What You’ll Learn: Discover the ins and outs of working two remote jobs. Find out about the pros, cons and ethics, and if it could be right for you.
Working two remote jobs—also called overemployment—has both advantages and disadvantages. It can boost income and job security, but comes with legal, ethical and practical risks. While it’s legal in many countries, some employment contracts may include clauses that restrict it. Violating these can lead to termination or legal issues.
Among the most obvious benefits of remote work are the convenience of your own schedule and hours of saved commute time. However, a lot of remote workers are using these benefits in a rather interesting way: working a second job.
At a glance, working two jobs doesn’t seem like a bad idea. You can make more money, diversify your expertise and get more financial security than a single job can offer. Who doesn’t love that?
However, the realities are often complex on closer look. Becoming a multiple jobholder is not only difficult due to the sheer workload. It also carries some risks.
That leaves us with a few questions. Is working two remote jobs legal? Is it sustainable? And if people are already doing it, how do they make it work? This article has your answers.
Can You Work Two Remote Jobs at the Same Time?
We’d love to give you a short yes/no answer. But as it turns out, whether you can work two remote jobs at the same time depends on more than one factor. Largely, there are three important questions that decide if you can work multiple jobs:
- Is it legal to work two remote jobs?
- Does your employer allow it?
- Is it ethical?
We’ll take these questions one by one.
Is It Legal to Work Two Remote Jobs?
Let’s address the legal considerations first. The United States has no law that prohibits you from working two or more jobs simultaneously. The same is true in Canada, the U.K., Germany and many other countries. In other words, working multiple jobs isn’t inherently illegal in most places.
However, does that mean working two jobs is always legal? The answer is no, and the reason is usually your employment contract, as we will see now.
Does Your Employer Allow You to Work Two Jobs?
Although employment contracts vary across companies, many have an exclusivity clause that doesn’t allow you to be employed elsewhere while you’re working for the company. Some employers don’t outright ban working second jobs, but require employees to seek approval before doing so.
Moreover, many employment contracts also have a non-compete clause that prohibits employees from working for a competitor during or after their employment with the company. That means if you are working for such a company, not only can you not work with their competitor now, but also not for a specific period after you resign.
That’s not all. There are other cases where working for a second employer can conflict with the interests of the first (and vice versa). For example:
- If you are working for an employer that’s a supplier or client of your other employer, or is directly related to them in any other way
- If you are using the resources provided by one company (such as a laptop, software, internet connection, etc.) for your job at another
- If you are working for one company during your working hours for another company (this can be considered a form of time theft)
Each of these situations can be considered a conflict of interest.
So, what happens if you breach the contract in any of these ways?
For starters, your employer(s) can terminate you right away. However, in some cases, you can also be directly sued for time theft.
This is why it’s best to avoid jobs that can lead to such issues. As a general rule, check with your employment contract and employee’s handbook to find out about your company’s stance on its employees working second jobs.
Is It Ethical to Work Two Remote Jobs?
We are entering a grey area now, since what may seem perfectly ethical to someone may seem downright unethical to someone else. When it comes to working two jobs, the line often gets very blurry, even more so in remote jobs.
But here’s the general perception. As long as your remote jobs are different roles in different industries and do not cause any conflicts of interest, it’s generally considered OK to work two jobs. After all, what you do with your time should be your decision.
However, if you have signed an employment contract that bars you from working another job, working two jobs goes against that contract and is unethical. This is especially true if it can lead to any form of conflict of interest. It can also lead to ethics concerns if:
- You are not meeting your job requirements for either position
- You are violating any company policies
- You are not transparent with your employers
So, back to the question—is it ethical to work multiple remote jobs? We leave it to you to decide for yourself. At your own risk, of course.
The Rise of Overemployment and Remote Job Stacking
Despite the risks and debate around working two jobs, some remote workers are not deterred. According to a recent Resume Builder survey of 1,250 full-time remote American working adults, roughly seven out of every 10 remote workers have a second job outside their first job.
In fact, when you look at the big picture, the U.S. Bureau of Labor Statistics says that about 5.2% of all employed Americans have multiple jobs as of August 2025. That may look like a small percentage, but that’s actually 8.48 million multiple jobholders.
It doesn’t stop there. Terms like “double-dipping” and “overemployed” have been on a steep rise over the last few years. In fact, there is a website called overemployed.com that calls itself a community that helps people earn “double income and achieve financial freedom.” There is also a subreddit with the same name with weekly visitors of 335,000 and a Discord server with over 58,000 members.
These factors suggest that people are interested in, or at the very least, curious about working two jobs. The overemployment movement is on the rise, with more people than ever stacking multiple jobs. There are several reasons this is happening. Let’s take a look at the “whys” behind it.
Reasons for Working Two Jobs
Holding multiple jobs is not a new thing—quite the contrary. Moonlighting, which is the practice of working a secondary job outside the working hours of the primary job (usually at night), has been around for decades.
However, in many cases employees have more freedom. They may be able to work hours of their choosing or make their schedules how it works best for them. Though many remote jobs now track their employees with various methods, some also still give employees more autonomy.
This convenience is a big facilitator for every remote worker who is or wants to be overemployed. But what really drives them to hop on a second job?
According to Resume Builder’s survey, there are multiple reasons, such as:
- Having more money
- Paying off debts
- Investing and saving for the future
- Getting more diverse experience
- Following a career passion
- Avoiding boredom
Then, there is another big reason: job security. Layoffs have reached a new high recently; in 2025, the number of layoffs is the largest number of layoffs since 2020. With job security becoming so elusive, having multiple jobs is how many workers are trying to attain greater job security..
The reasons for having multiple remote jobs aren’t negative. If you are transparent, adhere to company policies and avoid any conflict of interest, it is possible. However, there are some additional hurdles to consider. For example, burnout, stress and time management concerns are real. Let’s explore some tips that could help.
Setting Work Boundaries to Manage Two Remote Jobs at the Same Time
There are mainly two ways you can go about working a second job besides a full-time primary remote job:
- Work a part-time job
- Work a full-time job
Doing part-time work is easier when you already have a full-time remote job. But either way, you will need more structure and systems to make this juggling act sustainably manageable.
Although working two positions is challenging, a few remote work productivity tips can help you navigate this work situation.
1. Establish Priorities
It’s important to get all the core things done for both jobs—and on time. To do that consistently across two jobs, you must prioritize the right way.
Define your non-negotiables across the two jobs. These can be looming deadlines, meetings or any deliverables. Actively communicate in advance whenever you are pushing a task for later.
2. Block Your Time
Time blocking is an effective time-management technique where you block a period of your time to do nothing but one specific task. If you’re stacking jobs, time blocking can help you divide your time between two jobs.
For example, you can block two hours of mornings for doing Job #1 and focus on just that. In the afternoon, you can then turn to Job #2 and fix another three-hour slot for it. This approach throughout the day will help you keep your attention and work focused on one job at a time, helping you finish work faster.
3. Keep Your Calendar Organized
If you are working two remote jobs, good calendar management skills are non-negotiable. You might need to manage deadlines, schedule meetings with managers or get on calls with teammates. You’ll have a variety of tasks that need done in any given week. Managing these things across two jobs can be tricky, which is why it helps to put everything organized well on your calendar.
Add all your important tasks and events to your private calendar. Use different colors for the two jobs to avoid confusion. You can then use this calendar to create your professional shareable calendars for the respective jobs. This will help you steer clear of potential deadline conflicts and overlapping meetings.
4. Set Communication Boundaries
Thanks to the nature of remote work, you generally don’t have to be physically available all time for both jobs. Nevertheless, you must be available and visible as necessary. To make this feasible when working two remote jobs, a good idea is to set clear expectations and boundaries on communication. This can mean:
- Defining your availability for each job
- Setting clear expectations about your response time for emails
- Blocking your calendar out when you are not available for one employer
5. Separate Your Devices and Accounts
Imagine sending a deliverable to one employer, only to realize later that it was meant for the other. Mess-ups like these can be more common when you are using the same set of devices for both jobs.
This is why many job stackers prefer separating their hardware, with one device having only the data and documents of one employer. In fact, you can also consider setting up two different work desks. This way, shifting to the other desk will give your mind a psychological cue to switch context and not mix things up.
Quick Tip: While these tips are generally helpful, your choice of the two jobs is much more important. Choose a second job that balances the demands and workloads of the other. Choosing two highly demanding jobs is likely to lead to eventual burnout.
Side Hustle vs. Second Job: What’s the Difference When Working Multiple Remote Jobs?
There is also another option besides working two remote jobs: a side hustle. It is similar to a second part-time job as an additional source of income on top of your primary job. However, a side hustle may give you more control over your hours and earning potential.
Side hustles can usually take the form of freelancing, consulting and other myriad personal endeavors like a business. It’s totally up to you what you want to pursue—and how. The real question is, should you really pursue a side hustle instead of a second job?
Let’s look at what the differences might look like for you:
| Side Hustle | Second Job |
| More autonomy over your working hours | Fixed number of working hours |
| More control over how much you make | Fixed salary or, at best, fixed hourly rates |
| Can be highly unstable; you may not make anything initially | Usually very stable; you start earning as soon as you join |
| Freedom to choose the work you do | Negligible freedom once you join |
| Can be difficult to manage | You only need to manage your work |
| More diversity and learning potential | Repetitive tasks |
To sum up, a side hustle can come with more adventure and more earning potential, but also may add more uncertainty and responsibilities. A second job, though, can offer stability and a fixed flow of income, but may have a set hourly rate and be limited to the specific type of work you were hired to do.
So which one is best for you? The answer depends on what matters to you the most.
If you love stability, a second full-time or part-time job could work for you. However, if you want to try something new or build something of your own in the long run, trying a side hustle might be the path for you.
Can Working Two Remote Jobs Actually Work Long Term?
We’ve talked in detail about working two jobs. Now let’s zoom out a little and look at the overall picture.
Doing multiple jobs at one time can be a means to earn more money, learn new skills, gain job security and more. For many, second jobs are also their way to follow their creative interests outside of a higher-paying job.
The reasons are wide-ranging, and each might be enough to make you go for it. But on the flip side, working two jobs is not something most people can pull off easily.
You are going to need discipline, strong time management skills and resilience. The stress and pressure of juggling two sets of responsibilities can often get overwhelming. In addition, your personal life beyond work could suffer.
With these hiccups, how long can you sustain multiple jobs?
There isn’t a clear answer. It depends on whether the pros outweigh the cons for you, as well as on your goals, priorities and management skills.
Is Working Another Remote Job Right for You?
Ultimately, working multiple remote jobs is like many other rewarding activities. It comes with its unique set of challenges and risks. You need careful planning, legal awareness, motivation and strong personal discipline to make it work.
Working two remote jobs is possible, and it can be rewarding. Yet the risks and downfalls also play a large role.
Weighing the pros and cons for yourself is critical. If you’ve covered the bases in terms of legalities and ethics, you’ll need a solid plan in place to fill both job roles successfully. You’ll also need to ensure you have time for your own health, self-care and relationships outside of work to maintain balance and your personal well-being.
If you want to get better at managing remote work—with or without two jobs—we at SUCCESS have prepared a detailed guide for you. Download your FREE copy of our Remote Work Guide here!
Photo by Miljan Zivkovic/Shutterstock
