Technology has made cheating easy. And just as cheaters can easily date multiple people without any partner being the wiser, some workers have figured out how to hold multiple jobs that their employers don’t know about.

Thanks to technology, more and more workers are participating in overemployment, overlapping their job roles without bosses or teams knowing about these other jobs because one or more are remote roles. Some employees justify this duplicitous action as necessary to combat poor wages and the high cost of living.

Cheating on your boss in the virtual workspace: is this the new moonlighting? It’s called overemployment, and it’s becoming more common in our tech-savvy world.

For example, I know of an administrative assistant at a law firm who side-gigs as a physical trainer, and she uses her lunch breaks to train clients via Zoom. This side gig seems reasonable and probably isn’t a deception because it doesn’t affect her primary work. Equally important, there’s no real or perceived conflict of interest since the jobs are very different.

But what happens when employees violate a contract stipulating that they must only work for one organization at a time? And what if an organization finds out its employee is also working for its competitor?

The most likely answer is that the employee would be fired without a second thought, just as one might dump a two-timing partner.

One single mother who works remotely for two firms stated, “It’s not like I enjoy having two jobs, two sets of deadlines, two sets of meetings, sometimes with overlapping schedules, so I have to make up an excuse why I am late for some video meetings. The stress is two-fold. I am constantly worried about being found out. Trust me, I wish I could devote my time to one organization, but unfortunately, I have bills to pay and kids to feed. I used to feel guilty about sneaking behind my bosses’ backs, but why should I? If companies really want allegiance from their staff, they should care more about the wages they pay.”

Five Reasons Employees “Two-time” Employers

1. Financial reasons

Like the aforementioned single mother juggling two jobs simultaneously to make ends meet, many others are doing the same to meet their financial obligations. With high inflation, even single post-secondary graduates with fewer responsibilities need two or more contracts/jobs to live comfortably. Between student loans and escalating housing prices, I suspect that many twenty and thirty-somethings may be deciding to join the virtual workforce with the intention of working for more than one organization.

2. Job uncertainty/instability

Contract, seasonal, and commission-based work is more common than ever, and remote work is comfortable. It’s unsurprising that workers have a sense of unease knowing there is an end to their employment. In this context, it makes sense to simultaneously have two or several contracts as a hedge against one or more positions ending.

3. Advancements in Technology

Since the pandemic, many of us rarely ask others where they physically go to work. The assumption is that many workplaces are now remote or hybrid. Plus, technology allows workers to be in two places simultaneously, leading to the idea that they can also be “working” two jobs simultaneously – without ever needing to ghost either employer.

4. Feeling undervalued and wanting more opportunities for advancement

In previous blogs, I mentioned how employees feel undervalued when repeatedly passed over for promotions. If an employee feels they aren’t being challenged or progressing in their industry, it becomes more likely they may seek a position in another company while still twiddling their thumbs working at the other.

5. Explore a side hustle, hobby or passion while maintaining gainful employment

This is a common trend among people who desire more in their life and their careers. Perhaps an aspiring writer is typing away at her novel while still stuck in a boring Zoom meeting, while an office manager is busily clicking away at an NFT or Bitcoin trade. This allows people to explore their dream jobs while remaining in a lacklustre role that pays the rent or mortgage.

This YouTuber has chronicled his experiences working two full-time remote jobs concurrently. His story about getting caught ends with a fun twist but also serves as a reminder that people know each other within industries. There is also a subreddit on the topic and related threads.

Disclaimer – This blog is for educational purposes only. I do not condone deceptive overemployment or other forms of infidelity.

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