A millennial who made $225,000 secretly working 2 remote jobs shares why he decided to give up overemployment: 'The juice wasn't worth the squeeze' (2024)

Roughly three months later, he was secretly working two full-time remote jobs and earning about $225,000 a year in combined income. He said he used the extra money to make a down payment on a truck, start an Airbnb, and pad his savings.

But earlier this year, after roughly 13 months of being "overemployed," Luke quit his second job. While he considered carrying on, he said five factors were working against him: an upcoming promotion in his first role, a difficult boss, the recent birth of his first child, higher taxes, and a return-to-office mandate.

Over the past year, Business Insider has spoken with more than a dozen job jugglers who used their six-figure earnings to pay off debt, plan for an early retirement, and afford expensive vacations and weight-loss drugs. While some employers may be OK with their workers taking on a second job, doing so without approval could have repercussions if a worker is caught.

While working multiple full-time jobs can be very lucrative, fierce competition for remote roles has made this unattainable for many people. What's more, return-to-office mandates and burnout can make job juggling unsustainable.

Luke shared how he tried to keep both jobs going as long as he could — and why he ultimately decided to give one up.

Juggling both jobs felt manageable and worthwhile — until it didn't

Luke's overemployment journey was a bit of a roller coaster.

Before he found a second job that stuck, he said he started one that only lasted about a week before his employment was terminated. Luke wasn't sure if his job juggling had been exposed or if the company just changed its mind — he never found out.

When Luke started his more successful job juggling stint, it wasn't too difficult to manage both jobs. He said he only worked between 40 and 50 hours a week between the two roles and didn't have much trouble avoiding double-booking his calendars.

But he said the boss at his second job often left him frustrated.

"I hate my boss with a passion," he told Business Insider before he quit.

Over the past year, both work and home responsibilities made job juggling even more difficult. At his primary job, he said an upcoming promotion forced him to take on a bigger workload and put in longer hours. At home, he and his wife welcomed their first kid.

At the same time, the extra income from his second job — which paid about $80,000 a year — wasn't boosting his finances quite as much as he initially expected. That's because it slotted him into an income bracket with higher tax rates.

"Of the money I made from the second job, a third of it, I had to basically hold back just for taxes," he said.

"The juice wasn't worth the squeeze"

Earlier this year, Luke faced perhaps the biggest challenge in his overemployed journey: His primary job was switching its policy from fully remote to hybrid by the middle of 2024 — which would require him to come into the office a few days a week.

For many job jugglers, a return-to-office mandate would be the nail in the coffin — at least for their existing working arrangement. But Luke tried to figure out how to keep both jobs going.

On the days he had to work on-site, he could use his personal office to juggle both jobs without anyone peeking over his shoulder, he said. His main concern was that his employer would notice that someone from a different company was using the internet connection.

However, after weighing the challenges the hybrid policy would present, in addition to the other downsides of job juggling, Luke ultimately decided that "the juice wasn't worth the squeeze." His second job would have to go.

But he didn't immediately hand in his two-week notice. That's because he thought he could get a few easy paychecks first.

Luke said his company typically went through a multi-step process before parting ways with poor-performing employees, so it'd be possible to string out the process for at least a month.

But he soon decided this strategy wasn't worth the extra income either — and called it quits.

"I'm not going to try and juggle both jobs," he said in March. "I thought about it, but with the new baby and a promotion coming, it's just too much."

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 jzinkula@businessinsider.com.