Moonlighting – job cheating or smart strategy?

Find out what moonlighting means, why it is a hot topic, and how to transform it into a win-win situation.

Woman researching moonlighting

Moonlighting is a show. And a movie. But more importantly, it is another way we work. According to the Cambridge Dictionary and in the simplest of terms, moonlighting is the act of getting an extra job, often without your main employer’s knowledge, which sounds like nothing new. We, our parents and their parents are used to side gigs meant to fructify a hobby or bring extra income. However, moonlighting might just be a tad more than that—and feel different, too, for both employer and employee.

Getting a second job may be a smart strategy if you can manage it. But to your employer, it might look like cheating. Why is that? And why might it still be worth considering? More importantly, how can you ensure your side gig is ethical and worthwhile, especially in the current professional landscape? Let’s explore these questions and more.

Making it official

We all know a grandma who, when she was young, used to spend hours knitting or sewing after her day job to earn some extra money on the side. Professionals of any kind, think plumbers or electricians, would similarly use their skills outside their day-to-day job to supplement their income. While for some, their side business was an actual, registered company, most just started by helping a friend and building from there, never really referring to it as a second job, or treating it as such, for that matter.

Today—in a highly digitalized world and a much different economic landscape—finding a proper, contract-binding second job is commonplace, or at least more so than you would think. According to The Bureau of Labor Statistics, 5.3% of workers had multiple jobs as recently as December 2024. But what about paths like freelancing and other self-employed side hustles? A 2023 SkillSuccess survey found that, at the time, 6 out of 10 people were engaged in moonlighting jobs, meaning 56% of workers. Just by comparing these statistics we can safely assume that most of the time, employees do not make it official to their primary employer that they have a second job. Why is that?

For obvious reasons, you would think. But no. While some companies may have policies that forbid this practice, moonlighting is not illegal or unethical as far as most US states are concerned. Thus, losing your primary job is not the main concern here. Rather, employees are afraid of potential setbacks they could encounter if found out, such as being disregarded when it comes to opportunities and potential promotions. On the employer’s side, this makes sense for a few reasons—let’s dive into them.

The performance dilemma

Imagine the following scenario: you are an IT professional working a regular 9-to-5 job. You are comfortable with all your tasks, perform adequately as a routine, and are an all-around good employee. To earn some extra money for your next holiday trip, you find a freelance opportunity online—well-paid, a weekend’s worth of time. It goes so well you decide to make a habit of it, getting side gig after side gig until one day, you miss the deadline for a project at your primary job.

This is the kind of scenario employers fear. By dividing your attention, you risk underperforming, not meeting expectations, or simply deciding you will bet everything on the side gig life you are building rather than keeping your primary employment. While many cannot handle the uncertainty of freelance work, others enjoy the autonomy it gives them, ultimately deciding to drop the 9-to-5 lifestyle for good. And even if they don’t, they’re exposing themselves to tangible risks such as fatigue and burnout, both of which compromise the quality of their work on all fronts. What this all means is, to your employer, a moonlighting work could qualify as time theft or even a violation of ethics.

Another heavy concern for the employer is the potential conflict of interest. For workers who opt for side gigs in the same field, like a programmer doing programming on the side, too, employers might feel like the worker is infringing on intellectual property, or that they might breach the company’s confidentiality—by mistake or otherwise. 

The good news is, most workers are just trying to earn extra income without putting their main gig in jeopardy. Others are looking to further their skills in ways their primary work doesn’t allow or help them to. A few are even trying to monetize hobbies they like, just so they have an incentive to do those pleasant hobbies. That said, how do you navigate this fine line between the two jobs? How do you turn moonlighting into a smart strategy? How do you do right by your employer?

What you can afford

Before jumping the moonlighting train, you should ask yourself this question: can you really afford to do it? If you’re looking at your schedule, then at the clock and the calendar, you might identify some free hours during the evenings or weekends. However, how many of those free hours could be working hours?

While an extra income might be worth the effort, it’s not worth your physical and mental health. It’s not worth underperforming at your main job, either. To help you get a better perspective, put it on paper or create a simple document: see how you’re spending your potential extra working hours and whether those activities could be sacrificed or otherwise accommodated. Remember, a moonlighting gig brings more than just extra money—it also adds pressure and stress. You must first make sure you can handle it without burning yourself out.

Smart decisions for smart outcomes

Sometimes, you just need to make a buck on the side. Other times, and more typical of today’s professional landscape, you want to try something new, develop some skills, or explore a new industry. All of this is understandable, commendable even. However, you must be cautious in the way you choose your moonlighting gig. You must make sure it doesn’t compromise your main job in terms of competition or intellectual property. Keep in mind that the more you learn, the better you can perform at your current position, as well, so choosing something that helps with that is a win-win situation.  

Transparency is key 

Say you decided to take the moonlighting job—you found it, you like it, you have the resources for it. Now it’s time to double-check your current job contract for any clauses that could prohibit taking that extra work. Also, it’s best to reach out to the HR team directly and check with them, too. That way, they are not only informed about your situation but they can take into account the new skills you might soon be able to offer. If, say, you are an IT professional looking to learn UX design via moonlighting work, you might be able to increase your standing within your primary workplace by either changing positions or taking on extra tasks to implement your new prowess—both of which should come with the financial benefits.

Summing up

Like many other seemingly passive work trends, moonlighting is here to stay—and being afraid of it is not an option. Whether you are an employer or an employee, here are the three things you should remember:

  1. Understand the company policy – most companies do not forbid moonlighting, and forbidding it is not a guarantee that it won’t happen. Rather, understand how you can work with the existing policy or, on the employer’s side, how to implement policies in such a way as to allow your employees to come to you with the information you need.
  2. Communication is key – most employers won’t mind their hires becoming more skillful, so if you want a moonlighting job for the experience, that might as well be a plus from the get-go. And if you seek extra work for extra income, your employer should have your needs in mind. Communicating your needs and goals increases not only clarity, but also trust.
  3. Master the schedule – if you work 9-to-5, you may be able to work an additional 4 hours during an evening or weekend. May is the strong word here. If you want to take a side gig, make sure it’s doable not just in theory, but in practice. And if it is, communicating and proving as much to your employer will take a weight off your shoulders. For employers, knowing that their employee is not in danger of underperforming will also solve the issue before it even starts.

Whether you see moonlighting as job cheating or a smart strategy comes down to trust, planning, and transparency. Employers and employees who work together on this can turn it into a win-win: one that develops skills, builds loyalty, and avoids burnout.

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