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  • Writer's pictureGary Grewal

The Great Resignation Versus Overemployed: Should You Negotiate More Pay or Ride Two Horses at Once?

If you’re like me, you’ve grown tired of hearing the phrase “The Great Resignation” being tossed around as an excuse for everything from lack of variety of gluten-free donuts at Whole Foods to waiting 45 minutes for your sandwich order.

Surely if you’ve gone out in public or bought anything at all, you’re noticing things are taking longer, there is less variety, email responses take longer to come by, hold times are longer, you name it. I’ve even been hearing about people fuming over having to wait an extra 3 months for their Swedish leather sectional.

So what’s the cause? Well, as with many so-called crises, there are many opinions to this, so much that the catchphrase “No one wants to work” is being slapped on sidewalk signs and stickers.

Unsurprisingly, many workers who have recently quit have cited pay as one of the top reasons for them walking out the door. Working conditions and treatment of managerment was also a top reason. So with all of the stories of people letting their bosses have it, or taping a sign on the door and riding off into the sunset, should you do the same?

Getting a New Job is Easier Than Dating These Days

It’s one thing to do something because something inside of you is speaking out, and another if it’s just because everyone else is doing it. If you have a job you love, are good at, and are fairly compensated, then what would be your motivation for jumping ship?

Sure, the possibility is always there that you could get higher pay, or that you can have better benefits such as more paid time off. But ask yourself, are you jumping laterally, behind or ahead of you with this job change? If it’s intentional, great!

So, if you have been thinking of a new job, have acquired some new skills, or just want something that aligns better with your interests and outside-of-work obligations, then start poking around job postings or get in touch with recruiters.

Today, I’ve found it’s easier than ever to find companies that are hiring. If you’ve been on LinkedIn the last several months, you’ve surely seen the “We’re Hiring!” Banners and shared posts fill up your feed. I’ve even gotten direct messages from connections I haven’t spoken to in years because they think I might enjoy a job. (The power of who you know, ya know?)

If you’re not someone who uses LinkedIn, perhaps if you’re a heavy machinery operator or an electrician, then being out and about you’ll also see physical banners, billboards, and neon signs. I’ve even seen YouTube ads featuring a solar installation company that wants to hire.

Riding Two Horses or Jumping Between Moving Cars?

Now I want to bring up a crazy idea I started hearing about a few weeks ago. People working TWO jobs, not just one full-time job. Given they are usually remote workers, who work in project development or technology industries, some savvy workers have found it possible to balance the workload, and overlapping virtual meetings, of two full-time jobs.

If you’re like me and graduated into the Great Recession, you probably witnessed the emergence of the term “underemployed'' becoming more popular. It was referencing people who were working jobs they were overqualified for.

For example, many millennials who graduated about 10 years ago were having trouble finding jobs, especially for majors that didn’t easily translate into high-paying jobs (shaking my fist at you computer science majors!).

Baristas, line cooks, retail clerks, and receptionists back then were often walking around with bachelor’s degrees. There was even an MTV series called “Underemployed”. That’s when you know it’s ingrained into our culture at the time!

So now that we’ve touched on Underemployed, here is what handling two full-time jobs is. Yep, you guessed it: Overemployed. There is even a website now,

At first, when I read about it, I thought how is that even possible? Even if you could skate past the terms of your offer letter and avoid the patrol of HR/compliance, how do you even manage two full-time jobs? I will tell you I am someone who absolutely loves my day job and wouldn’t risk it by taking on another.

Even if I could though, I have no idea how I would balance both and have the mental energy to do them both well.

“Sorry, I can’t take your call right now, I have an HVAC tech in my office.”

What I’ve found, is these people working two jobs are commonly in tech, work by themselves, and are often in project-based roles. They have mastered the art of balancing Zoom calls, impromptu chats/messages, and being “available”.

I was amazed when I read some of the stories on people actually doing this.

And get this. Not only are these usually already high-paying positions, but many tech jobs also come with the coveted “equity compensation” package. This basically translates into RSUs, which are Restricted Stock Units, meaning the employee receives stock in lieu of cash at certain intervals or as bonuses.

I’ve had friends who’ve worked for some of the big public tech companies, and one of them received RSUs in his first year of work that were worth more than a YEAR’S worth of salary. So, you can imagine how many mouths water at wanting to try this and stick it to our capitalistic society.

According to, it’s also legal to work two or more jobs.

And get this. Some people are one-upping their peers and working not two, but THREE full-time jobs. Yes, you read that right. How they do that and sleep, let alone have a life is beyond me. But hey, more power to them!

Ooh this is exciting! I can get TWO full-time salaries and get away with it?

So, should you stay where you are, jump ship to a higher salary, or try your hand at this new overmployed trend?

The way I would approach this is by looking at your goals and values. Your North Star. Are you at a point in your life where you enjoy what you do and feel fulfilled? Then maybe approaching your employer while armed with your specific accomplishments and talking about a raise might be a good idea.

If you feel you’ve been underpaid for some time, have had to pick up the slack for colleagues, getting more added to your plate with no recognition, then it might be time to test the waters or take up those in your network for the favor of an introduction. Even if you land an offer, your employer might recognize they can’t afford to lose you and bump up your pay.

Take a pause if this happens. This doesn’t always mean you are undervalued if they try to counter an offer and didn’t give you a raise before. It could be a number of things. So if you like the culture and your colleagues and just feel overworked, it might make sense to stay before you decide to quit.

Otherwise, you know yourself better than anyone, so if you’re working a thankless job, now is a better time than ever to get paid what you’re worth, while also taking a step up in your career or gaining new skills. You don’t even have to bug your connections, just start responding to or messaging previous recruiter contacts. Discuss with them what salaries they have been placing candidates into for the positions you are interested in.

Lastly, if you are considering working two full-time jobs, ask yourself this question: Can I do both of these positions with integrity, producing the same value as if I just worked one of them? If your quality of work declines and your coworkers have to pick up the slack, then it might not be such a good idea.

Ethics are important in life too, and if your cover is blown, you might burn bridges that could hurt your career prospects if you get fired. Plus, how would even explain to a new employer where you worked previously? If you just say you worked for one employer, yet the background check reveals something different, how would you explain that?

I definitely think it’s an interesting idea that has emerged. Some of those who are working two jobs have hired virtual assistants and optimized their workspace in a way that they can switch tasks between their two jobs easily. It’s rather interesting to hear about people dropping off conference calls at one job, to take a call from their boss at another job. I guess that’s one way to add suspense to your life!

If you’re a “live-on-the-edge type of person”, then more power to you. Otherwise, take some time to think mindfully, create a journal entry, and talk to friends/mentors. You’d be surprised at the clarity that surfaces when you just think about what you want your life to look like.

At the end of the day, doing what’s right, getting paid what you’re worth, and having the time to enjoy the present might just be the right choice for you!


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