The Double-Dipping IT Pro Earning $300,00 a Year Still Doesn’t Feel Rich

Samantha Miller

Using two remote jobs surreptitiously for over two years, Nicholas Flemming, an IT specialist from California, has been earning an amazing $300,000 per year. The ‘overemployment’ has essentially doubled Flemming’s wage, but he still doesn’t feel wealthy, he told Business Insider.

Opening Up About His Experience “Double Dipping”

Flemming discussed his remote work arrangement in an exclusive interview, saying that he thinks one of his managers is probably aware that he has two full-time jobs but has decided not to bring it up.

“He doesn’t bring it up or doesn’t care if I finish my work or not,” Flemming disclosed.

The Genesis of a Dual-Income Lifestyle

According to Flemming, he took the question from a former boss about whether he was seeking for a new job in 2021 as a chance to try his hand at working two jobs at once.

His rationale for trying it out was that he had considered both his present and future workloads and decided to give it a go. “With the additional funds, I would put them toward a down payment on a house, a dream vacation, or even early retirement.”

After two years and more than $150,000 in savings, Flemming revealed that his lifestyle hasn’t changed much despite his increased income. When he travels, he continues to use the same automobile, fly economy class, and stay in average hotels.

The Elusive Goal of Homeownership

“I wish I could say it made me rich, and don’t get me wrong, I’m certainly not hurting for money,” Flemming asserted. “However, the promise of owning a home remains elusive.”

He tried to juggle three jobs at once for a short while on two separate times over the last two years, but ultimately decided it was too much.

The inability to juggle three tasks at once became apparent to him, and he confessed as much.

The Delicate Balancing Act

Flemming attributed his success in juggling two full-time jobs for more than two years to a combination of chance and hard work.

Thankfully, he said, the times of his daily stand-up meetings at both companies don’t conflict, and he’s become very good at juggling two jobs at once. Flemming also noted that the experience and training he receives from one job might greatly improve his performance in the other.

A normal week for Flemming consists of about 40 hours of labor, which is the equivalent of one full-time job, because he consistently works ahead of deadlines and maintains a continuous focus.

The Great Overemployment Migration

Nicholas Flemming’s narrative is part of a rising pattern, albeit it was once unusual. More professionals are covertly juggling numerous tasks at once as remote work becomes the norm for many office occupations post-pandemic.

More than 230,000 people have joined new Reddit communities specifically for the purpose of talking about how to deal with overemployment. Having excellent time management skills and the ability to compartmentalize tasks is essential for the long-term success of those who work numerous jobs.

It also relies heavily on having empathetic supervisors that prioritize production over conformity to a standard of eight hours of nonstop work every day. Integrating productive multitasking into meetings can be psychologically demanding in the long run.

Therefore, professionals who are interested in trying to replicate Flemming’s risky work arrangement should think long and hard about all of the pros and cons before making the leap.

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Samantha Miller is a business and finance journalist with over 10 years of experience covering the latest news and trends shaping the corporate landscape. She began her career at The Wall Street Journal, where she reported on major companies and industry developments. Now, Samantha serve as a senior business writer for, profiling influential executives and providing in-depth analysis on business and financial topics.
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