ask a boss

‘I Want to Keep Working Remotely Forever’

Photo-Illustration: by The Cut; Photos: Getty Images

Dear Boss,

I am in a low-paying industry that is concentrated in high-cost-of-living areas, which means that it’s virtually impossible for me to live without roommates unless I want to spend nearly all of my monthly income on rent (which I obviously don’t). There are jobs in my industry in other locations, but significantly fewer, and the few that exist have less job security because they are generally smaller, less stable companies. 

My job has its issues, but ultimately I’d like to stay with this company for the foreseeable future. The problem is, I am becoming increasingly unhappy living where I am. Maybe it’s the pandemic talking and I’m just missing being able to take advantage of the things that make city living exciting (museums, theater, excellent restaurants, etc.), but I’m tired of how expensive it is to live here. I want to have my own apartment and live in a place that feels like home. I like my roommates, but I’m in my late 20s and want to feel more adult and have my own space. Ideally, I’d love to keep my job but move to a completely different location and work remotely.

I’ve already been working from home for the past year because of COVID. My company has adapted quite well to remote work and we haven’t had many major difficulties. 

Because they’ve responded so well to this change, I think the chances of them allowing me to move to permanent remote work is higher than it would have been at this time last year. We have a bit of a precedent for full-time remote workers from before the pandemic — one manager in my department has worked remotely for several years, as does another co-worker who is at my level of seniority but in a different department (she moved and went fully remote during the pandemic). 

Both of these co-workers were approved to work fully remote because their partners got jobs out of state. I don’t have that clear-cut reason. If I were to talk to my manager about the possibility of moving and being permanently remote, how would I justify it? Tell them I want to be closer to my family? Say that living here is negatively affecting my mental health? Both of those are true, but I don’t know if my boss will see them as valid reasons to move out of state and work remote permanently. Is it even worth trying? 

Give it a shot!

A lot of companies have become much more open to remote work than they were before the pandemic — sometimes because they’ve seen it work well, sometimes because they’ve realized they can save money by not having as many people on-site, and sometimes because they’re concluding they’ll have to remain remote-work-friendly if they want to attract and retain good employees.

Of course, that’s not true everywhere. Lots of companies are eager to bring everyone back once they can do it safely (and some are eager to bring everyone back before it’s safe). That can be because they were always philosophically opposed to remote work and the pandemic didn’t change that, but sometimes it’s because their work really can’t be done as effectively without people on-site.

But raising the question is a reasonable thing to do, and it’s a conversation that a lot of people are having right now (or are planning to have). You might not get a “yes,” but there’s nothing outrageous about asking.

One thing to be aware of, since you’re asking not just to continue working from home but also to move out of state: It can be more complicated than people often realize for your employer to let you work from another state. If they’re not already set up to do business in that state, having you work there creates what’s called “nexus,” which can have significant financial and logistical implications for them. They would need to pay taxes and buy workers’ compensation insurance there, might need to charge sales tax to customers in that state, and would need to comply with local labor laws, which might be different from the ones they’re used to. (That could mean anything from having to display different information on your pay stub to owing you overtime pay in more situations, depending on the state.) That doesn’t mean your employer won’t be willing to do it — some are — but know going in that it’s not necessarily as straightforward as people often assume it is.

As for how to ask, you’re right that it’s often easier if you have a clear-cut, easily explainable need to move, like a partner who got a job somewhere else or even family you’d like to be closer to. When it’s more general quality-of-life reasons — a lower cost of living, a town you simply prefer, or so forth — it can be a harder sell. But that doesn’t mean it’s an impossible one; you just need to think about how to frame it.

One way to present it is to talk about how keeping you remote would benefit your employer. If you’ve been more productive working from home because you can focus better, mention that (and if you can quantify that with concrete metrics, even better). If it’s allowed you to be more flexible in ways that benefited your team (like if you’ve been more able to jump on and resolve a work crisis in the evening because all your work stuff is with you), mention that.

But maybe there’s nothing like that you can point to. Still, if staying remote would keep you loyal and happy and retain you long-term, that’s worth explicitly mentioning if you know your employer really values you and is motivated to keep you from leaving. The more valued you are and the less your manager wants to lose you, the more persuasive this is likely to be.

If none of that feels like the right framing, you may need to just ask. For example: “I’ve been really happy with how well working from home has gone, for me personally and for the team. Would you be open to talking about me continuing to work remotely after we reopen? I love my job, but I’d like to be able to move to a lower-cost-of-living area at some point, and after seeing how well this year went, I’m hoping there’s a way to do that while still keeping my job.” (Note that this language doesn’t say you are moving; keep it in the realm of the hypothetical at this stage so that they don’t interpret this as you resigning!)

Ultimately, your employer may or may not okay your request. But it’s a reasonable conversation to have, and one that’s going to be happening at a lot of workplaces this year.

Order Alison Green’s book Ask a Manager: Clueless Colleagues, Lunch-Stealing Bosses, and the Rest of Your Life at Work here. Got a question for her? Email Her advice column appears here every Tuesday.

‘I Want to Keep Working Remotely Forever’