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Rethinking The Dream

From Homeownership To Passion Projects, What ‘Making It’ Means May Depend On Your Birth Year

by

Features

Back in the 1950s, the American Dream meant working hard to build a better life. Today, most millennials, Gen Xers, baby boomers and members of Generation Jones — a lesser-known cohort with birth dates between 1955 and 1964 that’s often considered a bridge between boomers and Gen X — still believe in the same core values. Among these are free speech, owning a home, quality health care and education, a fair justice system and secure retirement. Still, what that dream looks like — and how it is pursued — differs by generation.

Different Generations, Different Priorities

Nicole Carlon, 32, a certified financial planner with WiseOak Wealth in Boca Raton, has seen firsthand how the American Dream looks different for every generation.

“For baby boomers, it’s about security and legacy,” she says. “They’re thinking about long-term care, preserving wealth and creating stability for their children or grandchildren.”

Gen X, Carlon says, is facing a financial squeeze — often helping both their aging parents and children while still trying to save for retirement. 

Millennials, on the other hand, are paying off student loans and facing high housing costs. That’s pushing many to shift their focus. “They want careers that offer a sense of purpose,” Carlon says. “While they still desire homeownership, they’re often more likely to rent longer before buying a home and value lifestyle over tradition.”

Laurie Spector, 47, a realtor at Compass in Fort Lauderdale, agrees that even though the current economy makes it harder, many people still see owning a home in South Florida as part of the American Dream. Luckily, help is out there.

“There are programs that assist first-time buyers with down payments and closing costs,” she explains. “In Florida, we have the Hometown Heroes Program, and some cities also offer help for those earning below 80% of the area’s median income.”

Dream Shift: How Millennials Are Ditching Tradition For Fulfillment

For millennials like Brooke Gale, 29, of Boca Raton, finding purpose in life is just as important as being financially stable.

“My parents both worked incredibly hard and valued service, security and stability for their family,” Gale says. “My generation still values those things, but we also prioritize mental health, creativity and flexibility.”

Gale runs a private mental health practice in Boca Raton and is also a beauty content creator on Instagram.

Despite challenges like student debt, she’s grateful to have built a dual career as both a therapist and influencer — something she says wouldn’t have been possible years ago.

“Makeup is my creative outlet,” she explains. “It’s how I play, reset and tell stories without words. This flexibility to combine my clinical work with my creative passions has reshaped how I think about success and fulfillment.”

Chris Brunette, 37, physician development director for neurology and rheumatology with Bendcare in Boca Raton, says that although he owns a home, many of his peers are choosing to delay or forgo that part of the American Dream. 

“Many would rather invest than take on a mortgage,” he explains. “When you rent, it’s easier. If something breaks, it’s not your problem. For my generation, convenience really matters.”

While work has always been key to achieving the American Dream, younger generations view employment differently. Baby boomers believed in working long hours and saw their job as part of their identity. Millennials and Gen Z, on the other hand, want careers that support their lifestyle, not consume it.

“We don’t want to live and die by the nine-to-five,” says Brunette, who believes that remote work has helped bring about more freedom and flexibility. He also sees more millennials choosing careers they feel are meaningful. 

“Millennials want a balanced life and a career that makes them happy,” he says. “I work in the health care field, and for me that’s incredibly fulfilling.”

Joshua Feller, 42, financial advisor and founder of Feller Financial Services in Boca Raton, agrees, noting that the pandemic significantly shifted work perspectives.

“We used to follow a pretty standard nine-to-five office schedule,” Feller explains. “Now, we give our employees the freedom to work in a way that helps them do their best. That shift to a hybrid home/office setup has improved their productivity and work-life balance.”

Feller says having a clear financial plan helps his clients feel more confident about reaching the American Dream. 

“Once they feel financially secure, they can stop worrying less and enjoy life more,” he explains.

Immigrating To The United States: The Pursuit Of The American Dream

Rachelle Sylvain, 50, CEO and life and wellness practitioner at R-Motivation in Fort Lauderdale, says her Haitian immigrant parents came to the United States in the 1960s to attend college, knowing they’d have to work hard for every opportunity.

“Their American Dream was rooted in education, homeownership and community service,” she says. 

Her father became an architect and urban planner; her mother a chemist and educator — and both deeply committed to giving back. Sylvain grew up with that sense of purpose, but also the freedom to redefine success.

“My American Dream builds on their legacy of service, but it also includes wellness, authenticity and asking if the path I’m on truly aligns with who I am,” says Sylvain, who now helps other women redefine success on their own terms.

“For some women, the American Dream is launching a business, achieving financial independence or buying that home they were told they’d never afford,” she says. “Yet what I see more than anything is a hunger for emotional, spiritual and creative freedom. Women want the power to choose how they live, work, mother, partner and show up in the world.”

Breaking Down Barriers to Achieve the Dream

Alexander Adames, 29, a presidential postdoctoral research fellow in the Department of Sociology at Princeton University in New Jersey, studies the costs of the American Dream. He says Americans without a college degree are finding it harder to achieve certain economic milestones. 

“Multiple studies have shown that the homeownership gap between college graduates and those with no college education has been widening over the last 50 years,” Adames says. 

And while more people are now responsible for their own retirement savings, not everyone can keep up.

“Since 1989, liquid assets for people with only a high school diploma dropped from $18,440 to $12,880,” he says. “Meanwhile, college graduates saw their earnings rise from $78,390 to $157,990. The gap in retirement accounts is growing, too.”

Adames says asset poverty — when a family doesn’t have enough in savings or investments to cover basic living costs for three months if their income stops — is also affecting many Americans.

“In 2022, 45% of U.S. households, including over a third of homeowners with children, lacked enough savings to handle family emergencies,” he says. “They may own a home, but they don’t have the extra money to deal with job loss, medical bills or other financial setbacks.”

Shifting Dreams And Redefining Retirement

At 63, Michele Bellisari, who is a part of Generation Jones, says that over the years her view of the American Dream has changed. 

“It used to be one path,” she says. “But in midlife, it feels more flexible. Now, it means finding new income streams, reinventing yourself and living life on your own terms.”

Bellisari, a realtor with Real Broker, LLC, in Boca Raton, notes that high living costs, record home prices, elevated interest rates and soaring insurance premiums have made it more challenging for many people to becoming homeowners.

“The good news is that the gig economy, digital tools, social media and affiliate marketing have opened new doors,” she says. “Now, people can grow, create, thrive and earn additional income."

Bellisari has done just that by promoting home listings and fun things to do in Boca Raton through her website, soooboca.com, and her social media.

Kathy Criscuolo Boufford, 55, a family attorney in Monroe, Connecticut, and author of “Divorce Matters: What You Really Need to Know When it’s Time to Get a Divorce,” says that while the divorce rate among those 50 and above has doubled since the 1990s, it doesn’t stop anyone from chasing the American Dream.

“Retirement isn’t the end of being productive,” Criscuolo Boufford says. “Many people see it as the start of a new chapter and look forward to their second or third act in life.”

Marlyn Kefauver, 82, lives at Edgewater at Boca Pointe, a continuing care retirement community in Boca Raton. She grew up in a middle-class family in Houston, Texas, and was the granddaughter of immigrants. Kefauver was the first in her family to attend college, and among the first female undergraduates at Georgetown University after it became fully co-ed in 1969.

After college, Kefauver landed a job with the U.S. government, working for the Department of Health and Human Services. She married her husband, David, in 1970, and the two lived in Maryland for 40 years. When he died in 2010, Kefauver moved to Florida, where she and her husband planned to retire. Now, she enjoys the many activities Edgewater offers and is happy she no longer has to worry about home repairs, thanks to the 24/7 on-call maintenance crew.

“When I first relocated to Florida, I lived in a condo but found I was doing everything by myself, except when the kids came to visit,” she says. “I thought I’d be a recluse if I continued to live alone in a condo, but since I moved to Edgewater, I’ve made wonderful friends and found the perfect place to spend my retirement.”