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Millennials Turn 40

Stressed, in debt and in demand, Millennials are rethinking their priorities—and their careers—as they enter middle age.

Happy birthday to the oldest Millennials. They’ve hit the Big 4-0 this year and deserve a party for surviving their early careers.

They’ve endured two economic downturns, including the Great Recession; the aftermath of the 9/11 terrorist attacks; the wars in Iraq and Afghanistan; and the COVID-19 pandemic. Add to that climate change, massive student loan debt, and increasing social and political strife and it’s hardly surprising that Millennials are burdened with monumental levels of stress.

That backdrop has led Millennials, who range in age from 25 to 40, to become skeptical of institutions, including their employers. Many members of this generation also have a healthy self-confidence due to the fact they were raised by so-called helicopter parents who shielded them from disappointment, according to research. 

The combination, critics claim, has produced a generation with a large proportion of people who feel entitled: They demand to know when they will be promoted, continually question established protocols and constantly hunger for praise. Millennials and their allies counter that they’re not so much entitled as emboldened. Realizing that job security is practically nonexistent, members of this generation are hoping to learn as much as possible from their current employers as they proactively plan their careers and seek new opportunities. 

“They aren’t looking to see where they fit in the ladder. They’re thinking, ‘What role does this job play in my life story?’ ” says Bruce Tulgan, founder and CEO of RainmakerThinking Inc., a New Haven, Conn.-based management research, training and consulting firm, and author of Not Everyone Gets a Trophy: How to Manage the Millennials (Jossey-Bass, 2016). “They’re shaped by a different history.”

Molded by Their Environment

Every generation is defined by the major events that took place during their lifetime, and no group has had it easy. Millennials, however, grew up with access to a level of information that no previous generation has had. For example, CNN ushered in the 24-hour news cycle when it was launched in 1980, the year before the first Millennials were born. That may seem quaint compared to having news streaming to your smartphone, but the point remains that Millennials were immersed in facts, figures and data at a relatively young age.

As the largest generation in the labor force today, Millennials have forced employers to bend to their will. And while sometimes maligned by older generations for doing so, they have pushed for policies that create a more employee-centered workplace benefiting people of all ages. Paid parental leave, diversity programs, mental health benefits and corporate responsibility efforts, for example, have expanded as companies fight to attract and retain members of this coveted group. Some companies have also developed student loan repayment benefits to help them.

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‘We thought we were going to change the world, but now I’m not so sure. It’s much harder than you think.’


Yet Millennials are still frustrated. “We thought we were going to change the world, but now I’m not so sure,” says Keahn Gary, senior manager for the Center for the Future of Work at Cognizant, a Teaneck, N.J.-based consulting firm. “It’s much harder than you think.”

Millennials are very tough on themselves and are vexed by the slow pace of change, research shows. Members of this generation want their jobs to have meaning beyond just paying the bills. They worry about their finances, their health and their families. Roughly 40 percent of Millennials say they are stressed all or most of the time, according to Deloitte’s 2021 Millennial and Gen Z Survey report. 

The Great Resignation

Perhaps that’s why Millennials are leading the exodus from the workplace. Resignation rates for employees between the ages of 30 and 45 increased 20 percent between 2020 and 2021—more than for any other age group, according to a study by Harvard Business Review.

They have been preparing for an exit for some time. According to LendingTree, 50 percent of Millennials have a second income stream. For some, it’s a financial necessity; for others, it’s a pathway out of corporate America. The latter can pose a problem for companies as they also deal with large numbers of Baby Boomers retiring, so businesses continue to search for ways to attract and retain Millennials. 

Not all companies are hitting the mark. Jeffery Shipwash says his employer dismissed survey results that showed people wanted to work from home at least part time after the pandemic. “It was completely ignored,” says the 28-year-old, who is a finance officer for the Department of Energy, though he works for a contractor he prefers not to name. “You just have no power at work.”

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Last year, Shipwash started a company that flips houses; eventually, he hopes to make this his full-time job. It’s not exactly what the resident of Kingston, Tenn., envisioned when he graduated from college. His father and grandfather stressed the importance of getting and keeping a good, steady job. But during the lockdown, he realized he was putting his relationships with family and friends on the back burner as he chased the next promotion.

“I was always so career-focused,” Shipwash says. “As soon as I got to one step, I was automatically thinking about the next one. It’s not about money anymore. When COVID hit, it really made me change what I viewed as important.”

 of Millennials are currently searching for jobs, compared with 23% of members of Generation X and 9% of Baby Boomers/Traditionalists.

Source: Harnessing the Great Resignation—Supplemental Research, SHRM, October 2021.


Will Sealy also started his own firm. In 2017, the 34-year-old co-founded Summer, which provides various services to employers to help their workers pay off student debt. “It was so eye-opening to see so many of my classmates struggling with it,” says Sealy, who is delaying marriage until he can pay off more of his debt, which is down to $20,000 from $65,000. He says the typical Millennial has $40,000 in student debt, which requires a payment of $500 a month.

One of Summer’s offerings is creating programs that allow employers to pay back some of their workers’ student loans. Assistance with student debt has become a popular perk in general, with companies such as Aetna, Fidelity and Abbott Laboratories offering it as part of their benefits packages. 

The debt is a drag on Millennials’ lives, affecting everything from their credit scores to where they can afford to get a job. Big cities might offer better salaries, but borrowers may not be able to afford the rent and still make their loan payments.

Sealy says Millennials’ debt has made them wary of promises by institutions. Teachers and counselors told them going to college would lead to higher-paying jobs and encouraged high school seniors who probably had never taken a personal finance course to seek loans they didn’t really understand. “It was like Monopoly money,” Sealy says.

He and his classmates graduated during the Great Recession, and many struggled to find jobs. “I feel like we were misled into thinking that it was all going to work out and be fine,” Sealy says. 

Financially Fragile

The combination of the recession and slow wage growth put older Millennials—those born in the 1980s—in danger of becoming a “lost generation” when it came to wealth accumulation, according to a study published in 2018 by the Federal Reserve Bank of St. Louis. The research, which looked at data from 1989 to 2016, showed that Millennials’ wealth accumulation was 34 percent below where it should have been based on data from older generations. However, they started to gain ground as the economy recovered and are now only 11 percent behind, according to a 2021 report.

That recovery has been uneven, though, with white Millennials and those with college educations faring much better than Millennials of color and those without four-year degrees. Older Black and Hispanic Millennials and those lacking bachelor’s degrees are unemployed at significantly higher rates than their white and more-educated counterparts.

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Diversity Matters

Diversity has been a hot-button issue in the wake of last year’s protests against social injustice. Millennials’ concerns go back further. A 2018 survey by Deloitte found that Millennials and members of Generation Z said diversity was key to workplace loyalty, with 69 percent agreeing that they would stay at an employer for five years or more if they perceived its workforce was diverse.

Deloitte’s research also found that 56 percent of Millennials see systemic racism as very or fairly widespread in society, and more than half see older generations as standing in the way of progress.

Millennials are now the most diverse adult generation in history, according to the Brookings Institution, a Washington, D.C.-based think tank. Generation Z is more diverse, but the oldest members of that generation are 24 this year and don’t yet make up a significant part of the workforce.

Some suggest that Millennials’ diversity will naturally smooth the path to a more inclusive workplace. It’s too soon to say if that will be true as Millennials push further into management, but Millennial-
founded companies such as Meta (formerly Facebook) and Lyft have been criticized for their lack of diversity. Only 8 percent of Lyft’s employees are Black, while 9 percent are Hispanic. Black and Hispanic workers each account for 4 percent of Meta’s employees. 

Millennials of color don’t buy that generational heterogeneity alone will result in more-diverse workplaces. They have faced too much discrimination at work to believe that.

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‘Diversity has to be intentional. This doesn’t just happen.’

“Diversity has to be intentional,” says Alex Tremble, chief culture officer at the American Conservation Experience, a nonprofit that recruits and trains volunteers for restoration projects on U.S. public lands. “This doesn’t just happen.”

Earlier in his career, Tremble found out his supervisor at the U.S. Department of the Interior’s Office of the Secretary was referring to him as her “little Black boy.” He says he sued the department for creating a hostile workplace and won. (A spokesperson for the department had no comment.) Yet he wound up leaving and went on to a career that included seven years with the National Park Service, a bureau within the Interior Department. 

Along the way, the 36-year-old started his own coaching business and a podcast called the Alex Tremble Show. Earlier this year, he left the Park Service because government conflict-of-interest laws were making it too difficult to hold the job while running his business. 

Tremble says part of the allure of his new post at the American Conservation Experience is the ability to diversify what he says is a largely homogeneous environmental sector. He notes that many companies have hired chief diversity officers lately, though he calls a lot of the efforts “fluff” due to these individuals’ lack of power and influence with management.

Tremble says he reports to the CEO, and that’s critical to making changes. He’s currently contemplating how to improve diversity within the organization. Though he still isn’t sure what programs he wants to institute, he knows “we need to think about this differently.”

Rethinking Benefits and Culture

Employers have also needed to look at the workplace through fresh eyes to successfully attract and retain Millennial talent. That’s not easy, as best practices need to be updated and reinforced often. 

“Millennials crave feedback,” says Dan Ballesteros, managing shareholder at Hoge Fenton, a San Jose, Calif.-based law firm. “I think it comes from the ‘everyone gets a medal’ times they grew up with. If you don’t give them feedback regularly, they feel you’re not invested in them.” 

That means Ballesteros is regularly sending out e-mails that recognize younger lawyers’ efforts, which can lead to snarky replies like “thanks for doing your job” from some of his fellow partners, about half of whom are Baby Boomers like himself. At the monthly partners meeting, he says, he sometimes needs to remind those older individuals to keep their attitudes in check. 

Millennials have a different mindset, he notes. When he was a young lawyer, Ballesteros says, he had to prove he was worthy of the firm. But Millennials are “the customer generation,” he explains. “We have to show them why they want to work here.”

That means giving members of this generation opportunities to work on interesting projects beyond the daily grind. “You can’t just give them lousy stuff,” Ballesteros says. “You need to let them interact with the clients.”

The firm has also added a benefit to help these workers pay back their student loans. But Ballesteros says Millennials seem most appreciative of the firm’s decision to reinvigorate its pro bono program at their request. Lawyers can now spend 50 to 60 hours a year working with the public defender’s office. It fulfills the younger generation’s need to have a job that has meaning and allows them to give back. 

“We listened to them,” Ballesteros says. “I think it makes them believe they have a place here.”

Millennials (61%) are more likely than members of Generation X (57%and Baby Boomers/Traditionalists (39%) to say they feel depleted at the end of the workday.

Source: SHRM Mental Health Refresh, 2021.

The Power of Voice

Showing Millennials that their ideas are valued is key to keeping them.

At a town hall meeting during the pandemic with the CEO of Henry Schein Inc., some Millennial employees raised concerns about how dealing with COVID-19 was affecting individuals’ mental health. A mental health committee was formed as a result, and the company added new tools, such as webinars, to help employees cope with stress.

“That was an important initiative, and not just for Millennials,” says Seema Bhansali, executive director, corporate affairs, and co-lead of diversity and inclusion at the maker of medical supplies and equipment. “They were the ones to stand up and say, ‘This matters to me’ in a way that I, as a Gen Xer, never would have done.” 

Over the years, Henry Schein has added other benefits to retain its Millennial workers, such as paying up to $5,000 in adoption benefits and providing four weeks of paid parental leave. Additionally, the education allowance has been raised to $5,000 from $3,500, and plans are underway to create a permanently hybrid workforce. 

Career development is important to Millennials, and Henry Schein also has become more intentional about its training, says Barbara Fisenne, vice president of global organizational development, which includes talent planning. 

Fisenne says the company has been identifying skills gaps in the workplace as it discusses career aspirations with team members. “We want to synthesize these,” she explains. “We don’t just want to throw classes out there.”

Deciding how much effort to put into training Millennials is tricky, RainmakerThinking’s Tulgan says, because “development is an investment paradox. You have to develop people because that’s what they want.” However, the training also makes them more attractive to competitors, he adds, so “you have to calibrate your investment and identify high-performers who are more likely to stay—[and] plan to help them stay longer.”

Notable Millennials Who Founded and Run Companies

Millennials(1) Jessica Alba is a 40-year-old actress turned entrepreneur who founded The Honest Co., a line of clothing, personal-care goods and cleaning products that use sustainable ingredients and no chemicals.

(2) Karissa Bodnar started Thrive Causemetics, a direct-to-consumer, vegan makeup brand, after a friend died of a rare form of cancer. (Thrive’s “clean” cosmetics can be worn by people with compromised immune systems.) The 32-year-old is also the CEO. 

(3) Brian Chesky is the co-founder and CEO of Airbnb. He celebrated his 40th birthday in August.

(4) Daniel Elk is the 38-year-old founder and CEO of music streaming service Spotify. 

(5) Logan Green and (6) John Zimmer started the ride-hailing service Lyft. Zimmer, 37, is the president, while Green is the CEO. Green’s age has been reported as 37 or 38. (The company didn’t respond to inquiries.)

(7) Chieh Huanis the 40-year-old co-founder and CEO of Boxed, which marries the convenience of online shopping with the prices of warehouse clubs, a boon to those who don’t live near a bulk-buy store.  

(8) Kerby Jean-Raymond is the founder of Pyer Moss, a clothing line that has taken the fashion and culture worlds by storm for incorporating political and social commentary into its designs. He is 36. 

(9) Katrina Lake is the founder and CEO of Stitch Fix, a fashion subscription service. She is 38. 

(10) Evan Spiegel and (11) Bobby Murphy co-founded Snap Inc., a social media company with a variety of products, including Snapchat. Murphy is 33 and serves as chief technical officer, while 31-year-old Spiegel is the CEO. 

(12) Whitney Wolfe Herd ­founded Bumble in 2007 and is CEO of the dating app where women make the first move. She is 32.

Career Changes

Some Millennials, longing for purposeful jobs, change careers rather than just positions. Amit Paley is on his third career, and no one is more surprised about it than he is. The 39-year-old says he had wanted to be a journalist since he was a kid and was thrilled when he landed a job at The Washington Post

“I thought I would never leave,” Paley says. But after covering the Iraq War and the Great Recession, Paley was burned out and opted to attend business school. He then became a consultant at McKinsey & Co., where he was a leader in the consulting firm’s LGBTQ resource group. He also volunteered at the Trevor Project, a suicide prevention and crisis intervention organization for LGBTQ youth. 

Paley says he grew up in a liberal, accepting family, yet he still struggled with his sexuality. That led him to think about the conflicts endured by those without strong foundations. 

After Donald Trump’s election, calls to the Trevor Project’s suicide hotline surged because of the former president’s rhetoric and policies regarding the LGBTQ community. 

“It made me think about what gave my life meaning and purpose,” Paley says. No longer content to only volunteer, Paley became the Trevor Project’s CEO in 2017.   

Theresa Agovino is the workplace editor for SHRM.

FROM TOP: Row 1 (Left To Right)—Haleigh Crabtree, Georges Biard / Wikimedia Commons, Agência Brasil Fotografias / Wikimedia Commons, Genevieve / Wikimedia Commons, Albert Nguy; Row 2—Jimmie48 Photography / Shutterstock, Tinseltown / Shutterstock, Cassidy Duhon, Frederic Legrand /Shutterstock; Row 3—Ron Adar / Shutterstock, Dfree / Shutterstock, Bella Saville Photography; Franmarie Metzler / U.S. House Office Of Photography, Dick Thomas Johnson / Wikimedia Commons.

Photograph of Keahn Gary By Bella Saville for HR Magazine.
Photograph of Alex Tremble By Cassidy DuHon for HR Magazine.

SIDEBAR: Courtesy Photos of Notable Millennials.