A millennial worked 2 remote jobs so he could retire at 50 but said overemployment isn't worth the stress (2024)

But by the time Adrian's contract for his second job came to an end in March, a big part of him was relieved, he said. He has little desire to be overemployed again.

"I did make a lot more money than I've ever made before, I think it was a smart idea, and it was kind of fun to tell friends about — but life is better now," said Adrian. His identity is known to BI, but he asked to use a pseudonym because of his fear of professional repercussions.

Adrian is among the Americans who have worked multiple jobs — often in secret — to boost their incomes. BI has interviewed roughly 20 of these job jugglers, many of whom work in the IT and tech industries and use the extra money to pay off student debt, save for retirement, and afford vacations and weight-loss drugs. While some companies may be OK with their workers having a second job, doing so without approval could have negative repercussions.

Recently, however, intense competition for remote roles, return-to-office mandates, and burnout have made the overemployment lifestyle unsustainable.

Adrian shared how and why he first became overemployed, his top advice for making it work, and why he's happy to be back to only one job.

Retirement fears led to overemployment

While some Americans are struggling to save for retirement, Adrian is among those who have taken unique earnings and savings measures to retire early.

Last year, when a recruiter messaged him on LinkedIn about a remote, full-time, contract role, he decided to hear them out.

As he went through the interview process, Adrian realized he might be able to balance both roles. He asked for the highest end of the new job's pay range: $70 an hour.

"If I was going to take something on the side I wanted to be sure it would be worth it," he said.

A few years ago, Adrian would never have made a career decision that was so focused on maximizing his income.

He always believed, "If you love your job, you'll never work a day in your life." He never worried much about his financial future or how much money he was making. It's this philosophy that led him to pursue an "amazingly enjoyable" job — one in an entirely different industry than his current role — that he said paid less than $40,000 a year.

"I didn't really care about making money because I never really thought about retirement," he said. "I just kind of assumed that you work until you're old, then you retire, and it somehow just works out."

But a few years ago, Adrian said he experienced a personal "transformation" that led him to begin prioritizing his financial health and future.

"I would never actually be able to retire by working my old job," he said. "But I never really thought about that, and I did love the life I was living."

He started by looking for a different career path. He went to graduate school, and after a roughly yearlong job search that nearly exhausted his savings, he landed the job he still has now.

Next, he started saving whatever money he could. He and his wife took up house and pet-sitting for a year, which he said allowed him to avoid paying rent as they bounced from home to home every month or so. He also began maxing out his 401(k) and Roth IRA, investing in low-cost index funds, and trying to live in low-cost-of-living areas while keeping his "high-cost-of-living area salaries."

When the opportunity to work multiple jobs came last year, it was just another way he could improve his finances.

What to look for in a second job — and why he's happy to no longer be overemployed

Adrian said that his second employer knew he had a primary job but "didn't care," in part because they were happy with the quality of his work. He never told his primary employer that he took on a second gig, but he doesn't think they would have cared either because he was a "top performer."

Adrian said that before taking on a second job, one should be "very comfortable" with one's main role.

"You need to be comfortable enough with your first job that you feel like you actually have extra time to accomplish other work," he said. He added that it's helpful if both jobs are flexible, independent, and don't have many meetings.

It's also important to make sure you're prepared to have your personal life impacted by your extra workload, he said. This is perhaps the biggest part of job juggling he wasn't fully prepared for — and why he hasn't looked to replace his second job ever since his contract came to an end in March.

While his workload varied, Adrian said he often worked more than 40 hours a week across the two jobs, including on some evenings and weekends. It was manageable, but it began to take a toll.

"Too stressful, too much time away from my partner, can't get outside or go to yoga — not worth it," he said of his overemployment. "I made a bunch of money this past year, but my goals for 2024 are not to maximize my income."

Instead, Adrian said he wants to prioritize his health, social ties, his partner, and "having fun." While he's still much more focused on his finances than he used to be, he said working a second job eventually proved to be a bridge too far.

Even without the extra income coming in, Adrian said he's still in the position to potentially retire before age 50. While he wouldn't rule out pursuing a second job again someday, he said the workload would have to be quite low. For now, he's happy to just have one job again.

"The reduction in stress and time commitments is well worth it," he said.

Are you working multiple remote jobs at the same time and willing to provide details about your pay and schedule? Are you a manager who has experience with overemployed employees? If so, reach out to this reporter at jzinkula@businessinsider.com.