What to Ask If You Want to Relocate and Work Remotely

One silver lining of the work-from-home pandemic life is the ability to work from pretty much anywhere. And without an office or commute to tie you down, you may have wondered if living anywhere is possible, too.

Whether you’re looking for cheaper rent, an improved quality of life or even just better weather, it’s hard to deny the appeal of a change of scenery. But like any big move, there are some logistics to consider before you start packing your bags (and laptop). Here are some questions to ask if you’re looking to relocate and work remotely.

WHAT TO ASK YOUR EMPLOYER

Is my company willing to let me work remotely permanently?

If your company is planning to return to a physical office, you’ll need to find out how much remote-work flexibility they’re willing to provide. More companies have been trending toward a hybrid work situation, but if you want to live across the country, that may still not be an option for you. So reach out to your human resources department to see what the policy is. “By now, most companies will have thought through their approach and issued new guidelines,” says Tracy Cote, chief people officer at Zenefits.

If there is no clear policy, the next step is to have a conversation with your manager. “They may be more willing to accommodate a long-term, proven employee who has already been working remotely for months with success,” Cote says. But you should still be ready to sell your suggestion to your manager to improve your chances.

Will my salary be adjusted?

Some companies have announced plans to keep salaries intact for employees who choose to relocate to areas with lower costs of living, but Cote doesn’t believe this will be the case for most employers. “They will come up with their own approach to applying a geographic differential and adjust salaries to be more in line with the local cost of living and market rate for the role,” she says. Be sure to get a clear answer so there are no surprises.

What about my health care?

According to Cote, most companies offer health care plans that cover their employees in multiple locations. But if your plan doesn’t offer coverage in your intended location, your employer might be willing to pay the cost of your benefits in cash so you can secure your own coverage.

“This way, they don’t have to worry about setting up a special plan just for one person,” Cote says. “Instead, they pay you what they would have spent anyway.” But a note of caution: If your employer agrees to this, the payment could be considered income and there could be tax consequences.

Bottom line: Every company will have different policies about continuing remote work once the pandemic is over, so it’s important to be transparent about any change of residence. If you and your employer can agree on a new arrangement, be sure to get confirmation of all changes in writing.

WHAT TO ASK YOUR TAX ADVISOR

Will I have to pay taxes in multiple states?

Generally, an employee only needs to pay taxes to the state where they reside, says Dave Danic, director of tax at Summit CPA Group in Fort Wayne, Indiana. That’s because even if you live and work in two different states, many states have reciprocal agreements with their neighbors or offer tax credits that relieve you of the burden of paying taxes to your “work” state.

However, if you’re looking to move to one of the seven states (Arkansas, Connecticut, Delaware, Massachusetts, Nebraska, New York or Pennsylvania) that has a so-called convenience rule — a rule that requires workers to pay taxes in the state where their company is based — you may have to pay income tax to both your home and work states. “An employee will know if it impacts them if their W-2 form shows that taxes were withheld from the state where their company office is located,” Danic says.

Bottom line: Filing taxes as a remote worker can be complex, so consult an experienced tax preparer who has knowledge of how an out-of-state move could affect your situation.

WHAT TO ASK YOURSELF

Will remote work hinder my career?

By now you’ve probably perfected your Zoom video calls, but technology can’t always replace the value of in-person collaboration and networking. When considering your options, Cote recommends revisiting your employer’s overall outlook on remote work.

“If your company is embracing virtual work on a large scale and championing a remote-first or hybrid workforce, moving should not hurt your career trajectory,” she says. “On the other hand, if they are only willing to accommodate the occasional one-off request, moving could prove to be a little riskier from a career growth perspective, and you will want to carefully weigh the pros and cons before taking the plunge.”

It’s also smart to consider the job market in your desired area should the arrangement end up not working out as you hoped, or if you feel the need to make a change.

Does my desired location have what I need to work comfortably?

There’s a difference between visiting a place and living there. So before you relocate, make sure the area has the infrastructure you need to do remote work reliably — that cabin in the mountains might seem great until you start dropping off video calls.

Also consider life after the pandemic. Will you still love your new town when things start returning to normal? For instance, many people prefer to vary their work environment during the day, says Judy Mitchell, a real estate agent in Southport, Connecticut. “Look to see whether the new locale has coffee shops, green spaces or even a library,” she says. “Another option might be small, reasonably priced commercial offices that can provide an additional work environment close to home.”

Bottom line: Once you have a sense of what a relocation looks like on paper, do some soul-searching to ensure you're making a move that works for you in the long run, too.