Overemployment: How Remote Workers Take on 2+ Jobs (and 2+ Salaries)

Polly has a secret.

Polly is cheating on her job with three other jobs.

She is taking home four paychecks–all without telling any of her four bosses.

This is overemployment.

I've seen people take on anywhere between four to eight jobs.

Screenshot from Overemployed discord.

I've seen people earn thirty thousand dollars a month through overemployment.

Overemployment is not for everyone. It's not easy, because you're doing two jobs. Sometimes it can feel a little shady. But if you can handle the work and you’re not afraid of a white lie, overemployment can be a workable proposition.

Long-time readers can predict how interesting this was to me since I’m a firm believer in owning your own time. I’ve written before about cheating on your job with your side hustle, and so I was fascinated to get the chance to learn more about cheating on your job with your other job.

I think it's a trend that's going to continue to grow. We are in the exact right set of circumstances for it. It's a really exciting time to be in the workforce working remotely with white-collar skills.

Prefer to watch? You can catch the video here:

My overemployed sources

For this article, I spoke to two very cool people. First, I spoke with Polly, the aforementioned job cheater who's working four jobs. I have 100% anonymized her because she doesn't want her four bosses to figure out what she's doing.

I also had the chance to speak with a man called Zach Wade, the founder/CEO of Wade Marketing. He calls it job stacking and says that the goal is to stack as many full-time positions as you can to essentially increase your personal income–more so than it ever could be if you know you were just working in a standard full-time job.

I met Zach a couple of months ago when I was looking at remote work online. I saw this advertisement on We Work Remotely for Wade Marketing’s Independent Partnership Program saying, “Hey, if you want to learn about job stacking and you want some tools some resources to get going, let's talk.”

I contacted him, he put me in touch with Polly, and this article was born.

How does overemployment work?

Step one works a little bit like this: Say you're Polly. You're working a job and you don't love it. Your boss is a little fickle, and you're worried you might get laid off. At the same time, you've got a growing family. You want to start saving money to move out of your small rental and you want to buy a house.

Maybe you think to yourself: I'm not actually spending 40 hours a week on my job. I may spend 20, maybe 25. And you’re not the exception. One U.K. study reported that office employees estimate they spend an average of fewer than three hours per day doing work–that’s just 15h per week.

This is the reality of a lot of white-collar work. I've experienced this, and I'm sure some of you have as well. Due to the rise in productivity but the stagnation of wages, you're earning the same wage for a job that takes you half the time to do.

Zach was empowered to take on a second role when he realized, as a digital marketer, it took him two hours a week to keep the automated systems running after he had set everything up.

And personally, this was certainly true for me when I started working as an account manager. I was very good at my job, I was smashing every single KPI that I had, and it only took me 20 hours to do that. That's actually what let me start my side hustle.

Step two is to get a second job. So you apply for the second job while you're still at your first job–and here's the crucial part–when you get the acceptance letter, you don't quit the first job. You just take on the second job and keep working.

I have seen people work up to eight jobs on the over-employment subreddit. Some people are taking home thirty thousand dollars a month in wages from their eight jobs.

Zach says that for partners in his IPP, the max they say is $32k. “We don't want it to seem too good to be true, even though we know it's possible… essentially most of the job roles that we teach our partners to go after are between $50k to $90k.”

If you’re like Polly, you now have two jobs. Maybe you find that you have a little bit of extra time and you can maybe even take on a third or a fourth. And suddenly you’ve gone from $60k a year to nearly a quarter of a million, on the conservative side.

Step three is to keep it up. You stay on top of Slack. You stay on top of the emails. You stay on top of Teams. You stay on top of meetings. And you take home the salaries.

That is how overemployment works.

Benefits of overemployment

I know what you’re thinking: it’s the money.

Reader, it’s more than just the money. Money is a huge thing, it's a really good reason

to become overemployed. But the benefits of overemployment come down to more than just the cash.

Let’s break it down.

Quick upskilling/development

Job stacking is great because you're working in so many different companies at once. All companies operate very differently, so you learn so much more and you do so much quicker than you would if you were just doing a single standard job. You’ll pick up multiple tech stacks, systems, and get more hands-on rep than you would at one job. Depending on what industries you tackle, you may be learning brand-new skills altogether.
For example, when I was working as an account manager. As I mentioned, I had a lot of downtime. I was not challenged and I wanted to do something more with my time. Obviously, I knew my boss wouldn't love it if I just packed up and headed home at one every day because I'd done my work.

Then what was I to do with my afternoon? I used this time to start building my blog. I learned entrepreneurship, writing, YouTube, social media, and so much more. This was really rewarding to me. It was so fun and so satisfying – it meant that I could do work that paid the bills, but I could also learn skills that would let me build my business on the side.

Creative fulfillment

Polly found the same thing: her first job wasn't very rewarding and she had a lot of time. Her second job was a little better, so she took on a few more as she found the time. She's doing four jobs today, so she’s gone well past “unchallenged” and is fully into the “ambitious fulfillment” zone, but she’s making it work.

*Screenshot from the overemployed subreddit*

Like a lot of people, I like to work. I like to do new and interesting things with my time. I don't like to be bored, or to be in perpetual pointless meetings. For a lot of people who are overemployed, that's a huge benefit. These people are intelligent. They're independent. They're ambitious. And they’re deeply understimulating at a single desk job. They're not meant to sit around going to pointless meetings at 3 P.M in the afternoon.

Ideological fulfillment

The third benefit is more of an ideological one. As I said, I think this belief that you owe your boss your time is a little bit of an outdated one. Productivity has skyrocketed over the past couple of decades, but wages have stagnated.

You are getting way more done, but not being rewarded for it. To me, it's important to feel rewarded and compensated for the work that you're providing. By getting a second job or taking on a side hustle, you get some ownership of that time back.

I mean it's a little dodgy because you're secretly doing a second job and not telling either of your bosses but ideologically it's very satisfying. You have control over your time again. You are the one who's making money with that extra time. You are choosing what you do with your extra time and your and your extra intellectual capacity. That's very empowering.

Job security

This is very topical! Workers are getting laid off left right and center, sometimes for no reason at all other than to satisfy the owner’s megalomaniatic desire to control the company. It is often done cruelly. It is often done illegally. Companies will simply take the slap on the wrist and do it again next time they feel they’re entitled to waste your time.

Here in the States, especially, there’s this concept called at-will employment. This means

your boss can fire you at a moment's notice. That super sucks because I know a lot of people who have been fired find out on the day. They have an hour to clear out their stuff. Then you're at home, wondering what to do. If you don't have a savings cushion, you're kind of SOL.

(Let’s not even get into the healthcare mess, as American citizens have the unique privilege of having their healthcare tied to their employer’s whims in a way nationalized health care would address.)

And your boss, crucially, does not care. They will do this anyway. If it’s better for their bottom line, they will drop you.

(#NotAllBosses)

That’s fine (well, it’s not fine, but whatever). Companies don’t feel like they don’t owe you anything. Now it’s time to realize that you don’t owe them anything either. You both fulfill the terms of your employment contract and you’re done.

I think a lot of the older generation likes to treat their employer like this kind of almighty God that pays their bills. But the employer doesn't see you like that. Most employers just see you as a literal cog in the machine.

Having a second job and being overemployed means that you have not just money, not just additional fulfillment, not just ideological satisfaction. It also means you have a bit of a safety net against markets you don’t control and erratic employer whims.

This was a big motivator for Zach to become overemployed. When I spoke with him, he underlined that when you have other jobs, you feel a lot more secure. If a job isn't working out, if you don't like it, if you're being micromanaged, or if you don't like the manager – you could just quit. You have options.

Downsides of overemployment

We've talked about all the great stuff: the money, the security, the ideological satisfaction.

Now you're wondering: well, what's the downside? Why doesn't everybody have ten thousand jobs? Well, of course, there are cons to overemployment.

Time management

Polly said this was her biggest challenge: suddenly she had conflicting meetings. Suddenly

she had people demanding work that needed to be done the next day for both jobs. She had people sending her Slack messages at all hours. She had to appear to be online at all times for both jobs – which meant that sometimes she'd be caught a little off guard by a surprise message or assignment she’d missed.

That's tough. That is a hard thing to do.

How do you manage that? Well, Polly told me that one of the ways that she does this is sometimes she just goes to both meetings at the same time! This doesn't work for one-on-ones but I know all of us have been in very long pointless meetings. So for those meetings, Polly feels comfortable just putting her screen off and attending both meetings at the same time.

(Note: this wouldn’t be possible if employers didn’t schedule so many pointless meetings!)

Zach counsels communication instead. “It doesn't happen as often as you think. But if it does, what we say is skip the meeting that you did last. So if Job 1 and Job 2 often have conflicting meeting times, alternate skipping them. In addition, always have a couple of excuses handy, like you needed to take a mental health hour, or had a doctor’s appointment.”

He found that the tolerance for shenanigans was higher than expected at one of his overemployment jobs. He tested skipping multiple meetings in a row, first with excuses and then without any. Ultimately he quit the job because he felt bad, but there was no pushback at all.

Moral quandaries

I found this downside to be the case at my first job. I loved it, I enjoyed the work – it just wasn't quite enough for me. When I started blogging on the side, even though I knew I was still performing my job to all the capabilities that I could manage, I felt a little shady. I felt like I was somehow cheating or robbing my employer of my time. Now I've come to believe that I own my own time, as long as the work is getting done at the job that you're responsible for.

Zach’s philosophy was similar. “As long as you're doing a good job and helping that company grow, as long as you're putting in the work to make that company a more profitable place, as long as you're showing up and communicating um and collaborating with your co-workers and you know being a good teammate, there's no reason why you can't do that same thing at another job.”

But at the time, I still felt like I was cheating. I think a lot of people who are maybe of a more traditional mindset, or maybe who have a slightly different set of ethics, it can feel a little crappy to be cheating on your employer this way with a second or third, fourth, or however many jobs you have.

Especially if you have a close relationship with your employer, and especially if you have a great job, sometimes job stacking might not be the right choice because it just doesn't feel right. That's a valid reason. If overemployment doesn't jive with you, if that's not your jam, don't do it.

Keeping overemployment a secret

Many overemployed folks don't like to share their overemployment status with friends or family. This can cause hardship! You might think your family might just not get it, or they might think that it's too risky, or they might judge you negatively for it.

Honestly, I think if you’re keeping secrets from friends and family, that's never a good look. It's always hard to manage that. This is the biggest issue for me: getting this extra money should not come at the cost of undermining your existing relationships with the people who matter.

I know over on the overemployment subreddit, Rule number one is “We don't talk about Overemployment,” but I disagree with this. I think you should have the ability to talk to your loved ones about what you're doing. If you can't do that, do you genuinely feel like you can't be honest with them? Then overemployment might not be the right option for you.

Is overemployment legal?

Quick disclaimer: I am not a lawyer. This is not legal advice! This is just what I found through my internet research.

The biggest question I had when I ran into the concept was: “Is overemployment legal?”

As long as there is no language in your contract when that bans it, you should be in the clear. Some contracts have a non-compete clause. Others specify explicitly that you can't take on more than one job, or you can't subcontract out work.

Definitely make sure to read your contract thoroughly. If you have to, hire a lawyer if you're really in doubt. But for the most part, most contracts don't include that language, so have a look and make sure that it's the right opportunity.

As a concept, it’s legal. Nobody's going to arrest you for being overemployed (today). You might get caught, and then you might be fired, but as I explained above, you can be fired at any time for any reason, so keep that in mind.

How to become overemployed

I have three stories I want to share. The first is my own – I'm including overemployed as doing my blog as well as my job.

I became overemployed because I was bored. I was working at my current job and I noticed I had a huge amount of bandwidth. I had so much time and I was bored out of my gourd. So I took on the second “job” – this blog.

In theory, if I still had additional bandwidth at that point, and I still wanted to earn more money, I could have taken on a third.

Route number two is what Zach did. He was first working at a digital marketing agency before becoming overemployed. “It varies in terms of client responsibilities, but for most agencies, you're looking at handling anywhere from ten to 30 clients at a time. Typically, you're earning anywhere from $40k to $65k at the max. My employer gave me a set of clients, then a month went, and they’d be like, ‘Hey! Great job with those ten clients. Here's another client.’ Over the course of a year and a half I got 32 client accounts, but still making the same $62k.”

He was already overemployed on behalf of his agency – just with none of the benefits and all the extra work. He was effectively the full-time digital media marketer for 30+ companies and still earned the same amount as when he had 10 clients.

When he realized that, he started looking at job boards where he would be doing in-house marketing for a single client. He interviewed with an SEO agency and got a full-time job doing lead generation for that one company. They gave him a salary of $48k.

“I was like, huh. What if I just got the same job, just like this, at another company? So that I'm doing the marketing directly for a company as opposed to handling all those agency clients.”

He deconstructed his agency job and rebuilt it himself. Now if he has thirty clients, he is earning the salary he’s worth for those 30 clients.

Finally, I spoke with Polly. Her motivation was financial: She wanted to save up money for a house. When she calculated how long it would take her to do that at her current job, she found it was going to be around four years. But they wanted to buy a house next year. So she looked at the available jobs, applied, got the job, and then just didn’t quit.

If this is you, if you're saving up for a big milestone like a house or starting a family – and importantly you have the bandwidth and you have the ambition – that could be your path as well. Just apply to a new job and “forget” to quit the old one.

A quick note on overemployment timelines

Overemployment is not a forever state. You can become overemployed, save up a ton of money, work like bananas for a year, and then use that nest egg to start your own business (like me and Zach) or buy a house (like Polly). Overemployment should be a situation that works for you, not the other way around.

The future of overemployment

I want to talk about the future of overemployment. Overemployment is prevalent, and I think it's only going to grow. We have this perfect storm of conditions to enable overemployment. It’s truly wild how much opportunity there is in this industry, and now is a really good time to take advantage of it.

Factor 1: The workforce has never been more disillusioned.

I'm talking about quiet quitting. I’m talking about this huge trend where employees are finally waking up to the fact that employers are taking advantage of us. They will overwork us and not give us pay raises. They will happily fire us if we cut into their bottom line.

This was a factor that influenced Zach’s decision to go overemployed. “When I started to job stack and realized I could make you know so much more money than I could by just working one job, I was like, ‘Hey, people should know this. People should realize that they're getting screwed over. People should realize that marketing agencies are taking advantage.”

So many people got fired or laid off during a pandemic when especially in the States, healthcare is an absolute must! Yet they didn't hesitate. I think a lot of people are starting to wake up to the fact that if your employer doesn't feel like they owe you anything, maybe you don't owe your employer anything either.

Factor 2: Productivity has never been higher.

Over the years, all this technology has made our productivity skyrocket. Productivity is through the roof. But wages have stagnated. This means you are producing more than ever, you are doing more work than ever, and you are creating more wealth for your company than ever – but you're not being compensated fairly for that wealth creation.

Factor 3: We live in a remote work world.

I really think this is the clincher. You have this unrest. People believe that they're worth more. Then you have the availability. Suddenly you can get your job done in much less time than you used to need.

And finally, the rise of remote work makes it really possible to act on your unrest and extra capacity.

You can sit at home and do more than one job at one time without your employer ever knowing (unless they’re engaged in some dodgy barely-legal employee surveillance shit, in which case, they’ll fire you but it’s their loss).

The conditions for overemployment are right.

But…I don't think they should be.

My spicy take on overemployment

Despite being overall pro overemployment, my spicy take is that I don't think overemployment should exist.

I don't think it should be a necessity. I think that honestly working one full-time job should be enough for everybody to save up to buy a house and send their kids to college. You shouldn't we shouldn't have to manage two, four, eight different workloads or bosses in order to afford the lives that we want the lives and that our parents and our grandparents had.

Overemployment should not become the standard. Side hustles should not become the standard. One job should be enough for everybody.

But that’s not true today. Housing, healthcare, and education costs have flown right up with productivity, but our wages have stayed where they are.

*Per capita out-of-pocket health care expenses have nearly doubled in the last 50 years, even when adjusted for inflation. Source:* *health system tracker*.

That’s what makes overemployment not only appealing but actually necessary in a lot of cases. Today, we are in the kind of situation where being overemployed is almost universally a good thing to be.

For health care.

For a fair salary.

For intellectual fulfillment.

For job security in an under-regulated job market.

Having more than one job is a very appealing prospect. I understand if that's you because it was me too it is me.

Who’s right for overemployment?

There are a few things you need to be a good overemployment candidate.

First, you need absolute buckets of ambition. You need your own drive and to be super self-accountable. Remember, overemployment can be a LOT of money, but it’s not easy money.

It helps if you have an overriding motive, too. Like with blogging, overemployment can be a lot of work. Sometimes the money just isn’t worth it. To be successful at overemployment, you should have a reason to be job stacking beyond “I think it’d be nice to have piles of cash.”
For Zach, he was overemployed just for long enough to start his business. I only did it as long as I had to before I could go full-time on my own business. I expect that when Polly buys her house, she may scale down her overemployment efforts.

Do you want to have a specific amount for your kids to go to college? Do you want a nest egg for retirement? Are you trying to learn a specific new skill? Whatever your reason for overemployment, make sure it’s a good, watertight one.

The right skillset is also beneficial. You want skills that let you do remote jobs where you can build automated systems to do most of the work for you. For example, if you're in programming, digital marketing, writing – any of those can work.

If those fit you, then go for it. If you think you can take that on, there's nothing stopping you from doubling or quadrupling, or octupling your paycheck.

Overemployment is a great way to be paid what you're worth.

Final thoughts

My final position on overemployment: if you can get away with doing it without your boss noticing that you’re slacking, you’re totally fine. I just wish we lived in a world where nobody ever thought, huh, I should take more than one job at a time in order to afford a house/college education/my medical bills. But we do.

Resources:

The overemployed subreddit is awesome for inspiration and Q&A
Wade Marketing does run an Independent Partner Program to help digital marketers specifically start job stacking.
I like the overemployed website.