How a millennial makes $200,000 working 2 remote jobs at the same time

  • A full-time account manager at a software company has started a second job as a sales representative.
  • He still works 40 hours a week but expects to earn around $40,000 in extra income this year.
  • The money is used to pay off his credit card debt, his wife’s college fees and his retirement savings.

Fayette Woods, 26, says he needs two jobs to meet his financial goals, including paying his wife’s college fees, saving for retirement at 60 and meeting bills for a period of high inflation for four decades.

But Woods works both jobs the same hours, and neither employer knows the other.

“In this economy, you can’t get by on just one income,” Woods said. He asked that his real name and employers remain anonymous for privacy reasons, but his identity is known to Insider.

Woods, who is a full-time account manager at a software company, also sells furniture for a retailer. He said working remotely for both jobs helped him avoid getting caught – and that only became possible during the pandemic.

Working around 40 hours a week – while being paid 60 – Woods expects to see a $40,000 jump in salary this year. He’s on track to earn more than $160,000 at the software company this year, including commission, pay stubs seen by Insider showed.

This has opened up new possibilities for Woods, who has paid off all of his credit card debt since he started working two jobs last November and plans to start his own business with the extra cash.

More and more Americans are finding it necessary to follow a path like Woods’ as the cost of living rises ever higher. In addition to the last year of record inflation, housing, education and health care costs have been rising for decades. And although the Great Resignation has forced companies to raise wages, it is a drop in the ocean after decades of stagnant wages. To cope, some white-collar workers are secretly working two remote jobs, many earning between $200,000 and $600,000 a year, as The Wall Street Journal originally reported.

“It feels like a lot of work, doing two jobs, and the first month is tough because you have to find the balance,” he said. “But once you get through that phase, it just becomes part of your daily life.”

The science of choosing a second job

Woods said he realized his job at the software company didn’t fill a 40-hour week and he could spend time making money elsewhere.

“I don’t have a college degree and I’m only 26, so for me to work two jobs where I make over $150,000 a year is impossible,” Woods said. “I wanted to make more money so I could do more things, so I could invest. I wanted to build my nest egg.”

Woods said there are two factors to consider when choosing a second job. First, make sure that the schedule of tasks required for each job does not overlap. It’s also important that your second job isn’t so much extra work that you burn out.

He said he learned those lessons the hard way with his first attempt at a second job. Last November, he started working part-time at an analytics company in addition to software work, but the analytics company wanted him to do cold calling during times that interfered with his other work.

“I realized that I shouldn’t just seek positions for money,” he said. “I also needed to pursue my happiness.” He said he prefers work-life balance to his current job mix, where he doesn’t have to take work calls after hours.

He also said his system seemed like the best way to cope with rising costs all around him, namely record US rent.

The extra money from his job at the analytics firm meant Woods could clear his credit card debt balance — more than $7,000, Insider confirmed. Before getting his second job, he said, he could only pay interest monthly. With the extra income, he was finally able to tackle the main debt.

A second job also means he and his wife can pay $2,000 rent for a four-bedroom apartment. And having children is something they are more comfortable with now that they have more savings.

Get out of overemployment

Woods said working two jobs came with an adjustment period, but now he’s found a rhythm.

From 7 a.m. to 10 a.m., he works for the software company. From 10 a.m. to 2 p.m., he balances his software work with his calls for the furniture retailer. Then from 2 p.m. to 4 p.m., he again works exclusively for the software company.

Woods said it was manageable because the duties of his job at the retailer matched the duties of his full-time position. He makes five phone calls an hour to sell furniture, and he monitors his hours at the software company. It also helps that he doesn’t have daily meetings.

But that doesn’t mean he hasn’t had close calls.

When Woods juggled the old part-time job at the analytics company, he said, he sometimes had to be in two meetings at the same time, with his camera and microphone off and using two headphones.

Once, one of his bosses tried to call while he was talking to his manager at the other company.

“I could tell I was having technical issues on Zoom,” he said. “If I worked in the office, I couldn’t do that at all.”

‘Swallow your pride’

Woods said it’s important not to be particularly choosy about the prestige of a second job. What is more important is work-life balance and work-work balance, he added.

“My advice is to make sure you set a schedule and stick to it, swallow your pride, and take that extra $15 an hour,” he said.

Woods said his only “biggest resignation regret” while changing jobs was “right after higher pay” when he briefly quit his job at the software company in 2020 to work at JPMorgan. He was fired after six months and returned to the software company, which he said was “a blessing in disguise”.

“Some companies expect a lot from you and look good on paper,” he said. “Instead of quitting a job you love, add a second job,” he advised. His sentiments echo those of many workers who quit their jobs over the past year for better pay, only to eventually quit their new positions as well.

Woods said being overqualified for his retail job makes it easier.

“I have 10 years of sales experience, so I could go get another high-caliber job,” he said. “But a lot more stress comes with one.”

But moonlighting as a furniture salesman does not inspire these feelings in him.

“It’s the equivalent of LeBron James winning a game of 21 at community college — a little work here, but not that much,” he said. “And I’m really getting there.”


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