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The “Overemployed”: working two full time remote jobs

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Every few years, it seems some new and emerging trend leaves us bewildered. Years ago, it was the tiny house movement; the act of drastically downsizing your home in an effort to lower your cost of living and impact on the environment. Then, it was digital nomad-life; the act of living on the go and working remotely with no permanent or primary residence at all. Much like the FIRE movement, these trends slowly become sub-cultures and communities where people who participate in them openly share resources and insights to help one another.

Well, just when we thought things couldn’t get more interesting, we stumbled upon another trend that has the potential to redefine how we a new generation manages their careers and income. We’ve all heard of people working multiple jobs to earn more money. Well, a growing number of professionals are secretly working multiple remote full-time jobs. Taking full advantage of the growing acceptance of work-from-home policies and remote work due to the pandemic, folks are using this opportunity as a way to balloon their earning potential.  And much like the other trends we’ve been drawn to, they even have a catchy name. 

They consider themselves “overemployed”.


We’ve found a handful of articles about the overemployed this year. But the very first time we’d heard about it was in the Wall Street Journal. In the article, they profiled a handful of white-collar/knowledge workers to understand why they became overemployed.  And to no one’s surprise, their responses were similar to those that drive people to pursue financial independence.  People are frustrated with corporate workplace culture, the limits placed on their earning potential and the idea of having to work their entire adults lives.

People are frustrated with corporate workplace culture, the limits placed on their earning potential and the idea of having to work their entire adult lives Click To Tweet

Then, more recently, we stumbled upon a video by Bloomberg on Youtube [embedded below] that profiled how it all works in even greater detail. We were completely awe-struck by how people managed their calendars, set up their offices and used specialized equipment to avoid getting caught. Even more interesting were the elaborate lengths they undertook to preserve their anonymity. You’d think they were in a witness protection program or sold illegal drugs for a living but nah…they’re just white collar workers that don’t want their employers to know they have another full-time job.


Our minds were officially blown and rather than leave it alone, we decided to reach out to our subscribers, viewers and followers on social media to see if we knew anyone that was actually doing this. Given many of them are Black, we were curious about what their experiences were like and whether their “overemployed” experience or motivations were different from what we’d seen and heard. Low and behold, we were able to find several people within our own community who were able to share their experiences with us.

So we decided to interview them to learn more about what they’re doing, why they’re doing it and how it’s impacted their financial life. If you’ve ever thought about working multiple remote jobs, consider this blog post a handy little resource. And as an added bonus, we recorded an entire podcast episode [56] about this topic as well.

Altogether, we spoke with three people about their experience working more than one remote job. Here’s what they had to say.


Sam and Irene: Atlanta, Georgia

Ok, lets just get this out of the way. Their real names aren’t Sam and Irene. To protect their identities, we’ve changed their names and those were the first two we could come up with. We’ve known them for a few years now and all we can say is they’re two of the kindest, smartest and hardest-working people we’ve ever met. Like us, they’re married and live in the suburbs of Atlanta.

Both Sam and Irene work in tech with Sam’s emphasis being data management and Irene’s in management consulting. Like many people, when the pandemic hit, they started thinking about their own job security. That, coupled with frustrations with their jobs and aspirations to achieve financial independence, they decided to get scrappy and pursue getting another remote job. Given both their skills are in high demand this wasn’t particularly hard for them to do.

We didn’t get into hard financial details but with one additional remote job they were able to grow their relatively high net income another 40%. With the extra money, they increased their emergency fund, contributions to retirement accounts as well as a taxable brokerage account. The ease in which they were able to do this is largely due to how their roles (as individual contributors) are structured and how efficient they are as workers. But what we found to be most interesting about their motivations wasn’t how much more they could spend or invest; but who they could help.

They’re both first-generation immigrants and their home country has fallen on hard times in recent years . So Sam and Irene routinely find themselves sending money back home to help friends, family and even strangers. Sam shared with us that given the crisis in Ukraine and the reports of Black people being treated poorly while trying to flee the country, he’s regularly sent money to stranded students and practically anyone he’s found is in need on Twitter. In addition to this, his parents are still in his home country and they’ve been wrestling through the process of bringing them to the US.


Lenore: DMV Area

Lenore [also not her real name] is a project manager for a large tech company that produces cloud software. What that tech company doesn’t know is that she’s also a clinical researcher for a big pharmaceutical company. She was willing to share financial details with us about her experience and the results are pretty impressive.

In her first job as a project manager, she was making $108,000. Now, almost four years later, she’s earning $135,000. In her second job as a clinical researcher, she started earning $115,000 and now earns $141,000. So in total, her estimated take home pay is about $276,000. Now, to put this in perspective, we also have to consider that she lives in the DMV area which has a notoriously high cost of living. As a result, salaries are typically higher than they are in smaller, more affordable markets.

When we asked her about her core motivations, Lenore’s responses were similar to the others we’d heard. She’d stumbled upon the FIRE movement, didn’t enjoy the traditional 9-5 work environment and wanted to have more time to enjoy life while she was still young. Considering “my fun is expensive” Lenore says, she chose to take on the additional workload to earn more money than she realistically could have if she’d only had one job.

But she doesn’t burn it all on mimosas at brunches and vacations. With the additional income she invests 10% in the company’s employee stock purchasing plan [ESPP], tithing [another 10%] and the remaining 80% into a taxable brokerage account she set up for her parents. The best part is, her parents don’t know that she’s doing this for them.

What’s also interesting about Lenore is that she’s been doing this for four years now, long before the pandemic made remote work popular. When we asked her how much longer she planned to keep this up, she said

I will continue as long as I can without sacrificing my health or free time. There is a lot of autonomy in the roles as long as you are meeting metrics and timelines. All in all, I see this second job as my version of being married and living on one income

“All in all, I see this second job as my version of being married and living on one income” Click To Tweet


Tip: Columbia, South Carolina

Tip is a Graphic Designer based out of Columbia, SC. First, she worked remotely for a lighting company earning $57,000 a year but after her employer began pushing for employees to return to the office, she resigned. Then, after taking a few months off, she decided to focus on her freelance career which provided her consistent income and much more flexibility. But soon, she found herself back in corporate.

Only this time, she was earning $92,000 in a remote contract position with a biotech company. But, even with the 60% pay increase, she didn’t give up on her freelance work and the clients she secured on retainer. Now, in addition to the full time job, she is able to regularly bring in $3,000 more a month. So together, between her primary job and freelance work, she earns approximately $128,000 a year. A huge leap from her original, $57,000 annual salary.

Her primary focus is to use the extra income to pay off debt, invest and provide financial support to her Mom. In fact, her family was a primary motivator for why she moved back to Columbia, SC. After her Dad passed away, she felt compelled to return home and help her Mom with expenses, especially since she knew she could do it without putting a financial burden on herself. This way “I have more financial flexibility, allowing me to find more opportunities to grow personally and financially” she said. Tip has been pulling double duty for the last nine months. When we asked her how long she planned on doing this, she said “as long as my schedule permits“.


Thoughts on Overemployment

In our book, Cashing Out, one of the chapters we know will get a few people talking is called, The Fifteen Year Career. In it, we tell our own stories of how we were able to walk away from jobs and the stories of a few others who were able to do the same in under fifteen years. But honestly, had we known about this trend of overemployment when we were writing It, we’d have certainly included a section outlining the approach, it’s pros and cons. In a way, it makes us feel like we’re old school!

We’re intimately familiar with side-gigs, real estate investing, living frugally so you can invest more and building a business during off hours. But the thought never occurred to us that we could combine remote jobs and do that to boost our income. In part, this is because the nature of our jobs [mostly in sales and marketing] would’ve made it impossible. We were in the “people” business and while working remotely was allowed, there’s no way we could’ve done it during our traditional working years.

But this recent trend and the growing prevalence of remote work changes everything. And if nothing else, further proves the point we’re making in our book. With focused work, leveraging technology and savvy investing, there’s little reason for qualified professionals to lock themselves into 30, 40 or 50 year careers. And for Black professionals especially, taking control of your finances, career trajectory and earning potential is critical if we [as a community] aim to build multi-generational wealth.

But like all things, there is more to consider here.

First, we can’t help but to see the similarities between these three stories. Notably, and like us, every single one of the people we spoke to are financially supporting their parents. There’s tremendous pride in being able to do this but could have a negative impact on your physical and mental health. Furthermore, we have to question what impact this may have on people’s abilities to nurture healthy interpersonal relationships or start a family. And in case you’re wondering, none of the people we interviewed had children.

Secondly, it’s impossible to ignore the spirit of rebellion in these stories. Everyone we spoke to was “fed up” with workplace culture and the pain a 9-5 forces onto their life. Whether it was issues relating to their racism, sexism, unrealistic expectations placed on them by bad managers, politics, or inflexible work policies, combined— it was enough for them to search for solutions that allow them to walk away from the grind.


While we don’t know how long either of our interviewees will keep this up, here’s what we do know; they’re all earning a $hit load of money and have the opportunity to build multi-generational wealth in an astonishing period of time. But this won’t come easily. Working two remote jobs creates it’s own set of challenges, but if you’re strategic and maybe a little lucky, they may be challenges you can afford to outsource.

Also, if you’re interested in this approach, keep in mind that you don’t have to work two jobs of equal weight or responsibility. If you have a skill that’s in high-demand and only realistically have ten extra hours to work, you may be able to supplement your job with a less-demanding, non-managerial role. This may earn you an additional $50K instead of $75K or $100K but it’s still a huge boost in income that has the potential to improve your quality of life immediately.

The point is, we’re living during a time where many of the old rules to money and careers don’t apply anymore. People are getting scrappy, finding loopholes and make short-term tradeoffs that yield big results. And if the overemployed trend is anything like the others we’ve been drawn to, five years from now it’ll be the norm for a significant segment of the population.





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