'How Can I Convince My Boss to Let Me Work From Home Forever?'

I'm a young professional who works with a major company making a very good salary for my area and age. I'm very lucky to have gotten this job, and I don't want to leave it anytime soon. 

Due to life circumstances I still live with my parents, and I haven't gotten enough savings yet to move out on my own, even aside from the Covid situation. However, my parents are planning on moving within the year to another city. 

I'm currently working from home due to the pandemic, but it's been made clear that that's not going to be forever. Would it be weird to ask to keep working from home if/when the move occurs? I haven't been working for the company for very long, but I've gotten good feedback from upper management and my team, so I'm pretty sure they would want me to stay if they could swing it. I'm pretty bad at advocating for myself at the best of times, so I'm not even sure how to approach this.

You have a lot of company in grappling with this right now! Some people have realized they simply prefer working from home and are more productive without the distractions of the office. Others have realized they could move somewhere they’d prefer to live (often somewhere more affordable or near family) while still keeping their jobs. And all of them, like you, are wondering how to broach the possibility with their employers. 

Fortunately, once pandemic restrictions ease it’s likely that many employers will be more open to remote work than they have been in the past. This past year has been a massive, involuntary experiment in working from home, and it’s turned out to be more workable than a lot of employers thought—meaning they’re likely to be more open to requests like this. But other employers are eager to get people back in the office once it’s safe to do. Sometimes that’s for legitimate reasons (some work genuinely is harder to do if people aren’t in the same location) and sometimes it’s just philosophical opposition to having staff working from home. So there’s no guarantee that any given employer will agree to it, but it’s become such a normal part of the national conversation right now that it won’t be terribly weird to ask about it.

Generally the way to raise the question is to say something like, “I’ve been really pleased with how working from home is going. I find my productivity is up, it’s easier to focus, and the systems we’ve put in place are working really well. Would you be open to talking about me continuing to work from home even after we reopen? I’d love to move to NewCity if there were a way for me to stay on the team while living there.” If you’re a strong employee who’s built up some political capital and good will, a good manager should at least give the request real consideration—and ideally should realize it’s a way to retain a good employee. (Note that at this stage you should not say your plans to move are a sure thing unless you’d be OK with your employer telling you that won’t work on their end, so good luck and goodbye.)

In your case in particular, it’s OK to say that you’re considering moving to stay near family, but I wouldn’t explain that it’s so you can continue living with your parents. There’s nothing wrong with living with your parents, but you risk your manager thinking, Why can’t you just get housing of your own instead of expecting the company to make this exception for you? That’s not necessarily fair or reasonable—particularly because that response isn’t likely if you were moving to be with a significant other—but our culture has some odd baggage around living with parents.

Something else to know is that it can be more complicated for your employer to let you work from another state than people often realize. If they’re not already set up to do business in that state, having an employee working there can mean they have to charge sales tax to customers there, as well as pay taxes to that state. They’d also need to buy worker comp insurance there and comply with the new state’s labor laws, which might be more restrictive than the ones they’re used to. That doesn’t mean they won’t do it, but be aware it’s not always as easy as “sure, move wherever you want.”

One last thing: If you weren’t asking about moving to a new city but just wanted to keep working from home after things reopen, I’d tell you to consider proposing a hybrid model where you work from home X number of days per week and are in the office the other days. That’s often easier for employers to agree to, and it can get you some of the benefits of each approach: you still get to skip the commute and work in sweats without interruptions some of the time, but you also get the face time and easier collaboration that being on-site can provide.

Get more good advice from Alison Green at Ask a Manager or in her book. Do you have a pressing work-related question of your own? Submit it using this form.