Middle-Aged Millennials

Older millennials made it to management—now they're wondering if they even want to be the boss


As millennials begin to turn 40 in 2021, CNBC Make It has launched Middle-Aged Millennials, a series exploring how the oldest members of this generation have grown into adulthood amidst the backdrop of the Great Recession and the Covid-19 pandemic, student loans, stagnant wages and rising costs of living.

Millennials have gotten a bad rap since they started entering the workforce. They have been stereotyped as lazy and entitled employees who will trade company loyalty for the ability to leapfrog into a management position they haven't earned; they want to work for a values-driven company with a casual dress code.

But the reality is that many millennials went to college at a time when education costs soared and graduated into a financial recession that gave them limited career opportunities to pay off their student loans, let alone save for other financial milestones.

Then, companies began to eliminate middle management jobs — the ones millennials were working toward — as the job market tanked during the financial crisis. Senior leaders who weren't pushed out of work delayed their retirement. At the very top, CEOs got older, stayed longer and got a lot richer.

Now, millennials are the largest generation in the workforce, and the oldest among them turn 40 this year. This comes as the number of management roles held by people younger than 45 is about the same as for those above that age, according to the Bureau of Labor Statistics.

But many millennials are now rethinking whether climbing the corporate ladder is really worth it after spending their early careers burning out on limited opportunities.

The responsibilities of managing aren't always equal to the benefits

Though millennials have been stuck with the reputation of being job-hoppers, the reality is that young workers in their late teens into their early 20s are just generally more likely to try out more jobs as they figure out their careers. This has been true of young workers from any generation — including baby boomers, who have been stereotyped as hard-working loyalists. What's different for millennials may be how it has become the top strategy to actually get ahead in their careers.

Job-hopping for the sake of advancement is something Jayde Young, 33, knows well. The marketing executive worked for major corporations in New York City including Viacom, MGM and New York Magazine, spending about a year or two at each before moving to a different employer.

Jayde Young says moving up in her marketing career came at a big personal cost: Time lost with family, a stressful schedule, and a path to burnout that exacerbated a chronic illness.
Courtesy of subject

Young describes her experiences, and the ones she's heard from countless peers, in this way: "You'll work really hard and they'll enjoy your efforts, but when it comes time to discuss a promotion, they don't want to promote you unless they see you're being scouted by another company."

"What determines promotion rates is mainly company growth rates," Wharton School researcher and management professor Peter Cappelli says. Because business growth has been slow in the last 20 years, it's likely promotions have taken longer, he says.

At the same time, employers have redirected their attention to recruiting. "Companies are filling a hugely disproportionate share of vacancies from the outside" to stay competitive, Cappelli says. "As it got easier to hire from outside, opportunities to develop internally began to decline."

Young has spent the last four years in a managerial role but doesn't relish the idea of being anyone's boss.

"I think it just naturally happened, and I like being challenged," Young says. "Being a manager, it's OK. But it affords me nothing. I don't have any real additional perks that my direct reports don't have. My salary is a little higher, fine, but I have to work a lot longer. Honestly, the title is all fluff at the end of the day."

Many people look at me and husband and say, 'Wow, they made it, they're so successful and both make six figures.' But we're stressed the hell out.
Jayde Young

Young says moving up has come at a big personal cost: 70-hour workweeks, cross-country business trips, missing her kids' school plays. It's a road to burnout that her doctor now says contributed to a chronic illness.

"I don't mean to sound ungrateful," she says. "I've had a great career. But there's a sense of disillusionment when you actually get there."

"My big gripe is us millennials have to work so hard, yet we're saddled with debt and forced to work without any semblance of job security," Young adds. "Many people look at me and husband and say, 'Wow, they made it, they're so successful and both make six figures.' But we're stressed the hell out."

Young's corporate burnout led her to focus on her own self care; this turned into a side hustle of selling bath products through her company ZennBoxx. After developing it for the last five years, she's now in the process of making it her full-time job.

How the pandemic could change millennials' paths to leadership

Millennials' career paths could be shaken up even more following a second once-in-a-lifetime economic downturn during the Covid-19 pandemic. Already, 59% of older millennials have had their income impacted by the pandemic, according to a recent survey conducted by The Harris Poll on behalf of CNBC Make It. Of the 1,000 U.S. adults ages 33 to 40 polled, 23% had their hours reduced, 15% had their wages reduced, 15% are working more hours, and 11% were laid off.

A healthy economic recovery could mean more baby boomer executives retire and make way for younger leaders, Crist Kolder Associates principal Kristy Honiotes says.

More flexible workplaces following the pandemic could also encourage millennials to pursue the management track.

In Sacramento, California, 37-year-old Jessica Kriegel has made a career of dispelling the myths and stereotypes of millennial workers as a workplace culture strategist. But for a long time, she didn't think she wanted senior leadership for herself.

"I didn't want to be a boss because when I used to report into a boss, I knew how challenging and demanding the company was on their time," Kriegel says. "I wasn't interested in having that work-life balance."

Jessica Kriegel believed moving into management would hinder her work-life balance, until widespread remote work became more common.
Courtesy of subject

However, now that working from home is more common, many are for the first time claiming the power to set better boundaries around their work and their personal lives.

"With Covid, it feels like the demands are going to be less intrusive, and being a boss could be more possible," Kriegel says.

In early April, Kriegel left her organizational development job at Oracle — where she had been for nearly nine years — and took a new job as the chief people and culture officer for Experience.com. She says one reason she accepted the C-suite job is because she can do it from home.

Indeed, many millennials have continued to move up in their careers throughout the pandemic. However, education level plays a role. According to the CNBC Make It/Harris Poll survey, 47% of those with a bachelor's degree say they were recently promoted in the last year compared with 26% of those without a bachelor's degree.

As for figuring out whether millennials are top management material, Kriegel cautions against making generalizations that her peers are all having difficulty rising through the ranks, or that everyone wants to get there at all.

"It depends on the millennial, their drive, and the company they work for," Kriegel says. "I'm sure some want to be boss, and some don't, and some change their mind. I decided I didn't, and changed my mind."

When millennials get promoted, it's not always enough to get them to stay

For Jerry Won, 37, becoming a manager wasn't enough to get him to stay with his employer. The LA resident graduated from college in 2004 and spent the first chapter of his career in sales, jumping jobs every year across real estate and insurance. By his late 20s, after he met the person who would become his wife, Won decided it was "time to get my act together."

So after six months with one insurance company, he got promoted to a manager role — a record-speed for the company, Won adds.

By his late 20s, Jerry Won traded his sales career for a management role because he wanted to start a family with his wife, Kyunghwa.
Nathan Nowack

The move afforded him more financial stability, more consistent hours, and less anxiety and stress.

But as much as Won loved being a manager, he says, he began to feel boxed in as he realized the company's objectives didn't align with his personal values. "It's ultimately why I left," he says.

Won credits coming from an Asian American household, where his parents raised him to value education and hard work in order to get ahead, for why he quit his job to pursue an MBA. He says "the myth of meritocracy" continued throughout business school, "that if you keep your head down and keep working, you'll get promoted."

But as he looked around and recognized the racial gap in management, and corporate America's slow progress to bridge it, he began to think "maybe the whole system isn't right for me."

So in 2019, Won quit his account director job and became a keynote speaker and independent diversity, equity and inclusion consultant. By 2020, in time for his daughter's first birthday, he launched his Dear Asian Americans podcast, and a few months later founded Just Like Media.

The irony is, this year I'm speaking at these companies and impacting them in far greater ways as an external voice than I ever could have imagined being the guy on the inside.
Jerry Won

For him, the experience has been about redefining what professional success looks like, while also trying to make the work experience a better one for his own children.

Won feels his work has been especially impactful in the last year of rising anti-Asian racism in the U.S. and in the workplace. "The irony is ... this year I'm speaking at these companies and impacting them in far greater ways as an external voice than I ever could have imagined being the guy on the inside."

CNBC Make It will be publishing more stories in the Middle-Aged Millennials series around student loans, employment, wealth, diversity and health. If you're an older millennial (ages 33 to 40), share your story with us for a chance to be featured in a future installment.

Check out:

Meet the middle-aged millennial: Homeowner, debt-burdened and turning 40

More than half of older millennials with student debt say their loans weren’t worth it

Women hit their peak earning years in their 40s: What does that mean for millennials sidetracked by the pandemic?

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