cartoon gunslinger cowboys facing each other The notion of employees working all over the country or around the world could create a Wild West scenario for HR when it comes to tax compliance. (Photo: Shutterstock)

Airbnb CEO Brian Chesky made headlines recently when he announced he’d be spending the next year moving from city to city every two weeks living and working in Airbnb properties. This sounds like a digital nomad’s dream, and technically it’s entirely feasible. But the first thing that came to mind is, “I wonder if HR is freaking out? This could be a compliance nightmare if they’re not prepared.”

While living in a new city every two weeks probably isn’t a realistic scenario for many employees, it underscores the possibilities that remote work affords. Employees have made it abundantly clear that flexibility to work anywhere they choose is a top priority. And as long as they’re remaining productive and engaged, employers have little choice but to extend the opportunity—otherwise they risk losing great talent.

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