How to Work Multiple Remote Jobs — and When You Should

Editor's Note: This story originally appeared on FlexJobs.com.

You’ve heard of being underemployed, but have you heard about being overemployed? That’s one of the most recent job terms in the professional world for remote workers working more than one job.

And we’re not talking about side hustlers trying to build a freelance business on the weekends. The overemployed group consists of remote workers secretly working two or three jobs.

If you’ve seen reports of people earning double and triple incomes and you’re curious about following suit, pause first. There are considerations to make before taking on multiple remote jobs.

While working two full-time jobs can result in a much higher income, it will significantly affect your career and personal life.

Take time to consider the pros and cons of adding on a second job. Then, analyze if you can better meet your financial goals by taking on a more manageable side hustle, a part-time job, or starting a freelance business.

Should You Work Multiple Remote Jobs at Once?

So, should you or shouldn’t you? Well, working multiple jobs isn’t a bad idea in general. You might have done it in high school or college, lifeguarding at the city pool during the day and then waiting tables in the evenings.

It’s not uncommon for people to work more than one job after launching a career, either. For example, a teacher who tutors on weekends and during breaks has a second job. Or, an editor who is stretching their SEO knowledge with a freelance business. Both of them are working second jobs.

The key to successfully working multiple remote jobs is ensuring your jobs don’t overlap or interfere with each other. There are varying degrees of theft to consider when analyzing employment laws. You need to ask yourself if you’ll be using property or information that belongs to the employer.

There’s also the concept of time theft. When you’re paid hourly, the employer pays you for your focus and talent. If you’re working two remote jobs that overlap, you’re technically not fulfilling your obligations. You’ll also live with the constant stress of getting discovered. You could impact the entire company’s remote work policy if you are found out.

But that doesn’t mean that you should limit your earning potential to one job. There are times when working multiple remote jobs could be a good choice.

When Working Multiple Jobs Is OK

Working multiple jobs can be substantially easier in the remote work world. Explore some ways you might successfully add a second job to your schedule.

1. When You’re Launching a Freelance Business

Are you considering launching a freelance business or side gig? Though it’s generally acceptable to have a side job, check with your company to ensure that it’s not violating any employment policies.

As a rule, your second job should not conflict with your main job. That means you do it outside of regular work hours, you don’t use company resources for it, and it doesn’t create a conflict of interest.

For example, you generally wouldn’t be approved to work at a call center for one travel agency during the day and a competitor in the evening. But you might be able to work a traditional job during the day and then, for your second job, work from home in the evenings.

2. When You’re in Between Full-Time Jobs

Are you working a part-time job right now while looking for your next full-time role? In that case, you might be able to easily add in a temporary job to help boost your income or fill in some resume gaps.

Ensure you can fully devote yourself to each role when paid by that employer. And don’t forget to factor in the time commitment that a job search will require when considering how many hours you can commit.

3. When Your Employer Knows and Approves

You might be in a results-only work environment (ROWE). Once your commitments are met, your job is considered complete for the week. Or, perhaps you have an extremely flexible schedule.

In either case, your employer might support you in working a second job. The key to finding out is looking closely at your employee handbook before jumping into any conversations or commitments.

You might even find an easy work-from-home job in a field you’re passionate about.

For example, you might pursue a customer service job for a company related to dogs and cats if you’re passionate about animals. In that case, it’s easy to see how a second job might fit well into your current commitments and get approved by your current employer.

How to Work Two Remote Jobs

When you’ve analyzed all of the scenarios and are ready to add on another job, take the time to strategize some key areas before launching your search.

1. Avoid Overcommitting on Workload

Acknowledge that being a high performer in multiple roles simultaneously will be challenging — and perhaps impossible.

If you’re used to saying “yes” to extra projects, now is the time to say, “Let me check my task list first.”

Be realistic about what you can handle while still submitting excellent work. To maintain your work quality, you might need to change the time frame of when you can get things done or how much you take on.

2. Make Sure Your Employer Is on Board

Do you love your current job? Or, even if you don’t love it, do you need the paycheck? If so, it’s worth taking the time to talk it over with your employer.

The HR department often has a quick vetting process to ensure that your second job isn’t a conflict of interest.

If you’re looking to follow your passion, like teaching art to kids or growing a skill that will help boost your career value, there’s a good chance your leader will be supportive as long as your work performance doesn’t suffer.

3. Manage Your Time Effectively

Mastering time management is key to succeeding with multiple remote jobs — especially when you have flexible hours. Without an employer putting boundaries on your work time, you need to take charge of your daily commitments.

Get in the habit of checking your schedule every morning to ensure you don’t miss a meeting or a deadline for either job.

Make careful to-do lists and create a routine for keeping them updated with tasks you need to prioritize from each role.

4. Negotiate Multiple Schedules With Employers

When analyzing where and how you’ll fit a second job, consider scheduling alternatives you can present to your employer.

That might mean a flexible schedule that allows you to work earlier or later in the day. Maybe you can work a compressed workweek at one of your jobs so your hours are complete in just a few days.

Look at your job duties and consider where you must overlap with other team members and current schedule policies. Then, bring an organized presentation to your employer to see if there’s room to negotiate.

5. Set Schedules and Boundaries

Above all, you must be protective of your schedule when working multiple remote jobs.

Unfortunately, your personal life will likely take a hit, but keep your eye on the prize, whether that’s paying off some extra bills, saving for a vacation, or simply putting away more for retirement.

You’ll need to set some boundaries with others once you’ve committed to both jobs. Let family and friends know that you’ll be busier than normal for a while, and get in the habit of checking your calendar.

Before you set aside work, ensure you can realistically make up those hours or complete the tasks. If not, you’ll need to hold your boundary so your work performance doesn’t suffer.

Disadvantages of Working Multiple Remote Jobs

It’s not uncommon for people to work more than one job. However, there are some significant disadvantages to working multiple remote jobs. Here’s what you need to know.

1. Work-Life Balance Is Tough

Many people struggle with achieving work-life balance while holding one job.

While remote and flexible work makes work-life balance easier to achieve, adding a second job makes it harder, regardless of how many extra hours that second job adds on.

You may work well over 40 hours a week, depending on your jobs. And even if you keep that number under 50 or 60 with one full-time and one part-time job, that’s still a lot of work hours.

You can’t spend those hours with family and friends or care for yourself. Working that much often leads to burnout and can impact your physical and mental health.

2. Job Performance Suffers

When you work multiple remote jobs, doing an outstanding job in either role is harder.

Even if you carefully manage your schedule so you have time to focus on one job at a time, you never know when your boss, co-worker, or client may ask for some extra hours.

When your hours are stretched, you might discover that your creativity and decision-making skills are fatigued long before you get your hours in. It’s hard to stand out and get a promotion when your work efforts are always just enough to get by.

And remember, your next job opportunity might depend on the reference your current leader provides.

3. Taxes Might Take You by Surprise

Taxes are a thorny issue when you work multiple remote jobs. Working two remote jobs might bump you into the next income bracket for state and federal taxes.

Neither employer is withholding at the higher rate, and before you know it, you owe more at tax time than you anticipated.

It’s worth taking the time to analyze your potential gross income and the total you’ll pay in taxes. When you see the extra income you’ll bring in, analyze if it’s enough to make the extra hours worth it.

Is It Illegal to Have Two Full-Time Jobs?

Understanding the legalities of working a second job is a bit complex.

Individual states have different boundaries for how much an employer can restrict an employee’s ability to earn money, regardless of noncompete agreements. However, some nuances involve where you live, where the company’s headquarters are, and more.

In most cases, having a second job isn’t illegal. But if you’re wondering how to work two full-time jobs simultaneously — as in during the same hours without either employer’s knowledge — you run into the concept of time theft. Not to mention, employers have the right to protect their proprietary information. Working for a competitor can be grounds for dismissal or worse.

Most employment, at least in the United States, is “at will,” meaning your employer can terminate your employment at any time. To legally work two jobs, you’ll need, at minimum, to keep your work hours separate, limit your use of employee-provided resources to each employer, and explore any business overlap between the two companies.

Start your research with your employee handbook, then expand to state laws. Seek answers from certified legal professionals vs relying on the experiences of other remote workers who may not have identical situations or contracts.

Choose Your Remote Work Journey

Working multiple remote jobs is a juggling act that isn’t for the faint of heart!

But there are many reasons why it might be a great choice for you, such as gaining skills for your resume, getting a temporary boost in income, or getting your foot in the door at your dream company.

Carefully analyze your current time commitments, where you can fit another job in, and how you’ll include time for self-care with a busier schedule. Consider if the solution might be a new full-time position with better pay.