A millennial woman who made nearly $250k secretly working 2 jobs says it helped her enter a relationship for the ‘right reasons’ — not financial security

A millennial woman said that secretly working two jobs helped her pay off her student debt, but that homeownership is still out of reach for her in California. The source of the story isn’t pictured.

Two years ago, Olivia was struggling to get ahead financially.

While she was making over $100,000 a year in a communications role, a significant amount of her paychecks was going to her student loans, medical debts, and car payment — leaving little left over for savings — the 37-year-old, who’s based in California’s Bay Area, told B-17 via email.

One day, a former coworker gave her an idea: She could look for a remote side gig to pad her income — and not bother disclosing it to her current employer. So Olivia decided to give it a shot, and it paid off.

Last year, Olivia made nearly $250,000 secretly working her full-time job — which required her to work from the office a few days a week — and a part-time, remote, contract role. She said she collectively worked between 60 and 70 hours in the typical week — including some early mornings, evenings, and weekends — but that the extra hours were well worth the money.

That’s because the extra income helped her pay off the last $20,000 of her student debt, afford an elective surgery her insurance wouldn’t cover, boost her credit score from the 700s to 800s, buy a second car, book a two-week vacation, get a gym membership, and afford healthier food, Olivia said. What’s more, she said the reduction in financial stress that came with a higher income is a key reason she’s in a “healthy” romantic relationship for the first time in over a decade.

However, there’s one area where Olivia’s income still feels frustratingly insufficient: the housing market. She said her combined income isn’t high enough to qualify for many mortgages in the vicinity of her office, where she said the average home price is well over $1 million. In California’s Bay Area cities of San Francisco and San Jose, a homebuyer would need an income of more than $400,000 to qualify for a standard mortgage on a median-priced home, according to a New York Times analysis of Redfin data published last year. What’s more, home prices in the Bay Area have risen even further over the past 12 months.

Additionally, Olivia said the high costs of rent, car insurance, groceries, and utilities in her area have made it difficult for her to save for a down payment. According to an analysis by the online bill-paying service Doxo published in June, California is the second most expensive state in the nation in terms of household bills.

“If employers aren’t willing to pay anyone, even educated professionals, enough to live then they can hardly be surprised that their employees are pursuing multiple sources of income,” said Olivia, whose identity is known to B-17 but asked to use a pseudonym due to fears of professional repercussions.

Olivia is among the “overemployed” Americans who have secretly worked multiple jobs to boost their incomes and job security — B-17 has interviewed over two dozen of these job jugglers. These people have earned as much as $1 million annually across their roles and used the extra money to pay off student debt, afford luxurious vacations, and save for a home. Most overemployed people B-17 has interviewed have been men, in part because IT and tech companies — popular employers for job jugglers due to the prevalence of remote roles — tend to be more male-dominated. However, some women are also working multiple gigs on the sly.

While some companies may be OK with their employees taking on a second gig, doing so without employer approval could have consequences. Additionally, competition for remote roles, return-to-office mandates, and burnout have led some job jugglers to wonder whether their overemployment is sustainable.

Olivia shared how she’s managed to juggle both jobs, why overemployment has improved her romantic life, and whether she thinks her job juggling is sustainable.

Overemployment has helped her pursue a relationship for the “right reasons”

Juggling a full-time hybrid job with a part-time remote gig — and keeping it a secret from your employers — could be quite stressful at times, Olivia said.

Of the 60 to 70 hours she worked between both jobs in a typical week, she said between 20 and 40 were dedicated to her contract gig. She focused on this gig early in the morning, in the evening, on the weekends, or during working hours on the days her full-time employer allowed her to work from home.

She said her contract role had flexible hours and few meetings, which helped make her job juggling possible. Both jobs were in entirely different industries, which made it less likely that either of her employers would uncover her job juggling, she added.

While overemployment has increased Olivia’s work-related stress, it’s reduced her financial stress — something she said has helped her pursue a healthy romantic relationship.

“I know that I’m in the relationship for the right reasons — not financial security — and I don’t feel like I am, or will be, a burden on him,” Olivia said. “We have floated the idea of starting a family, which previously would have been an absolute no from me due to financial constraints and stress.”

There’s likely an expiration date on her overemployment journey

Olivia said she expects the boost overemployment has provided to her finances to be relatively short-lived. That’s because the long working hours can take a toll, and remote job opportunities can be difficult to land.

“I don’t believe that I can maintain this kind of life for more than a couple of years,” she said, adding, “I have no delusions of an early retirement.”

For now, Olivia said she’s trying to last as long as she can. A few months ago, she swapped her hybrid job for a fully remote role that pays more and offers a “considerably better” work-life balance.

While she sometimes wishes she made more money and worked fewer hours, she said she’s sometimes reminded of how far she’s come. For example, a few months ago, she was able to pay over $3,000 for vehicle maintenance expenses without taking on any credit card debt.

“What would have been a tremendous stress a year ago and likely required sacrifices for months was just a minor inconvenience,” she said.

And slowly, she’s let herself enjoy some of the perks of a higher-income life.

“I am moving out of a poverty and survival mindset,” she said, adding, “I feel like I can agree to outings without looking at the menu cost, or can grab something at the store on impulse without having to trade it for something else.”

However, when it comes to homeownership, she remains pessimistic. As long as she lives in her area of California, she’s not sure she’ll ever buy a home.

“To get something even livable that would pass inspections would require me to maintain this level of employment for the foreseeable future and still risk being house-poor,” she said. “It isn’t worth it.”