Chase Gallagher was 12 years old when he started mowing his neighbors’ lawns in Chester County, Pa., for $35 a pop in the summer of 2013. At first the Gen Zer had only two customers, but thanks to some aggressive leafleting, he had 10 clients by the following year.
Today, Gallagher’s landscaping business employs 10 people and does “everything from stormwater management and drainage work to pavers and lighting,” he says. Last year, CMG Landscaping generated more than $1.5 million in revenue; meanwhile, many of his peers were still finishing their bachelor’s degrees.
It’s rare, of course, for an old-school pocket-money job to become so lucrative. But Gallagher says it’s exactly what he’s been plotting since the age of 10. “No one would hire me, because in the state of Pennsylvania you have to be 14 to get a job,” the now 23-year-old recalls. “In between school, I would sit there on the couch, and I remember I’d be googling, ‘How to make money.’”
Gallagher’s childhood hustle fits the classic founder narrative. What’s just as striking is his attitude toward traditional employment. Looking back, he thinks following his parents’ preferred path—attending college and then landing a steady job—would have been a bigger risk than going solo. “My mom has been laid off from five different jobs,” he says. “I have way more potential betting on myself than going to work for someone.”
For the generation that grew up playing on a smartphone instead of climbing trees, Gallagher’s beliefs are surprisingly common—and turning one’s hand to entrepreneurship isn’t at all far-fetched.
The second-fastest-growing job title among Gen Z grads right now is “founder,” according to LinkedIn. Nearly two-thirds of people ages 18 to 35 say they’ve either started a side gig or plan to start one, according to research from software firm Intuit—and nearly half of those surveyed say their primary motivation is to be their own boss.
For many people, of course, self-employed success will only ever be an aspiration. Still, Gen Z’s beliefs represent a seismic shift from the attitudes of millennials or Gen X, who tended to gravitate to conventional career paths. And it poses a major obstacle to business leaders in their quest to attract top-notch young talent.
“My generation doesn’t want to go work a consulting or banking job,” says Steven Schwartz, a 26-year-old serial entrepreneur whose latest venture, Whop, is a marketplace for digital entrepreneurs like himself. “They want to make content online, they want to find customers online, and they want to find friends online, because the internet is so powerful.”
"We're used to figuring shit out on our own"
Experts told Fortune that technology, social media, and witnessing millennial burnout have helped drive Gen Zers to ditch corporate careers in favor of going it alone.
A generation ago, creating a shop front and marketing your business would have required renting a physical space and splashing out on ad space in your local paper. Now entrepreneurs don’t even need to leave their homes to create a website on Squarespace, sell directly to their customers on TikTok, and catch up with contractors or clients anytime on Zoom. Gen Zers, the oldest of whom were born in the late 1990s, have barely known a world without those tools.
“There’s so much more infrastructure available for people who want to create things of their own,” says Natasha Stanley, head coach at careers site Careershifters.org, adding that there’s been a “democratization of access to the entrepreneurial world.” Pandemic-driven remote work and schooling, meanwhile, made working for yourself feel that much more attainable.
“Why is [launching a business] easier now than ever before? Because 20 years ago we didn’t have this here,” Gallagher says, pointing to his phone. “This device has made me millions of dollars because it’s helped me market my business; it’s helped me connect with crazy types of people. I can go online today and pay 400 bucks and have an LLC.”
Social media, meanwhile, has given Gen Z a candid view of the working world that previous generations never had. Millennials in droves signed up for college on the promise it would lead to a lucrative career, only to face dimmer chances of being hired in the wake of the Great Financial Crisis, along with salaries that don’t quite stretch like their parents’ did. They’ve been complaining about the situation online for the better part of a decade.
“Gen Z is seeing people talk about burnout, and they’re thinking, ‘If that’s what’s coming, I would rather design a career that actually serves me, versus working myself into the ground for somebody else’s benefit,’” Stanley says. Some older Gen Zers have already seen how fragile a “secure” career can be: Stanley cites a client who was compelled to go freelance after losing her job in the hospitality industry during the pandemic. People whose jobs have been erased by factors beyond their control “want to be able to make decisions and dance with uncertainty in a way where they’re calling shots,” Stanley says.
Brooklyn-based Schwartz got the taste for entrepreneurialism at 13, when he wanted a pair of high-end sneakers—the Nike Kobe 7 Easter shoe, to be exact—but his parents wouldn’t pay for them. He found a likeminded teen on Facebook, Cameron Zoub, to help him build a bot that would buy limited-edition sneakers before they sold out.
Since then the duo have started at least 22 side hustles. Their latest venture, Whop, is now Schwartz’s full-time job. Since the platform launched in 2021, over 5.5 million users have signed up to sell their skills; those freelancers have made a combined total of $723 million, according to the company’s website.
"Gen Z is seeing people talk about burnout and they're thinking, 'I would rather design a career that actually serves me.'"
Natasha Stanley, Head Coach, Careershifters.org
Older managers may argue that young people need to earn the right to autonomy, flexibility, and authority in their field, but Schwartz disagrees. Having had just two “real jobs” before founding Whop, he remembers being shocked when his friends told him they couldn’t simply tell their manager what they’re working on on a given day.
My generation grew up with their phone first, and with an iPad and with the computer, they’re used to figuring shit out on their own,” he explains. “They don’t need to have somebody tell them what to do. They know that a lot of times, they’re going to know a lot more than their manager.”
Moonlighting as CEOs
Of course, the gulf between aspiring to be your own boss and actually doing so can be wide. According to an extensive survey by online freelancer platform Fiverr, some 70% of Gen Zers say they are freelancing or planning to—but less than 5% are actually doing it full-time.
For many, “founder” is just a title on their Instagram or TikTok bio. “I have a bunch of peers who want to start a business, or they have a main job and have an LLC, but there’s no action,” Gallagher says. “I think a lot of it’s just talk.”
Tobba Vigfusdottir, a psychologist and the CEO of Kara Connect, a workplace well-being platform, says young people are mirroring what they see on social media. If everyone on their feed is calling themselves founders and highlighting their side hustle, they’ll want in. “Saying ‘I’m managing a team’ is not a fun story to tell,” she notes.
That said, thanks to the explosion of remote and flexible working, twenty-somethings can have it both ways: They can boost their income by launching side hustles online, with little risk. Many are dipping their toes in entrepreneurial waters, building founder-and-CEO skills from scratch—while still getting a 401(k) and health insurance.
“A lot of Gen Z who come to us are interested in a portfolio career,” Stanley says—one that would spread their risk, “in the same way as if you were buying stock and shares.”
"That might be starting multiple businesses,” she continues. “It might be having one employed income stream and running something on the side.”
Fashion influencer Khadijah Oliver is a case in point. She has over 64,000 followers on her TikTok channel (deedeesade_) and regularly collaborates with the likes of Old Navy and Abercrombie & Fitch.
But the 27-year-old from Houston is also a licensed chiropractic doctor. “No one can ever take that from me,” she says. “That’s my security blanket.”
Oliver has also leveraged an online side hustle into a passive income stream—a gig almost unthinkable a decade ago. She’s the CEO of K. Sade Kollection, a hair-product drop shipping company; that business model lets her sell products on her social media platforms without the headaches of managing inventory or shipment, which are processed by ecommerce companies like Alibaba. It’s on her vision board to create content full-time in 2025, while making “sleep coin” by selling wigs, extensions, and hair products directly to her fans. But, she notes, “if all else fails, I can always be a doctor.”
Getting older, going corporate?
The advantages these entrepreneurs gain from being tech-savvy and very online are matched by the sense of invincibility that comes with youth. Most of them aren’t really worrying about missing out on retirement savings or the safety net of health insurance if they ditch traditional employment.
As they get older and accrue kids and mortgages, plenty of Gen Z founders will end up in the corporate fold. But they won’t be resigned to a nine-to-five grind: After having been their own boss, they won’t want to give up working when and where they’re most productive.
That means businesses, too, will have some growing up to do to attract talented entrepreneurial Gen Zers. “Companies really need to wake up and smell the coffee,” Vigfusdottir says, warning that the most ambitious of the next generation of workers will either leave companies that refuse to adapt or become future competitors with their own innovative ventures.
“The companies that will survive are listening and letting them in, because they’re changing things,” she concludes. “We should be asking them, ‘Can we do things differently?’” The answers, experts agree, will involve building strong intergenerational relationships, giving Gen Zers both clear responsibilities and a degree of autonomy, and being mindful of the generation’s well-founded concerns about well-being.
Employers may also want to leave room for side hustles. Oliver, the Houston-based influencer, believes her generation will always want them. “The typical job is going to be outdated in the future,” she adds. “It’s going to be more of a creative era, more meaningful, with more time to stay with your family, more time to show people the experiences that you have in life—and do that on your own terms, while finding financial freedom by showing up online.”
“It’s not about the money at my age,” Gallagher says. “It’s about the relationships I’m building and the knowledge I am gaining. As an entrepreneur, as someone that builds teams and brings in revenue, the wisdom I’m gaining is exponential compared to if I had a W-2 job.
How big companies can woo Gen Z talent
Take employee well-being seriously
Gen Zers have watched previous generations burn out, and many already struggle with their mental health. Providing direct access to mental health and well-being services is essential. Beyond that, Natasha Stanley of Careershifters.org urges bosses to build “a culture of integrity, respect, and trust.”
Get your boomers and Gen Z workers talking
Tobba Vigfusdottir, CEO of Kara Connect, a workplace well-being platform, recommends that leaders embrace intergenerational networking events and mentorship: “This helps Gen Z understand workplace dynamics, contribute to digital transformation, and shape a culture fit.”
Set clear expectations
Gen Zers want autonomy and are eager to contribute. This can be a great asset—if properly harnessed. Vigfusdottir advises employers to clearly define Gen Z staffers’ roles and explain how to funnel their ideas through appropriate channels, to avoid having to manage an army of headless chickens.
Tap the new kids for ideas
Don’t be afraid to lean on bright young minds. “Give them space and a voice to open up new ways of thinking,” Stanley says. Vigfusdottir recommends taking advantage of Gen Z’s digital native skills, involving them in any AI initiatives, and more broadly in reimagining your business’s use of tech.
This article appears in the February/March 2025 issue of Fortune with the headline "Gen Zers want to be their own boss. Can the corporate world woo them back?"
