How to Work Two Full-Time Jobs Without Getting in Trouble

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According to recent reports from Forbes, the Wall Street Journal, and Business Insider, there’s a new trend in remote work: Simultaneously (and secretly) holding down two full-time, salaried jobs—and enjoying all the perks that come with two salaries. If you work from home at a job that requires significantly less than 40 hours of real work per week, you may be wondering: Is this even legal, and if it is, how do I pull it off?

Unsurprisingly, it’s complicated. Technically, in theory, holding down two full-time jobs isn’t illegal. But in practice, it’s anything but straightforward. Here’s what you should consider before giving it a shot.

How working two jobs impacts your taxes

Let’s start with everyone’s favorite topic: taxes. Employers withhold payroll taxes—and you pay income taxes—according to state laws. If your new boss hired you under the assumption that you’re a California resident but you’re actually in New Jersey, one or both states’ revenue departments will have some questions for everyone involved.

The coronavirus pandemic has only made everything more complicated. According to a detailed CPA Journal blog post on the subject, some states have temporarily decided not to tax people working for out-of-state companies if they’re only working from home because of the pandemic; others have not. Some of those temporary exemptions have already expired (or will soon), but some are indefinite. It’s a whole mess.

So what does all this mean for you? Maybe nothing—but maybe something bad. Here’s how the CPA Journal put it:

Is it possible that states could have contradictory rules, creating a double tax situation for many employees? (Spoiler alert: yes.)

This applies to all remote workers, but if you’re trying to juggle two jobs without either finding out about the other, it’s extra important to make sure you’re not unwittingly violating tax law in the process. If you’re not sure, consult a CPA or tax attorney who knows the law in your state (or states).

Beware of anti-moonlighting clauses and off-duty conduct laws

Another thing to consider is whether your employment contracts explicitly forbid moonlighting, because that’s what you’ll be doing. Anti-moonlighting clauses and policies specifically restrict a company’s employees from taking on outside work. If your contract bars you from taking another job and your boss finds out you did it anyway, they might not just fire you—they could sue you for breach of contract.

As you might expect, though, there are exceptions. As employment attorney and author Lisa Guerin explains for Nolo.com, the content and reach of anti-moonlighting policies depend on state laws. Some states prohibit employers from firing workers for (legal) off-duty activities, some don’t at all, and others only protect certain types of conduct. “Depending on the circumstances, an off-duty conduct law might limit your employer’s right to fire you for moonlighting, unless it conflicts with or affects your work,” Guerin writes. It can’t hurt to learn a little bit about these laws in your area.

The bottom line: Always read contracts in full before signing. If it’s too late for that, don’t accept a second full-time gig without thoroughly reviewing your “day job” contract for anti-moonlighting language.

What to know if you’re an at-will employee

As you research your state’s laws, keep in mind that you can follow the rules and still get fired. At-will employment is the law of the land in almost every U.S. state, which means many employers can dismiss workers for almost any reason that isn’t illegal or discriminatory. If learning about your second job makes either of your bosses feel deceived, betrayed, or just plain pissed off, they can fire you for it—even if your performance has been exemplary.

In so many words, you really don’t want to get caught. If you’re serious about juggling two full-time jobs, this means you can’t phone it in. Read your contracts, know the law, and follow both to the letter—then do both of your jobs, and do them well. You can always quit or resign from one if the workload gets too intense.

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