Over Thanksgiving, I did something novel (at least for me): I painted my home office space.

That, of course, led to the realization that the carpet was hopelessly outdated and, since we were at it, the light fixture was falling apart, and the desk and chair I was working from for the last 9 months were not conducive to 12 hour workdays.

And so, over the course of the last week, we replaced them all.  (Used office furniture now is really cheap.)  If I’m going to be working from home for the forseeable future, it might as well be comfortable.

Working from home SHOULD be comfortable. Yet for companies who are trying to accommodate employees (and the government) with working from home, they are coming across a hard reality – our modern employment laws are hopelessly dated when it comes to remote workers.

This is an uncomfortable place for employers to be.

Suppose you’re a Connecticut employer with an employee who has now been forced to work remotely.  Rather than be cooped up in an apartment, the employee has decided to rent a slopeside condo in the Lake Tahoe area.  Work never looked so good.

But does it?

What laws apply to that employee? Connecticut? California? Both?

What tax issues arise? Should the employer be withholding California taxes? Should the employer be registering as a business in California?

Does an employer have an obligation to pay for expenses for an employee working remotely? What about if they’re working in a state that may otherwise demand it?

An article Friday evening by Politico highlighted this absolute mess. The headline? “Congress struggles to fix tax mess caused by people working from home”.  

Complicating the issue further is the fact that certain states, like New York, are “notoriously aggressive about taxing people coming to the Empire State even temporarily”.

These are challenging questions — ones that can’t really be answered quickly by a blog post unfortunately.

But employers that have a workforce that has gone really remote ought to be considering all of these implications as weeks turn into months, and months turn into a year (or two or three?).

In the meantime, you know where you can find me? My home office in Connecticut. Though that ski house does sound awfully attractive….

Stay safe everyone.