For a few years, John, a California-based software engineer, lived what many white-collar workers only dream about. By secretly juggling two full-time remote jobs, he pushed his annual earnings past $300,000, saving aggressively while enjoying the perks of remote work. But a series of changes — a job loss, shifting office policies, and impending fatherhood — forced him to scale back and rethink what success really means.
The Rise of Overemployment
In 2021, John joined the ranks of the so-called “overemployed” — professionals who hold multiple full-time remote jobs simultaneously. For him, it was an experiment in financial freedom: he boosted his savings, filled his retirement accounts, and even splurged on a $9,000 honeymoon.
“I figured I’d give it a shot,” John explained. “The extra income gave me peace of mind, and I wanted to set up a strong financial base for the future.”
At his peak, John’s combined roles earned him more than $300,000 annually. But by 2023, cracks began to show. One of his contract jobs disappeared when the company folded, cutting his income nearly in half. Soon after, his main employer began nudging staff back into the office, complicating the remote flexibility that had made job juggling possible.
Scaling Back With Purpose
Today, John earns around $225,000 a year — down from his overemployed peak but still strong by industry standards. He now works one full-time job alongside a part-time remote role that pays about $50 an hour. For months, he billed up to 20 hours a week at his side gig, but recently cut back to five to 10 hours to prepare for his most important new responsibility: becoming a father.
“Just in terms of cognitive load and mental stress, I wanted to keep slack open for childcare and household duties,” he said.
Scaling back hasn’t meant cutting spending dramatically. Instead, John’s family lives primarily on his W-2 salary while his side income goes into savings. He estimates he has built more than $150,000 in reserves, including an emergency fund that could cover six months of expenses.
Trading a Backup Job for a Backup Plan
For John, overemployment was partly about having a safety net. But now, he says he relies more on professional networking and financial planning than holding down multiple jobs.
He describes himself as frugal — flying economy, driving older cars, and staying at modest hotels. That restraint, coupled with savings from his peak earning years, has given him confidence. “I’m pretty confident I could secure another job quickly if I needed to,” he said, pointing to connections with startup founders and hiring managers.
Why Overemployment Is Getting Harder
John admits that he sometimes considers returning to two full-time roles, especially when recruiters approach him. But the return-to-office push makes that increasingly impractical.
Working from the office even a few days a month makes it hard to juggle competing schedules. “It would be really difficult to do overemployment on office days,” John explained. “I can’t take meetings for one job while sitting at another office.”
He still enjoys flexibility, noting that his company doesn’t penalize employees for missing office days due to personal obligations. But the days of quietly managing two demanding roles in parallel seem to be behind him.
Redefining Success Around Family
Despite the loss of income, John is optimistic. With fewer hours and less stress, he sees this transition as the start of a healthier, more fulfilling lifestyle.
“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 theirs.”
John’s story reflects a broader reality: overemployment may be fading as layoffs, stricter office mandates, and family responsibilities reshape the workforce. But for him, trading $300,000 for peace of mind and family time feels like a win.
