🌖 How to Moonlight (legally)

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Legal Operations
Industry Insights

Side hustle, side gig, second job, passion project, an entrepreneurial venture, extra income stream. Whatever you call it, the question remains: are two jobs better than one? We cover the pros, cons, and how-tos of moonlighting as a legal professional.

Why would I want more work?

There are loads of different reasons to get yourself a side hustle. It’s an opportunity to test out a new career or try out freelancing without abandoning your day job. It could be a chance to develop specialist skills in a niche area of law that will help you in your existing role, or an outlet for a creative passion. A second job can be an insurance policy against redundancy in economically uncertain times. Plus, noble goals aside, there’s nothing wrong with a bit of extra income.

Sex, lies & videogames

But is it really doable? Hasn’t lockdown made our working hours creep further into our leisure time and pushed thousands of workers into burnout? Sure, but remote working has also revealed that either (a) working in an office involves loads of time spent pretending to be busy or (b) we can get away with doing much less work when we’re remote. Apparently, home workers have time for porn, naps, and video games during the workday (although you’re probably more likely to admit doing a load of laundry if anyone asks). And in a survey of home-workers, more than 50% admitted to working for a second company while on the clock.

Two for the price of one

You might be wondering what life as a moonlighter actually looks like. The Wall Street Journal interviewed professionals who work two full-time remote jobs and keep it a secret from their bosses. They describe playing Tetris with meeting schedules, logging into multiple calls at once, and using annual leave to make time for big projects (especially in tech jobs that offer unlimited leave). They also describe their double lives as a minefield: juggling laptops, color-coded browser tabs for different jobs, the constant fear that you’ll slip up and get caught - never mind the conundrum of what to put on your LinkedIn profile. That all sounds stressful but some of these dual-jobbers claimed they worked a 40 hour week and still doubled their salary. Tempting…

Sign me up!

If you’re going all-in with two full-time jobs, you’ll be pleased to learn that there is a website created to guide you through exactly that. But moonlighting doesn’t have to be as hardcore as a second full-time job and you don’t have to do it on the sly. In fact, it’s advisable to get your employers on board with the idea. The beauty of the gig economy is that it’s possible to take on projects of every shape and size. The first step is to choose a gig that’s well-suited to moonlighting and fits in with your primary job.

Questions to consider include:

  1. What is your primary employer’s policy on moonlighting?

Moonlighting isn’t against the law but as a legal professional, you’ll know how important it is to give your employment contract a close read. Check if your contract prohibits moonlighting or requires you to notify them if you take on other gigs. Double-jobbing might contravene non-compete or confidentiality agreements. There may be a clause that states that your employer owns your creative works - which could be a problem if you’re hustling as a screenwriter.

Some firms actually encourage employees to side hustle (sort of). Google encourages employees to spend 20% of their time exploring anything they think could benefit Google and Infusionsoft encourages employees to start a small side business. You might have more success persuading your employer to let you take on a side gig if you can show how they can benefit from your new skills and experience.

  1. What kind of company should you look for?

It might be strategic to look for a second employer with flexible hours or even one based in a different time zone.  Overemployed suggests checking Glassdoor reviews to get an idea of how much engagement a company will expect of you. If you get through to the interview stage, it’s worth discussing things like workflow and meeting commitments.

  1. Should your second job be in law?


Working a second job in law means you can leverage your existing skills to maximize your income. Jumping from job to job will be less of a mindset shift. Plus freelance legal jobs are an opportunity to gain specialized experience. However, sticking to the same field creates space for conflicts of interest, and (if you’re on the sly) it could increase your risk of getting caught.

It might be wise to pick a second gig that fits so neatly with your skillset and experience, you can do it in your sleep. That way you don’t have to worry about mastering something new and you can tackle it even when you’re a bit worn out from your primary role.

  1. How will you manage your time?

Decide if you’re an early bird who can fit in a few hours before work, a multi-tasker who can squeeze things in during the workday, or a person who needs time to sink into a task. If you fall into that last category, you could look at using your weekends and annual leave for your side gig. It isn’t ideal for your work-life balance but it might be the most feasible way to fit it all in. Alternatively, if your primary employer is flexible, you could pair a four-day week with a day for your second job. If you’re unsure about how it will all work, consider taking on a short-term project as a trial.

There are also tools that can help you boost your productivity and manage your time. Mondays is a workflow solution that helps you visualize your to-do list, collaborate efficiently, and even automate routine tasks. RescueTime is another helpful tool. The app blocks distractions and tracks how much time you spend on different things, so you can avoid time-wasting and schedule time for tasks.

Blame it on the moonlight

Before you commit, there are a few other potential pitfalls you should be aware of. While some moonlighters can fit two jobs into a standard working week, that’s not always the case. Working too many hours can jeopardize the quality of your work and endanger your health. It might also put your employer in breach of working time regulations which limit the hours employees can work in a week. These rules vary in different countries.

Gone are the days of climbing the ladder at one company from graduation to retirement. The modern world of work is filled with possibilities. After lockdowns shook-up office culture, companies are grappling with the future of work. New working cultures are starting to be solidified in company policy. And after record numbers of workers quit their jobs in what’s being called The Great Resignation, now is the time to negotiate working arrangements that let you explore the opportunities available. Maybe ‘moonlighting’ isn’t such a dirty word after all.

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