Nearly half of older millennials wish they’d chosen a different career

With Millennials turning 40 in 2021, CNBC has launched Make It Middle-Aged Millennials, a series that explores how the oldest members of this generation grew up in the context of the Great Recession and the Covid-19 pandemic , Student loans, stagnating wages and rising costs of living.

At 35, Kristen Alfenito complains that she doesn’t have to start her career just yet.

That’s not to say she wasn’t working. She has had a number of jobs over the past 16 years, starting with two part-time appearances while studying music theater. Then, she says, she was diagnosed with cancer, dropped out of college and “for the foreseeable future has resigned to the restaurant or retail trade.” Today Alfenito works as a cashier in a bakery in Morgantown. West Virginia.

When I think back to her college days, “I wish someone had helped me figure out which jobs were right for my interests and passions, and what degree they actually need – if any,” says Alfenito.

Many older millennials now approaching middle age have significant regrets about their careers. Nearly half, 47%, said they would have wished they had chosen a different career path to begin with, according to a recent The Harris Poll conducted on behalf of CNBC Make It of 1,000 U.S. adults aged 33 to 40 Years.

Alfenito believes millennials, who are between 25 and 40 years old this year and represent the largest age group in the workforce, have been pressured to pursue four years of college and the mountains of debt that goes with it, without always knowing if there was one a viable career on the other side of studies.

With older millennials spending nearly two decades in the business, their current roles and responsibilities may not match what they saw in high school or college. We spoke to six people from different areas about what they would do differently if they could start all over again.

A history degree and few job opportunities

For Lee Ruark, getting a history degree was part of a career plan – he just didn’t know what to use his degree for. He graduated from college in 2007 when the economy plunged into the Great Recession and many of the jobs he wanted to try went away with it.

He spent the next three years exploring his options, first considering joining the military until health prevented him from doing so, and then taking LSATs with the intention of studying law. He almost became a police officer before finally stumbling into the substitute apprenticeship. When he found a knack for it, he was certified as a full-time teacher specializing in high school science.

Ruark, now 35 and living in Jeffersonville, Vermont, recalls how stressful it was to be disoriented right out of school.

“I was scared because my friends were finding jobs and I found them very successful while I wasn’t,” says Ruark. “The interesting thing is that after talking to them about it, I found that all of my friends had the same fear of noticing other people’s successes. We laugh about it now, but when we think about it [feeling anxious] was a waste of time and energy. “

If he could, says Ruark, he would go back to when he was in third grade when his mother – also a teacher – told him he had a gift for teaching and encouraged him to pursue it. If he’d listened instead of resisting following in their footsteps, Ruark says he could have completed an apprenticeship much earlier.

A $ 170,000 law degree that didn’t pay off

Some Millennials say the financial realities, especially life with student loans, have changed their chosen career path. As a college senior studying politics, Brad Walters wanted to be a legislative advisor, but given the low starting salary of $ 30,000 compared to his $ 60,000 student debt, he went into education instead. “It says something when education is the more lucrative option,” he jokes.

Brad Walters began an educational career after graduating from law school.

Andrea Tappo

Two years later, he went to law school and went on with an additional $ 170,000 in student loans. But after getting married, having two children, and re-evaluating his career, he left the law and returned to education.

He saw his two options as either becoming an associate in a large law firm, which he didn’t care, or working as an attorney for government or nonprofit organizations, but decided the pay wasn’t worth the hours and perks .

Working in education has given him space to grow and has allowed him to travel extensively, including to Qatar, the United Arab Emirates, Saudi Arabia and China. In the middle of the pandemic, Walters, now 34, got a job as an international school administrator and moved his family to Incheon, South Korea.

Walters says he regrets spending so much money on law school and could have missed the experience.

Don’t take any chances

In Denver, Stephanie McCay, 36, is not thinking about her chosen career but regrets staying so close to home. She was hired for an architecture firm straight out of college, spent the last 15 years building the communications department from the ground up, and is now its director.

“My greatest regret is that I had all these wishes to leave Colorado and go to New York, and I never did,” she says. At the same time, McCay, married, mother of three and homeowner, wonders, “If I had moved, would I have had the same opportunities, or would I have come as far in my career with another big company? I dont know .”

If she could try again, McCay says, she would spend more college senior making connections in New York to start her career there.

Staying in a bad job for too long

Celine Crestin, 39, regretted her career choice until recently. She has a degree in communications and started her career in retail management, then federal government management, but felt unfulfilled and struggled to pay off her student loans. “Then I became a single parent and couldn’t take any risky career steps because I had little to no savings and a lot of debt,” she says. “I don’t think my studies were worth it.”

If she could change something, says Crestin, she would have taken bigger risks in order to have a chance at bigger rewards. “Instead of living in fear when I lost my job due to the recession in 2008, I would have seen it as an opportunity to try something new and take a risk,” she says. Partly due to family commitments and financial stress, “I panicked and had several jobs that I was never satisfied with for years.”

She would also have been better off surrounding herself with more encouraging and supportive people “to motivate myself and build my confidence to take such risks”.

Crestin made the leap to real estate agent in 2017, and after two years of two jobs to make ends meet, she is now making a comfortable living with more work-life flexibility in her second career in Buda, Texas .

A job boom that didn’t work out

Always knowing that she wanted to go into health care, Kristen Conley began reading about various medical specialties in high school. She found some articles predicting a boom in demand for radiologists and enrolled in a private university for a medical imaging program. But in 2010 she made it into a saturated market and struggled to find jobs. Unsatisfied with her options, she returned to school in 2017 for certification as a medical technician, which involves collecting and testing medical samples in a laboratory or hospital.

Kristen Conley, right, and her wife Meisha.


Conley is now 40 years old and works as a medical laboratory scientist in St. Petersburg, Florida, specializing in immunohematology and blood banking. She loves what she does in what she describes as “wide open” with room to grow.

If she could have done it differently, she would have paid less attention to the high of radiology and focused on the stable work of medical technology. “Don’t always believe what you read about a particular job,” she says.

Find the way

While nearly half of older millennials wish they had chosen a different career when they started, data suggests they made their choices and are relatively happy now. According to the CNBC Make It / Harris Poll, a majority, 68%, are happy with their current career path.

Alfenito, the bakery’s cashier, landed with her partner recently in West Virginia via Los Angeles, where she hopes the lower cost of living will help pay off her remaining student loan debt.

She plans to go back to college to study theater – but this time with an emphasis on teaching. “What I was enthusiastic about when I was 19, I still love it today,” she says. “But now I am leaving with the intention of sculpting the heads of tomorrow.”

CNBC Make It will feature additional stories about student loans, employment, wealth, diversity and health in the Middle-Aged Millennials franchise. If you are a senior millennial (aged 33 to 40) share your story with us for a chance to be featured in a future issue.

Check out:

Older millennials made it into management – now they are wondering if they even want to be the boss

‘To the aging 30-year-olds full of regrets in life’: An Open Letter from a Millennial Therapist

Even so, most older millennials are happy with their lives

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