she says, “are almost saying a secret truth” about the randomness of wealth: “There’s no difference between inheriting the money I did and answering the right question from Regis Philbin.”

Pittelman is one of a small but growing number of wealthy young people who, with the help of a Cambridge-based nonprofit called Resource Generation, are banding together into what Billy Wimsatt, author of the activist treatise No More Prisons (Soft Skull Press, 1999), dubs the “Cool Rich Kids Movement.” Rather than buying another house or car or yacht, they’re taking the money they — or their parents, or their parents’ parents — worked for, and giving it away to grassroots “social change” organizations.

Resource Generation was founded by Hewat and other Boston-area activists six years ago, after a national conference for wealthy young people was canceled because not enough people had signed up. The problem wasn’t a lack of potential participants — with $10 trillion expected to change generational hands over the next 20 years, according to the Inheritance Project, an online resource clearinghouse, there are plenty of young people with money. Hewat suspected that she knew the real reason for the conference’s failure. “The stereotype of young wealthy men and women was so awful — petulant, greedy, unmotivated,” she says. “No one wanted to fly across the country to go to a conference with people they thought would be like that.”

Many young people are also kept ignorant of their true net worth — or are in denial about it. “Today, it’s easy,” says Hewat. “We look at Bill Gates and people say, ‘He’s rich. If I don’t have that much money, I’m upper middle class.’” But, notes Anne Slepian, co-founder of More Than Money, an Arlington-based organization for wealthy people of all ages, “A lot of people who don’t feel they’re rich at all fall in that wealthiest five percent — and we’re trying to give them a reality check.” She points out that the Federal Survey of Consumer Finances from 1998 (the most recent year available) defines the highest economic echelon as consisting of people with a net worth of roughly $900,000, or an annual household income of $127,000. “Really, that’s two professional incomes in Boston,” she says, “and some 23-year-olds graduating with professional degrees end up earning that amount.”

Resource Generation — which now has two full-time staffers and a one-room office located above New Words Bookstore in Inman Square — is there to serve them. Through a network of referrals and active outreach programs at Tufts University and Hampshire College, the group serves about 250 “constituents” nationwide, who have either inherited wealth (be it millions or thousands) or earned it themselves with high salaries, stock options, or both. The organization — which provides support and strives to build a progressive philanthropic community — holds monthly networking dinners in Boston and Western Massachusetts, and it runs a peer-connection service that links young people going through upper-class rites of passage. “Wouldn’t it be great if folks serving on boards of family foundations could do it with support?” enthuses Hewat. And every year, Resource Generation joins with a number of foundations in sponsoring “Making Money Make Change,” a retreat for 15- to 35-year-old progressives with money. At last year’s conference, they distributed a survey; 45 participants, or about three-quarters of the attendees, filled it out. The total assets they would control over the course of their lives? About $600 million. Says Hewat: “I suspect that’s an underestimate.”

So why do they need a support group? Dennis Pearne, a South Natick–based psychologist who is the author of Wealth Counseling: A Guide for Therapists and Inheritors (Inheritance Project/Trio Press, 1999), explains it this way: “What seems to the public as something that everyone would desire and everyone would welcome has a very difficult, dark side for at least half the people that receive significant wealth.” Inheriting or suddenly earning the equivalent of three months’ salary is enough to “throw people somewhat off-base emotionally,” he says, while people can actually become panicked and traumatized by receiving $500,000 or more. Pearne says that the rich often feel “depressed and isolated” because they’re told to keep their money a secret. “There’s a saying in the Bible about how hard it is for a rich man to enter heaven,” he notes. “The idea is age-old, and in every culture, that there’s something dirty about money.” Money can even lead to fear for one’s safety. “There’s so much paranoia in being raised wealthy,” says Karen Pittelman, who also serves on the board of Resource Generation. “It’s this ‘Lindbergh baby’ philosophy — that everywhere you go, you’re going to be abducted or slaughtered.”

IT’S A SENSITIVE business, organizing these young people. Even activists like Pittelman, who has been open about her inheritance for nearly a year, are squeamish about discussing it. “I still feel like I’m doing something I’m not supposed to, or I’m going to get in trouble,” she says. You have to watch the lingo. Although some are comfortable with the term “rich” — Pittelman is actually in the midst of drafting what she calls a “Radical Rich Kids Manifesto” — others bristle and prefer the more PC term “people with wealth.” Resource Generation calls itself an “alliance” rather than a membership organization because, says Hewat, “it sounds too much like a country club.” Even fundraising — what should be the easiest part of running an organization for the wealthy — is a loaded subject. Jethro Heiko, the co-chair of the Resource Generation board, notes the quandary. “In terms of our values, we don’t want to approach the people we’re providing help to for money,” he says. “They’re struggling with issues and our services are confidential, so we’d have to in a sense solicit from people who are our clients. You can’t do that at first — you have to get to know them. Because the message they get from their families is, ‘Once people know you have money, they’re going to ask for it all the time.’”

A primary goal of Resource Generation, however, is to get young people to give to other organizations. Psychologist Pearne says this is perhaps the healthiest way for the rich to cope with their new identities as people who have become wealthy through work or who, as adults, are suddenly allowed to exercise power over their family fortunes. “Quite often, there’s the question ‘Who am I now that I have all this money?’” he says. “And quite often, a significant part of that answer is philanthropy and social change.” Last year, Tracy Hewat gave away $300,000 to various nonprofits. Karen Pittelman dissolved her $3.5 million trust fund two years ago and started a foundation to help low-income women. Instead of naming it after herself, she christened it the Chahara Foundation, after a homeless girl she befriended when she worked at a Boston day-care center. Even Heiko, one of several nonwealthy members of the Resource Generation board, has been challenging himself to give as much as possible. For the past three years, he’s given a $1000 donation to the tenant-rights group City Life/Vida Urbana in Jamaica Plain, in addition to giving smaller gifts of $50 or $100 to other social-change organizations throughout the year. “I like writing that $1000 check,” he says. “The first time I did that, I was like, ‘This is a trip somewhere, this is rent, this is heat.’ But you get on a budget and you make it work.”

As Karen Pittelman is learning, however, the hardest part of being a cool rich kid may be that — even after the money’s gone — she will, in some ways, always be rich. “It doesn’t matter if I give it away,” she says. “I’ve still got a fancy education, contacts, a whole bag of tricks you can’t lose even if you want to.” She’s ambivalent about her upper-class status, but she recognizes the incredible potential of organizing her peers to work — and pay — for social change. “As much as I don’t like where I come from,” she says, “it’s where I need to do my work.”

Dorie Clark can be reached at dclark[a]phx.com. Resource Generation can be reached at (617) 876-0117 or www.resourcegeneration.org.