How to Manage Two Remote Jobs?

How to manage two remote jobs

Is Working Two Remote Jobs Illegal?

In most cases, working two remote jobs isn’t illegal as long as you are not breaching any employment agreement. These days, with more and more companies allowing remote work, many remote professionals are working two jobs. If you are considering a second job, check your employee handbook and other documents to see if your company allows it.

I have been freelancing and juggling several remote jobs for three years now. Committing to more than one employer means I have to wear many hats at different times during the day. And if I had to summarize my success in four words, it would be “communication, organization, and time management.” I am not confident I could have made it this far without these three skills.

In this article, we’ll discuss what it means to have two remote jobs, the perks and drawbacks, and how to minimize the impact on your life.

Managing two remote jobs

Overemployed Trend: Insights

The over-employment movement, also known as moonlighting, is a growing segment of non-contingent, high-income professionals working two full-time jobs —and it has thrived post-pandemic for various reasons. Among them is the increasing popularity of remote and hybrid work.

A survey in 2023 of over 1,000 employees working fully remotely by Resume Builders reveals that 8 in 10 respondents have worked more than one full-time job in the past year. The same study showed that 52% of these over-employed workers make over $100K.

This trend will continue as more people join the remote workforce and pursue financial freedom. Plus, the safety net that comes with having another job that pays as much as your current one is a bonus. For instance, during massive layoffs, you can have a cushion with your second job.

Should I Work Two Remote Jobs?

It depends. There are several factors to consider before deciding to work two remote jobs. For instance, juggling two remote jobs mean:  

  • It can be tricky to have a work-life balance: With one job, it is already challenging to maintain a work-life balance. Although remote work offers flexibility to achieve that, adding another job can make it even more difficult. 
  • Lack of focus: Splitting your attention between two jobs can lead to a lack of focus and concentration, which may result in lower productivity and lower quality of work.
  • Tax implications: Working two jobs can complicate your taxes, as you may have to file two separate tax returns or pay additional self-employment taxes.
  • Legal issues: Depending on the terms of your employment contracts, working two jobs may be prohibited or violate non-compete agreements.
  • Burnout: Working two jobs simultaneously can lead to overwork and burnout, especially if you have a tight deadline for both jobs.

However, working two jobs is acceptable when:

  • You are freelancing or doing a side gig: Many people work a full-time job while also freelancing or doing a side gig to earn extra income. It is generally acceptable as long as the side job does not conflict with your primary employment not violate any non-compete or confidentiality agreements.
  • Your employer knows and approves: If your employer is aware that you are working another job and approves of it, then working two jobs is acceptable. This could be the case if your employer has a part-time or flexible schedule policy or you are taking on a side job.

It is critical to note that even in these situations, you still need to manage your time effectively. You must also ensure that your performance at both jobs meets or exceeds expectations.

8 Tips to Handle Working Two Remote Jobs

Having two remote jobs is exciting. You double your income; you can avoid monotony due to the variety of projects you’ve to work on and not to mention the opportunities to network.

But as I’ve learned over the years, that euphoria can quickly disappear if you don’t have a solid plan to manage both jobs. Here are some tips to help you prevent issues working two jobs remotely:

1. Get Prepared For Working Two Remote Jobs

Unlike freelancers working with different clients, working two jobs means dealing with different work schedules. So, first, make sure to apply for realistic positions with flexible working hours or a monthly schedule you can combine. If you have to log in at 8 am for both jobs until 5 pm, you can’t really build a healthy schedule – unless you don’t create a clone. 

After that, it’s time to plan how to include a second remote job:

  • Weekly total hours. How many hours do you want to dedicate to the second remote job? Depending on the nature of the first employment, you can range between 5 and 15 hours. However, if your first role requires over 40 hours for a stressful position, perhaps getting a side job isn’t the best choice.
  • Set your availability. Have an overview of your current commitments and identify when you can be available for your second job. If the other role doesn’t require synchronized work, you can pick the time that suits you better. When you find a job that requires weekly meetings, save the day to set your availability. 
  • Take care of yourself. Plan the week. Don’t take out time off from your hobbies or leisure activities. With your busy life, you will need your time off to avoid burning out.
  • Draft a schedule. Before starting the interview process, schedule it into your calendar. When you talk with your future employer, you can give a realistic overview of your availability.

2. Prepare The Tools You Need

The first thing, you must get your tech ready for the job. Research which tools you will need to use working two remote jobs and try the company’s platforms.

With a tight schedule, you can’t waste time with weak Wi-Fi or low-quality devices. Cheap tools will negatively impact your performance and, in the long run, your motivation.

For example, I had a pretty slow old laptop when I started working remotely. At some point during the day, I had to take breaks to allow it to cool down before continuing my work. Fortunately, at that time, I was contracted to only one employer, so I was able to manage the situation. But I don’t see how I would have survived that with the same defective computer now that I’m working with a couple more clients.

So, if you relate to this situation, here are a few laptops to consider if you are getting a second job: 

  • MacBook Pro – It’s one of the most expensive models, but it incorporates everything you need. 
  • Dell XPS 13 Inch or HP Spectre x360 – These are two options if you prefer Windows over iOS. 
  • Acer Aspire 5 – Acer is one of the most affordable options if you are new to remote work and need to understand which system works best for you. 

3. Make A Routine

Setting up a routine is the mantra for all of us working remotely. It doesn’t matter how many jobs you are on. You need a schedule and a routine. Plan the work a week ahead and stick with the plan. 

If extra tasks come in, you know if you can keep up with them and speak about them with your team. You can use apps, and to-do lists to organize the work and have reminders. Just follow the working schedule you give yourself. 

4. Keep a Consistent Work Schedule

In other words, don’t overwork. While this article is all about advice to optimize your time working two remote jobs, keep in mind that one thing is optimizing time management, and another thing is planning tasks when you should do something else. Don’t plan to overwork or complete more tasks at the same time.

None can do two things at the same time. 

For example, as a writer, it’s tough to jump from one topic to another, hoping to finish two articles (or more) at the same time. From my experience, you will end up being late on both jobs, delivering low-quality outcomes. And catching up with two jobs is more demanding than one! 

5. Keep Up a Healthy Lifestyle 

While working two jobs, other areas of your life might suffer. Your laundry piles up, dust everywhere, and you need to go out shopping. We have all been there. 

If you dedicate more time to work, saving time for other things is essential. When you shop and cook, try to think for all week. You can make salads, cold pasta, and veggies that can stay in the fridge for a few days. You will have a healthy and ready meal that requires just easy additions like eggs or cheese. Likewise, instead of spending your day off cleaning, you can clean a small area of your house every day after lunch.

6. Remember You Have Friends And Family

This tip doesn’t need much explanation. When you struggle with two remote jobs, loved ones are the first ones to suffer. It sounds like a smart choice in the beginning. 

Deadlines will end, and you will eventually catch up with tasks. That’s never true. Jobs add up, you have other commitments, and your friends have a life too.

Don’t neglect your friends. Time off and socialization energize the spirit and motivate you when returning to work.

7. Prioritize Self Care

In the same vein, you need to take care of yourself. Now that life is slowly starting again, book a concert or an outdoor activity. Don’t skip your exercise or painting course. 

When you plan your week to include a second job, you can’t take time away from your free time. You can wake up earlier or sleep later to work. But save time off in your calendar for yourself.

PS. This is the most crucial piece of advice to remember wherever you are doing one, two, or three jobs at the same time.  

8. Remember Your Goals When Working Two Remote Jobs

After a while, working two remote jobs gets tiring, even with the best routine. Sometimes motivation goes down, and you start wondering why you are doing this to yourself.

When this moment happens, take a deep breath and remember your goals. You wanted more financial security, to improve your skills, or save extra money for the next holiday. Bad times are always there, but the benefits of two remote jobs are worth the effort.

Benefits of Working Two Remote Jobs

Working two remote jobs has several benefits, including:

Benefits of working two remote jobs
  • Expanding your network. You will interact with different professionals from different companies, which can open doors to new job opportunities or career advancement.
  • Potential for increased income. Having two jobs means that you will be earning from both, and this can help you reach your financial goals faster.
  • Help you acquire new skills. Different companies will have different requirements and demands, challenging you to learn new things and improve your skills. As a result, you will have a broader skill set, making you more valuable to employers.

Augment Your Income By Working Two Jobs the Right Way

That was it. Working two jobs is challenging, but it’s also worth it. Once you move on from the initial tiredness, you will see how much your skills are improving. New opportunities will open for you, and you will be able to do things you wouldn’t ever dream of – I promise!

The most important thing about working two remote jobs is motivation. Always remember where you want to be in the next few years, and write down a schedule to follow. And, always look at your bank account at the end of the month. You will see your effort materialized in numbers that you can spend on all the fun activities you want.

Good Luck!


1. Do I need to speak with my manager about having a second job?

Not necessarily. However, honesty is often the best option. You can speak with your manager and be honest about why you are looking for a second job and what type of role you want. Remote jobs usually allow more flexibility. If you have a part-time position, most likely, your manager will understand and help you plan your tasks accordingly. Remember the size of your company and the flexibility it can provide you. Being honest with your manager and team will help set up a realistic workload without impacting the rest of the team.

2. Can you have two full-time jobs legally?

You can, but always check the business and legal implications of having two remote jobs. There are some tax restrictions or limitations when it comes to getting a second job. For example, working for a competitor is never allowed. Also, you can’t disclose information about current projects or the company’s Intellectual Property. Or solicit current customers or vendors from the employer.
If you don’t respect the terms of employment on the contract, you might be subject to liability. 

3. What are the best over-employed jobs to have

Here are some examples of jobs that could be suitable for overemployment: Virtual Assistant
Software Engineer, Freelance Writer, Data Analyst, Consultant, Translator, Graphics Designer
Product Manager.

4. Is 2 remote jobs a bad idea?

Working two remote jobs can be challenging, and it’s not for everyone. It requires excellent time management, organizational skills, and the ability to balance workload effectively. 
However, whether or not it’s a bad idea depends on how you can manage various factors, including burnout, your ability to focus, conflict of interest, and limited time for your personal life.


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