your next move

‘I’m Homesick. How Do I Convince My Boss to Let Me Move and Work Remote?’

A woman with cropped blonde hair and thick-rimmed black glasses stares down at a laptop computer screen. Her right hand covers her mouth in concentration.
Photo-Illustration: by The Cut; Photos: Getty Images

Dear Kimberly,

I finished law school in 2009. Because of the lasting impact of the Great Recession on the legal industry, and the fact my state has no major city (the job opportunities are not all in one place), I have moved several times in order to progress in my career. I moved in 2020 for my current job. I thought the move would be fine, since I already knew some friends in this area. However, I haven’t connected with the community and my friends aren’t as close as ones in other cities where I’ve lived. It may be that turning 40 last year has made me more reflective. I’m single with no children and no family here and it can feel very isolating. I know I don’t want to stay in this city long-term. I want to either move back to the last city I lived in or back to my hometown. Finally, after 13 years, I feel like I can commit to a city first and then work with the job situation.

I have started looking for jobs, but also want to try to get my current job to let me go fully remote. I would be no more than a three-hour drive away and could make office visits to keep connected. The company at large has embraced flexibility, but my department is traditional, with most people having very long tenures and working in the way they always have. I started during COVID and my supervisor and boss were in the office every day, so that’s what I did too. However, most of the people I interact with are actually in other offices and different time zones! Being in the office is unnecessary to my job function. When I do work from home on occasion, I’m more productive.

The boss is big on face time. I think there could also be some sensitivity that I don’t love this city like everyone else seems to. I’m usually upbeat at work and don’t say anything negative about my life, regardless of what’s going on. Would you recommend I go in and make a pitch once — as in, that’s the first time I breathe a word about not enjoying living here? Or should I build up to this? Mention some “struggles” and that I’m thinking about the future before making the formal ask? I haven’t picked a drop-dead date yet, but I do intend to eventually tell them that I will be moving regardless. I think I have good leverage, since I’m almost two years into the job, work very independently, and the department is super-busy. It would put a lot of stress on them if I left, and I know it would take 6–12 months to get someone else hired and up to anywhere near my speed. I think if I told them I was moving to get married, or because I’m having a baby and want to be near family, they would be much more receptive. But I fear because I simply don’t see this place as home and I am lonely here, that is not viewed as legitimate. There is a business case for allowing me to work remote, but I’m not sure how to approach it given people’s feelings about “how we’ve always done it.”

Thank you for any counsel,

Homesick Grown Adult

COVID-19 showed that many workers can be successful in remote-only environments, but there are still managers and companies who are excited to have their teams back in the office. Given that you were in the office during the height of the pandemic and have a more traditional boss, asking to go fully remote may be an uphill battle. While your feelings about the city you live in are valid, they may not be enough to convince your boss to allow you to work remotely if that’s not in the culture of your organization. I’m a big believer in telling the truth: It sounds like you’d genuinely like to move to be closer to your family, so that is a good starting place for the conversation.

Before speaking with your boss, check your employee manual so you are fully aware of what the company policy is on remote work. Since you plan on relocating permanently, it’s also important to note whether there are any rules about what would happen if you moved after going fully remote. Having a track record of great communication and quality work is key here as well. If you’ve been known to disappear on the days you’ve worked remotely in the past, your manager has every reason to be hesitant about letting you leave the office permanently.

In previous reader letters, I’ve mentioned preparing a one- or two-sentence statement to help keep you focused and confident in difficult career conversations. I recommend doing so in this situation too. The last thing you want to do is ramble about all the reasons why you’re fed up with your current city. Saying something similar to, “I would like to speak with you about transitioning to working remotely full-time. After two years in this city, I will be relocating back to my hometown to be closer with my family by [month, year], and I’d like to continue the great work I’ve been doing here,” gets your point across without diving into too much personal detail.

It’s important that you also propose a plan for your transition, versus simply waiting for your boss to accept or reject your ask. Going from working in the office for five days each week to being fully remote can feel like a huge leap to a manager who doesn’t approve of remote work. Suggesting a phased approach that looks like this may win them over:

Month 1: Remote Thursday–Friday

Month 2: Remote Wednesday–Friday

Month 3: Fully remote

You’ll want to propose the days of the week where your schedule is lightest as the days you plan to work remote in the early phases of the transition. For example, if you have team meetings on Tuesdays, you’ll want to continue coming into the office on that day for the first month (or more) to ensure your presence is still felt. You can also offer to have a check-in with your boss at the end of each month to ensure that your remote work is not impacting the business. If your boss is still hesitant, offering to come into the office for important stakeholder meetings could also be helpful.

If you’re truly interested in keeping your job with this company long after you move to a new city, try to determine what your boss is most nervous about when it comes to you working remotely. Maybe they’re concerned you won’t have the face time with senior management that will lead to a promotion, or they would rather stop by your office to ask you a quick question than message you on Slack. If you understand their concerns, you can tailor your proposal to make sure your boss’s needs are met.

Finally, I recommend that you continue searching for a new role while you’re advocating for remote work — especially if you know that getting your boss’s approval will take time. It’s not uncommon for there to be a process of transitioning to remote work when a company or department strongly prefers that all employees report into the office each day, so if you’re itching to move as soon as possible, landing another position in your desired city will get you there.

Career and leadership-development expert Kimberly Brown helps readers make sure their next move is the best move. Listen to the Your Next Move podcast here and keep up with Kimberly on her website.

‘I’m Homesick. How Do I Convince My Boss to Let Me Move?’