Editor’s note: In June 2024, Business Insider profiled a supply-chain professional living in Wisconsin, referred to under the pseudonym “Lisa,” who had been discreetly maintaining more than one full-time position at once. Although the name is fictional, her identity has been verified. At that time, readers were introduced to the extraordinary story of how she covertly undertook dual employment arrangements, dramatically reshaping her family’s financial circumstances. In a subsequent interview, Lisa reflected on the profound adaptations she has made since choosing to return to a single job, describing the ways she has preserved a lifestyle similar to the one afforded by her earlier strategy.
For Lisa and her household, simultaneously holding down two full-time roles was nothing short of revolutionary. That unconventional period of her professional life has concluded, yet its influence remains powerfully felt, as she continues striving to sustain many of the benefits it provided. By 2020, Lisa had been earning approximately $110,000 annually working remotely for a corporate manufacturer when she received an enticing offer: a hybrid role paying roughly $150,000. After sober discussions with her husband, she decided upon an audacious and unorthodox solution—accept the new position without relinquishing the older one.
In practice, this meant enduring 18 strenuous months of double employment. Throughout 2021, she accumulated close to a quarter of a million dollars, balancing both positions at an average workload of 40 to 50 hours per week. Complications arose on the days she was required to appear at the office for the hybrid role. Her workaround was both pragmatic and daring: she carried two laptops—virtually indistinguishable from one another—and rotated between them in a cubicle or private office, skillfully juggling competing sets of responsibilities without arousing suspicion.
This experiment in overemployment yielded profound consequences for her family. The augmented salary ensured that she and her husband could confidently plan for the educational futures of their three children. It also created space for her husband to step back from his own career for a period, dedicating himself to childcare at a time when their family most needed his presence. As Lisa explained in a 2023 conversation with Business Insider, the financial cushion provided by her temporary double life would have been unimaginable without such a daring move.
Nevertheless, the strategy eventually became unsustainable. The pandemic era’s flexible work arrangements gave way to revived expectations for in-office attendance, while Lisa herself grew weary from chronic exhaustion. By 2022, recognizing the toll, she relinquished her dual-income arrangement and accepted a supply-chain manager position with hybrid flexibility and annual compensation of $175,000. Though more manageable day to day, the adjustment signaled a noticeable decline from her brief $250,000 peak. Two years later, a new challenge emerged: her company introduced a mandatory five-day office policy, threatening to undo the balance she had delicately maintained since leaving overemployment behind.
Yet in the same way she had once maneuvered into two jobs simultaneously, Lisa displayed resilience in manufacturing new solutions. Her first course of action was to explore ways of discreetly softening or resisting the rigid office requirement. That approach mirrors a broader phenomenon across corporate America: so-called “overemployed” workers who once secretly doubled their incomes, and who today continue to search for ways to retain pieces of the autonomy, security, and freedom they once achieved. Business Insider has documented multiple examples—individuals channeling extra income into university tuition, exotic vacations, and even costly medical treatments. However, the enclosures of the labor market—slowing white-collar hiring and widespread return-to-office mandates—have made such experiments increasingly difficult.
Lisa’s own compromise took shape gradually. After transitioning down to one position in 2022, her employer initially recommended office time but did not impose it, largely because pandemic-related health concerns remained prevalent. For a period, she commuted just once weekly, clocking over an hour each way, a rhythm her supervisor readily approved. Slowly, however, expectations ratcheted upward until late 2023, when a corporate decree insisted upon full five-day presence. Rather than immediately resign, Lisa tactfully approached her manager. Official policy permitted workers to request one remote day per week, if endorsed by a higher-level executive. While her boss was prepared to approve such a request, the ensuing “off the record” dialogue between them proved far more consequential: Lisa explained her long commute and childcare commitments, and her manager privately assured her that strict compliance would not be enforced. Instead, she was asked to appear consistently for critical meetings and to maintain a physical office presence several days weekly.
The unwritten arrangement has endured. Lisa now spends roughly three days in the office, handling significant parts of her role through virtual meetings that make full-time attendance unnecessary. As she explained, she does not openly advertise this flexibility but senses a shared understanding within her working group that productivity, not presence, is paramount. Still, she harbors concern that formal monitoring mechanisms may someday be introduced, potentially measuring badge swipes or hours logged inside the building. Should scrutiny intensify, she fears she could become an easy target for downsizing.
Meanwhile, rebalancing domestic life has required her husband once again to take center stage in childcare. Their youngest child not yet ten, his partial reentry into the workforce has been deliberately modest. By working part-time from home, he manages drop-offs and pickups, filling the gaps once handled by outside programs. Financially, the family has weathered the shift thanks to three principal factors: his part-time rate pays more per hour than his previous full-time job, Lisa’s salary has steadily climbed from $175,000 to nearly $195,000 over three years, and the cushion generated from her time juggling two jobs continues to buffer them from any strain. As she candidly acknowledged, without that earlier chapter of simultaneous employment, their finances today would not be nearly as secure.
Still, Lisa seeks a role even better aligned with her evolving needs. Over the past year, she has submitted applications widely, aiming for a managerial position that rewards experience with competitive pay yet involves either shorter commuting times, more permissive office attendance requirements, or both. An especially tempting opportunity with a 15-minute commute ultimately offered barely half her current salary, forcing her to decline. The reality she now faces is sobering: while she has proven her capability at higher levels of responsibility, upper management opportunities that combine compensation, flexibility, and reasonable proximity to home are exceedingly rare. Her search therefore continues—careful, pragmatic, but underscored by the determination of someone unwilling to forfeit the autonomy and stability she once carved out of unconventional choices.
Sourse: https://www.businessinsider.com/overemployed-mom-gave-up-250k-income-avoiding-rto-policy-2025-9
