Trust is the glue that keeps relationships together -- personal and professional. But when work happens behind screens and you can't see your team, trust can easily get eroded. One "I'm sorry I have to jump, my cat's eating my son's homework" too many and it's easy to understand why you might be feeling a bit skeptical about what your team is actually doing during their work hours.

Are they lounging on their couches, munching on potato chips and drinking ungodly amounts of soda? Binge-watching The Young and the Restless?

Or -- maybe worse (?) -- working for another company too?

Eek. Remote work models have come with plenty of challenges -- the last thing you needed to worry about is your people dragging the day away while working full-time for someone else too.

Is it wrong, though? Should you expect your employees to be exclusive to you, or is it acceptable for them to take on side gigs/ second jobs?

Let's approach this question from different perspectives...

Performance Over Time Logs?

Essentially, full-time employees are paid to perform their job for a given amount of time (usually 8, frequently 9, sometimes more.) So, if someone is working remotely and juggling two jobs during the same time span, it means that, theoretically, they are not working their full-time quote for either of the jobs.

In theory, it should mean that they are not performing optimally with either, and in some cases, can even be detrimental to the overall success of both companies.

On the other hand, if an employee is doing both jobs efficiently -- meeting all deadlines for both positions, it could (generally) mean two things:

1. They are experienced at what they do, and they can do things in less time than the average employee working the same job.
2. Their task list isn't... long or hard enough.

In this case, what you have to ask yourself, as the manager is: "Do I need them to do more?"

If the answer is yes, then you may need to look into the employee's performance over time So, if an employee is taking too long on a task or not investing enough energy in certain projects, you'll be able to spot a trend.

If the answer is no, then you may need to have an open conversation with the employee about their workload and how they are managing it. It's important that everyone in your team is on the same page regarding expectations and boundaries.

Ultimately, what you need to know to lead your team is what you value most: is it time logs, or is it actual performance? If time logs are your main concern, then, yes, a remote employee working two jobs isn't exactly ideal. But if actual performance is your priority, then you may be open to the idea of allowing them to take on a second gig without sacrificing quality of work.

It's all about understanding what makes your team successful and how you can help each individual accomplish their goals while still contributing to the collective goal of the company.

What About Mental Health and Morale?

It's also worth considering how taking on two jobs at once can affect one's mental health, morale, and thus, productivity. Being able to have a work-life balance is important to stay focused and motivated. And while many might be able to juggle two jobs at once for a while, most will eventually burn out.

There's only so much battery life to a human brain -- and no matter how great your employee's intentions are, if they keep on burning the candle at both ends, there is a chance that their performance will suffer.

That's why it's important to understand how taking on a second job can affect your team member's morale and mental health, especially if they are working full-time already. Talk to them openly about the impact of taking on a second job and make sure that there is mutual understanding between both parties.

Who's Doing This?

There's also the question of who in your company might be taking on two jobs at the same time.

Gavin Schubert has been consulting on HR, Governance, and Management for over two decades, and he made a very good point (particularly if you value performance over logged hours.)

"Outside of senior management (and sensitive middle management roles), no. It's no different to having two physical jobs.

Unless your role is quite senior, there's rarely any justification for an employer to expect exclusivity."

-- Gavin Schubert, Management Consulting Director

So, in theory, if someone outside senior management (who is likely also paid very well) is taking on a second job, it might be okay -- as long as they are not compromising the quality of their work and can still meet their deadlines.

It's all relative, of course. In a startup, every person wears multiple hats. So, if one of the employees decides to double down and take on a second job, it might affect the overall performance of the company as a whole (especially if that employee is involved in multiple projects and other people in the team depend on them.)

The Legal Question

From a legal standpoint, working two full remote jobs simultaneously might be tricky. It's important to have a clear understanding of the terms and conditions between you and your employee, both regarding hours worked and rate of pay.

It's also important for both parties to understand that they are responsible if any legal issues arise from the arrangement. So, having everything in writing is essential, from job description to expectations to how vacation time or sick days are handled.

Of course, you'd also need to consider security matters, particularly if the employee is working with sensitive data. So, make sure to properly vet side gigs/second jobs and ensure that employees have the necessary security protocols in place while accessing any confidential information.

Last, but not least, both you and the employee need to consider any kind of potential conflicts of interests. If the second job is in a related field or even with a competitor, it might be worth having an out clause that allows you to terminate the arrangement if needed. However, make sure your employee is fully aware of the arrangement and that they give consent.

"If you are not senior, but handle market-sensitive information, it may be reasonable for your employer to ask that you do not work for competitors. However, any such restraint ought to be backed by sufficient working hours and pay. It is never a justifiable request for minimum-wage jobs, in my opinion.

If you are meeting the reasonable expectations of both jobs, you've earned the rewards."

-- Gavin Schubert, Management Consulting Director

Gray Areas, Gray Areas Everywhere

"Working multiple remote jobs is ok as long as you consult your first employer’s handbook to see if they have rules against it (and then follow those), and are upfront and honest when/if someone asks. Obviously as a freelancer, working for multiple clients is totally fine. But with full-time employment, it’s a grey area that needs nuance."

-- John Doherty, Founder, EditorNinja

Honesty goes a long way -- and so does reading the fine print (or, in the case of employers, making sure the fine print is there in the first place and that it is reasonable for both parties. In many ways, working two remote jobs is no different than working two physical jobs -- something people have been doing for a while.

Yet, with remote jobs, comes the added challenge of ensuring that your employee is not compromising quality and that their workload is sustainable. It's all about having an open dialogue and establishing boundaries on both ends -- but it can be done as long as you are thoughtful and considerate.

To Trust or Not to Trust -- That Is the Question!

So... how many people actually hold two jobs while working remotely?

It depends on who you ask. Some stats say about 10% of the US workforce has a main job and a side gig. According to some other sources, the number of people juggling two jobs (e.g., one full-time and one part-time gig) has grown since March 2020.

Yet, little research is available on whether remote employees work multiple jobs at once.

The rumor mill has it the number is high. But reports of such behaviors are still actually scarce and the lack of data makes it difficult to know whether this is a widespread trend or not.

In fact, in some ways, what we don't know about remote employees juggling two jobs at once is just as important as what we do know. In a world where trust and transparency should be key, being able to gauge how many employees might be taking on extra work is a matter of respecting their right to privacy and allowing them to be open about any potential side gigs.

Above all, this conversation needs to start with the employer -- understanding what is considered reasonable in terms of workloads and making sure your team members know that you are there for them if they need it. After all, trust is a two-way street, and when it's present, great things can happen.

In this paradigm, whether or not your employees hold two (or more) jobs while remote is of little to no consequence. What matters more than anything is that both of you are transparent with each other and that whatever work needs to be done... gets done.

Here's another perspective too: the freelance platform market size was estimated at $4.39 billion in 2022, and it is expected to grow at a compound annual growth rate of 16.5%. This is a clear indication that freelancing will not only continue to exist -- but it will keep on thriving too. Furthermore, 60% of freelancers make more than they did in their full-time positions. Soon enough, you might have to worry about your full-time employees going freelance, rather than taking two or three remote jobs -- so if you want to keep them around, make sure you offer a competitive and attractive package.

At the end of the day, it all comes down to trust and transparency -- regardless of how many remote jobs or side gigs your employees choose to take on. As long as everyone involved is aware of their responsibilities and feels secure in the arrangement, multiple job-holding can be a beneficial thing for both parties: the employees enjoy the growth and the financial incentives, and the employers reap all the benefits of working with experienced people who can cross-pollinate knowledge and bring fresh perspectives to the team.

Of course, it's ultimately up to you to decide whether you can trust your employees to manage multiple jobs while still delivering quality work -- but with open communication and a clear set of expectations in place, it could be a win-win situation for everyone involved.