Why a millennial gave up on 'overemployment' despite making over $500,000 secretly working multiple jobs


William, a tech worker in Texas, was drawn to the idea of secretly juggling multiple remote jobs to increase his income after learning about the "overemployed" community on Reddit. Before the summer of 2022, he had a corporate customer-facing tech role and also ran a remote consulting business. In June 2022, he left his corporate role and took on two new jobs at large tech companies, while continuing to run his consulting business. By the end of the year, his combined gross earnings from the four roles totaled over $500,000. This substantial increase in income allowed him to pay off outstanding student loans, clear debts, and make significant investments in his ventures.

The additional income was especially valuable as it helped offset roughly $100,000 in losses his business incurred in 2022 due to his investments. It also provided a firmer financial footing during industry layoffs. However, by February 2023, after eight months of overemployment, William resigned from both corporate jobs, feeling burned out.

Before starting the corporate roles, William had numerous job offers, with many offering over $300,000 in total annual compensation. Eventually, he accepted the two corporate roles, keeping his overemployment a secret from everyone outside his family.

His typical weekday involved working on his business from 7 a.m. to 9 a.m., then juggling both corporate jobs from 9 a.m. to 5 p.m., and later focusing on his business again from 5 p.m. to 9 p.m. He claimed to manage the corporate jobs because of his productivity, as both roles rewarded performance more than hours worked. However, the constant focus on work and accumulating household responsibilities began taking its toll, leading to burnout.

During his over-employed stint, William learned that workers should carefully check company policies for explicit prohibitions against having multiple jobs. His experience revealed that it's easier to manage multiple jobs if there's more control over day-to-day responsibilities and schedules. He also learned the importance of blocking off parts of his calendars for both jobs to prevent meeting conflicts.

While he found balancing his work and avoiding suspicion challenging, he ultimately valued the financial benefits of his over employment experience, even considering a return to one of the jobs he left.  

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