‘I like not-working better’: A millennial who once made $300,000 secretly juggling jobs tells us why he scaled back

• John, a software engineer, made $300,000 a year, secretly working two remote jobs.
• But after one job loss and a return-to-office push, he’s decided to stop chasing “overemployment.”
• He’s now focusing on a side hustle, savings, and networking to boost his financial security.

Editor’s note: In December 2023 and March 2024, Business Insider wrote about how secretly working multiple jobs had affected the life and finances of John, a millennial software engineer based in California. (John is a pseudonym, but BI has confirmed his identity.) Read more here and here. Now, in a recent interview, John shared how various challenges have posed obstacles to his lifestyle — and how he’s adapted.

Secretly juggling two full-time remote jobs gave John the trifecta he’d desired: a high income, job security, and work-from-home flexibility. But over the past year, a job loss, a return-to-office push, and looming childcare responsibilities have him rethinking how to preserve parts of the lifestyle he’d built.

After joining the ranks of the “overemployed” in 2021, John, a millennial software engineer based in California, earned as much as $300,000 annually working multiple full-time remote roles. The extra income boosted his earnings to over $300,000 a year, allowing him to grow his savings and splurge on things like a roughly $9,000 honeymoon with his wife.

“I figured I’d give it a shot,” John told Business Insider in 2023. “I’d save the extra money to buy a house, or go on a vacation, and fill up my retirement accounts for the aim of perhaps retiring early.”

But about a year ago, one of his two roles — a full-time contract position — ended when the company folded, leaving him with just his W-2 job, which pays more than $150,000 annually.

More recently, John’s employer began encouraging employees to work from the office a few times a month — an informal policy, but one John felt he should respect to stay in good standing with his boss. And perhaps the biggest development: He and his wife are expecting their first child — a life change that will bring its own set of responsibilities.

In response to these developments, John says he’s trying to build a different kind of lifestyle — one that still retains much of the income, job security, and flexibility of his job-juggling years. His new approach rests on three pillars: a side hustle, aggressive saving, and leaning on his professional network.

“I never got back to full-time overemployment,” he told Business Insider in August. “But I’m fortunate to say that I’m not really worried about finances at this moment.” Business Insider has verified his identity, employment, and income, but agreed to use a pseudonym.

John is among the Americans who have secretly juggled multiple remote jobs to boost their income. Over the past three years, Business Insider has interviewed 30 overemployed workers who’ve used their extra earnings to travel the world, buy expensive weight-loss drugs, and pay down student debt. But in recent years, job juggling has become more difficult amid tech layoffs, a white-collar hiring slowdown, and return-to-office mandates. Still, some workers have found ways to hold on to parts of their overemployed lifestyles, even as their work situations evolve.

Contact this reporter via email at [email protected] or Signal at jzinkula.29. Here’s our guide to sharing information securely.

Read more of BI’s stories on overemployed workers:

• A Gen Xer who secretly works 3 full-time remote jobs and makes $344,000 paid off his mortgage and is saving to send his kids to college debt-free
• A millennial made $300,000 secretly working multiple jobs — while tasked with catching others doing the same
• Meet the Americans secretly working multiple remote jobs to afford early retirement — and making up to $300K
• I caught my employee secretly working a second remote job. Here’s why I decided to fire them.

Scaling back meant saving less, not spending less

After losing his contract software engineering role, John updated his résumé and began casually looking for work, but found the job market challenging. He eventually asked a friend if their company was hiring — a conversation that led to him landing a part-time remote software engineering role that pays about $50 an hour, a gig he’s held for over six months.

When he works from home, John juggles both jobs during his roughly eight-hour workday. He expects to earn around $60,000 from the part-time gig this year, bringing his combined income to about $225,000 — down from $300,000 when he was working two full-time jobs. In the first few months of his part-time role, he said he billed about 20 hours a week and worked about 40 hours between his two jobs — compared to as much as 50 hours when he held two full-time roles. John said his main employer knows he has a side gig of some sort, but doesn’t know the specifics of the role — or how many hours he devotes to it.

Given the part-time hours for his second job, John said juggling both roles was manageable. But a few months ago, he chose to reduce his part-time work even more — to between five and 10 hours a week. With a child on the way, he said he wanted to make sure he had enough time to help with childcare responsibilities and reduce the risk of burnout.

“Just in terms of cognitive load and mental stress, I wanted to keep that slack open for taking care of household duties,” he said.

Scaling back his hours has meant adjusting to an even lower income. John still expects to earn about $60,000 from his part-time gig this year, but if he continues at his current pace — at just five to 10 hours a week — his annual earnings from his side gig would drop to around $20,000 next year.

Since he began job-juggling in 2021, John said he’s generally lived off his W-2 income and put most of his contract earnings into savings — estimating that he’s saved over $150,000. He’s managed to stick with that approach, so while his savings have grown more slowly with fewer contract hours, he’s still been able to set money aside.

“Losing that income has caused us to adjust our standard of living a little bit, but it’s really just saving less money,” he said. “It’s not really spending less.”

He’s trading a backup job for a backup plan

John said he hasn’t had to cut back much on spending in part because he was already pretty frugal. During his overemployed years, he didn’t buy a new car, flew economy, and often stayed at 2-to-3-star hotels when he traveled. Splurging on his honeymoon was the exception.

The savings John has accumulated in recent years have helped him feel more financially secure. He said he has a rainy-day fund that could cover about six months of living expenses if he lost his job, along with other savings he could tap in a worst-case scenario.

But John doesn’t expect it to come to that, in part because he feels fairly confident in his job security — he said his company doesn’t have much of a history of layoffs. And if a layoff did happen, he feels pretty good about his job prospects. He said he’s built a strong network over the years and knows several startup founders and hiring managers in his industry who he believes would help him find employment.

“I’m pretty confident that I’d be able to secure another full-time job in pretty short order,” he said.

Returning to the office has made job juggling harder

While John isn’t actively looking for a second full-time job to replace his part-time role, he said he sometimes speaks to recruiters when they reach out to him on LinkedIn or via email. If a role seemed like a good fit — and flexible enough to lend itself to overemployment — he said he’d at least consider juggling two full-time roles again.

But given that he’s now being asked to work from the office a few times a month for his full-time role, John said juggling two full-time jobs would be difficult. One way he used to manage his responsibilities as an overemployed worker was by working on tasks for one job while attending virtual meetings for the other. That wouldn’t be possible in the office.

“It would be really difficult to do overemployment on office days,” he said. “I can’t really take meetings from the office.”

Still, John said his employer’s office policy isn’t very strict, and that he feels comfortable working from home all five days when personal commitments come up. Overall, he’s grateful to still have as much flexibility as he does.

“There’s nothing held against us if we can’t make it into the office,” he said.

While John may not have the same level of income, job security, and work-from-home freedom he once did, he said he believes he’s held onto a fair amount of it. And despite the perks of his former lifestyle, he’s optimistic that his new one — with fewer hours and less stress — will ultimately be the best thing for him and his family.

“As much as I like working, I like not-working better,” he said. “My priority in life will always be my family, and being able to focus on what matters will be great for my well-being, as well as that of my family.”

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