How to Work in Two Permanent Jobs Without Getting Stranded

According to recent reports from Forbes , the Wall Street Journal and Business Insider , a new trend has emerged in teleworking: keeping two full-time paid jobs simultaneously (and secretly) and getting all the benefits associated with two salaries. If you work from home in a job that requires significantly less than 40 hours of real work per week, you may be wondering if this is legal at all, and if so, how do I get it done?

No wonder it is difficult. Technically , in theory, the two permanent jobs are not illegal. But in practice it is far from easy. Here’s what you should consider before trying.

How Two Job Affects Your Taxes

Let’s start with everyone’s favorite topic: taxes. Employers withhold taxes on wages — and you pay income tax — in accordance with state law. If your new boss hires you because he thinks you are a California resident but are in fact in New Jersey, the tax departments of one or both states will have questions for everyone involved.

The coronavirus pandemic has only made matters worse. According to a detailed CPA Journal blog post on the matter , some states have temporarily decided not to tax people working for out-of-state companies if they only work from home due to the pandemic; others do not. Some of these temporary exceptions have already expired (or will expire soon), but some are valid indefinitely. This is a complete mess.

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

Is it possible that states may have conflicting regulations that create a double taxation situation for many employees? (Spoiler alert: yes.)

This applies to all teleworkers, but if you’re trying to juggle two jobs without finding out about the other, it’s important to make sure you’re not breaking tax laws in the process. If you are unsure, check with a CPA or tax attorney who knows the laws of your state (or states).

Beware of prohibitions on sharing and off-hours behavior laws.

Another thing to consider is whether your employment contracts prohibit part-time work because you will be doing it. The regulations and rules prohibiting part-time work directly restrict company employees from working outside the home. If your contract forbids you from moving to another job, and your boss still finds out that you did it, they might not just fire you – they might sue you for breach of contract.

However, as you would expect, there are exceptions. As employment attorney and author Lisa Guerin explains to Nolo.com , the content and scope of moonlight policies vary by state law. Some states prohibit employers from firing workers for (legal) off-duty, some don’t do it at all, and others only advocate certain types of behavior. “Depending on the circumstances, the off-work behavior law may limit your employer’s right to fire you for a side job, as long as it doesn’t conflict with or affect your job,” Guerin writes. It doesn’t hurt to learn a little about these laws in your area.

Bottom line: always read contracts in full before signing. If it’s too late for that, don’t take a second full-time job without carefully reviewing your “day job” contract for criticism.

What you need to know if you are a temporary employee

As you study the laws of your state, keep in mind that you can follow the rules and still get fired. Self-employment is the law of the country in almost every state in the United States, which means that many employers can fire workers for almost any reason that is not illegal or discriminatory. If, upon hearing of your second job, one of your bosses feels cheated, betrayed, or just plain angry, they can fire you for it, even if your job was exemplary.

In short, you really don’t want to be caught. If you’re serious about combining two full-time jobs, that means you can’t make a phone call. Read your contracts, know the law, and follow both to the letter – and then do both of your jobs and do them well . You can always leave or abandon one of them if the workload gets too heavy.

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