How an Overemployed Worker Spends His Money: Travel and Food

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  • A Florida-based Gen Xer made over $300,000 in 2023 secretly working multiple remote tech jobs.  
  • While the extra income has allowed him to travel more, he still feels “far from rich,” he said.
  • He shared how his higher income has impacted his relationships and how he’s spending the money. 

In 2021, Robert was making roughly $180,000 a year from his tech job, but when his workflow slowed, he feared a layoff may be coming soon.

He decided to start looking for another role and eventually found one that paid $190,000 a year, he previously told Business Insider via email. But before he resigned from his current job, he recalled hearing about a former coworker who was making several hundred thousand dollars secretly working two jobs.

After thinking it over, Robert decided to try to juggle both roles at the same time. That choice changed his life.

In 2023, Robert earned over $300,000 across multiple remote roles, according to documents viewed by BI. He said the extra income allowed his partner to quit their job and made it possible for him to take several expensive vacations, including a roughly $20,000 cruise.

The Gen Xer, a Florida resident, is among the “overemployed” Americans who are secretly working multiple remote jobs to boost their incomes. Over the past year, Business Insider has interviewed more than a dozen job jugglers, many of whom are in the IT and tech industries, who’ve used the extra money to pay off debt, save for retirement, and afford weight-loss drugs. While some employers may be fine with their workers having a second job, doing so without company approval could have repercussions if a worker is found out.

For Robert, the income from multiple jobs decision has made it possible for him to travel more. Over the last few years, he estimates he spent between $28,000 and $35,000 in total annual travel expenses. Some of his recent trips included Yellowstone, the Galápagos Islands, and Las Vegas.

“We now spend a lot more time on vacations,” he said. “We spend a lot on travel because life is more about experiences and memories than material things.”

Still, Robert considers himself to be “far from rich,” in part because it takes more than a couple of years with a higher income to ensure financial security in the long term, he said. He experienced several job separations in the past, so he knows his jobs aren’t guaranteed to last. Additionally, he said he made some bad decisions when he was younger that set back his finances.

“We don’t live an extravagant life by any means,” he said.

Robert shared how earning more has impacted his relationships with his partner and family — and how he’s spending the money.

The extra income goes to travel, food, home, and family

Robert said making more money hasn’t changed his relationship with his partner much. But it has been good for his relationships with his family, as it’s made it possible for him to visit them more often.

He said it’s also allowed him to provide some family members with financial support — he estimated that he spends about $5,000 to $6,000 a year helping out relatives. But finding the right balance can be tricky.

“I am careful with that because I know financial help to some actually is a disservice and prevents people from pushing themselves to succeed,” he said.

Aside from family and travel, Robert said he spends most of his money on food and his home.

Food is something he doesn’t typically budget for, but these expenses can add up, particularly when he travels, he said. On a five-day trip earlier this year, he said he spent about $700 on food, including $225 on one meal for himself and two family members. He estimated that in the typical month, he spends between $1,500 to $2,000 on food.

“We eat well,” he said. “I grew up poor with little to no good food and that is something I do not skimp on.”

Robert’s housing expenses include a monthly mortgage payment — he said he has about $380,000 left on his loan balance.

He’s also putting over $100,000 into refurbishing his home, according to documents viewed by BI. He said this money is going toward a new deck with a high-end hot tub, his basement, and an over 1000-square-foot garage, which he said will be used for two vehicles, a gym, and storage. He said he’s taken out loans to fund some of this spending.

Additionally, Robert said he’s bought two vehicles in recent years, — both of which are mostly paid off — and that he tries to put as much money in his 401(k) account as he can.

However, Robert said he’s not satisfied with the state of his finances.

“My partner and I would like to have no debts in five years unless we invest in a vacation home for us and the family,” he said. “We would also like to have $250,000 saved up in six or seven years which is separate from our retirement accounts.”

Are you working multiple remote jobs at the same time and willing to provide details about your pay and schedule? If so, reach out to this reporter at [email protected].

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