Negotiating Working Abroad or Sabbaticals With Your Boss

Now might be the best time ever to start negotiating working abroad or taking a sabbatical. Last week I had a meeting with my two bosses (director and VP) going over this. That meeting ended with approval for me to work abroad for two weeks in June. Still being able to work from a whole ‘nother continent is how I can manage to go visit Europe for an entire month.

I’ll first write about how I got my bosses to agree to this when there’s a big push to get everyone back in the office. Then I’ll write about what will most likely will and won’t work for you, dear reader, in your own negotiations. Whether you’re negotiating working abroad or getting a sabbatical, planning will make it much more likely they’ll say “yes”.

How I Negotiated Working Remotely Abroad

Going to Europe for an extended time has been on my radar for ages. I originally wanted to go after hitting a net worth goal last year; that wouldn’t have been advisable with COVID still raging. Instead I hung tight and looked forward to 2022, when I could finally start making these plans to go. Because my friend “Bee” is graduating with her Master’s from a London school in late May, I started planning for a concrete date of being there for her.

Fast forward to early March, when we were back in the office for the first time in months. I unintentionally gave my two bosses a surprise when I mentioned I was thinking about working abroad for a month (meaning 2 weeks of vacation plus 4 weeks remote). Both were startled as I belatedly realized this was the first time they were hearing about my plans…

I quickly backtracked and said I’d send a proper request soon… whoops. Despite embarrassing myself a little, I’m glad I brought it up that way; it helped me gauge how doable something like that was. Based on their reactions, I decided to formally request I work abroad for 2 weeks instead.

This additionally worked because a member of our team revealed that same day he and his wife were expecting; their due date in early July. That makes for a great reason to say why I was shortening the request from 4 weeks to 2, so I can help cover once he’ll take paternity leave.

The Prep

This is where my being friendly with lots of other folks in the company came in handy. I knew of two other people who had worked abroad in the last year. That means there’s a precedent I can lean on for what I want to do. One is on my company team and worked from Central America for a month last year. The other coworker is from a different department and worked abroad from her home country for two months. I reached out to both of them asking for help with this message:

Hey, hope all is well! I remember being in a meeting with you while you were first in [Country], and I’d like to do something similar later this year (but working from Europe instead).  I was wondering if I could send you some questions about working remotely abroad for a certain amount of time?

Both were AMAZING at answering my questions and excited to help right then and there! Some of my questions to them included:

• How long were you working abroad? What steps did you take to get that arrangement set up with the company?
• With all of the security the IT team has set up, was working from a foreign IP address ever an issue?
• Were there any formalities you worked through with the company? Like paperwork or if you couldn’t work more than X number of days abroad.

After chatting more with my team member I learned one of my bosses was originally nervous about the time zone differences, which I accounted for in my ask. The different-department coworker went a step further and generously sent me the email of HER request to work abroad; in hers she specified she’d still work East Coast hours, which I shamelessly borrowed for my own.

The Ask

Using my coworkers’ input, I sent my VP (“Bossman”) an email as follows:

There are a couple of things I want to highlight here. First, I made sure to mention there were two other coworkers who have done what I want to do. Second, I made the ask as flexible and streamlined as possible. I gave two different time frames on the off-chance one worked better than the other. I also made it a point to say I’d be on the clock 9am-5pm EST, so no time zone kerfuffles with my plans.

Bossman responded to my email a few days later with a request to set up a meeting about this. He also had two follow-up questions: Would I be working primarily from a hotel, a rental apartment, or an Internet café? “Because an ‘internet cafe’ would be problematic for more than a little bit of time” (his words.) Also, am I planning a week in each country and traveling over the weekend?

Easy answers as I scheduled a Zoom meeting and nervously waited until we could chat. Once I got on the call with Bossman and Director, they brought up a couple of concerns and points before saying “ultimately, we don’t have a problem with you working abroad for two weeks”. That sentence was followed by “especially since you originally said four weeks,” so my slight blunder ended up helping me further. I excitedly thanked them, got off the call, and did a little victory screech in the confines of my apartment.

I. Am. Going. To. Europe.

What Works in Your Favor

It’s really exciting to consider the possibility of traveling while working, albeit temporarily, to maximize your times for adventure. Being in your 20s makes it a phenomenal time to travel. Even better, 2022 might be the best time to go in negotiating working abroad or sabbaticals. Specifically, because of the Great Resignation still in full effect. Depending on your position, it likely costs a company thousands of dollars to hire someone else to fill your role if you choose to resign. Keeping you happy (and employed) is more of a priority now than ever. Plus, pointing out you’ve worked remotely for 2+ years now sure won’t hurt your cause.

That said, the trust your boss has for you also plays a large role. Both of my bosses know my work ethic and that I’m quick to ask for help if I need it. Because they trust me and my capabilities, they don’t have doubt about my abilities working remotely abroad, either. If I sucked as an employee, and then asked to work overseas for any amount of time, I’m not sure this would have been approved.

Finally, it’s a requirement to show you’ve prepared and to set expectations. Depending on the bureaucracy in your workplace, you may have proposals, HR forms, and other paperwork to fill out in order to begin negotiating working abroad/a sabbatical. “I’m going to work abroad on these dates, Bossman, see ya” is not going to cut it. Keep communication lines open and show you’ve planned this all out. Also, be prompt about answering questions over things like your WiFi connectivity or contingency plans.

What May Work Against You

As I had mentioned in my previous post, this wasn’t a straightforward sell to my bosses. The biggest reason it wasn’t automatically approved was due to our company’s back-to-office insistence. I’m getting the impression the executive team is insisting on VPs forcing employees back into the office. I genuinely believe my direct bosses are trying to please the execs while also giving me and my teammates as much flexibility as possible. Due to that, me not being in the office at all for 2 weeks is not ideal from that angle. Keep your finger on the pulse as to what your own company leadership is pushing for. At best, you can mitigate issues if your execs similarly want butts in office seats.

If the main issue isn’t over physically working in an office, it’s going to be over bad timing. Be honest: would negotiating working abroad or taking a sabbatical coincide with a huge project? If so, that’s going to make your boss hesitate on saying “yes” to your request. If you’re thousands of miles away with limited availability – or worse, unavailable at all – that could quickly morph into a logistical nightmare as your boss scrambles to find coverage, manage your workload, and satisfy coworkers frustrated you’re AWOL at such a crucial time. These concerns are exactly why I timed my trip to a very quiet time of year work-wise. No issue with missing important deadlines if there aren’t important deadlines to miss.

Openness and Honesty is Crucial

There’s always going to be a reason you want to negotiate working abroad or taking a sabbatical. In my case, one of my best friends is graduating with her Master’s degree from a university in London. I will be the only person from the States who will be going out to support her – not because other family and friends aren’t eager to, but because I’m the only one both eager and able.

A fellow coworker managed to work abroad for roughly two months because she had to go back anyway to renew her work visa. Both are excellent reasons for requesting to go abroad (with the visa renewal being a much better reason than mine!) but you don’t strictly need a reason like that make your request. If you worry you need a “legitimate” reason to request work abroad or a sabbatical, you have my permission to desire one because you want to.

Again, the key is openness and honesty.

Frame it as a benefit to both yourself AND your employer. “I’d like to take some time to relax so I can come back refreshed and ready for anything” is a totally valid explanation. Humans aren’t machines; our bodies have a hard requirement for rest. Taking the time to rest and reset is totally good. So is taking the time for other life events like healing from a breakup, divorce, or a loved one’s passing. Whatever your reasons are, they are valid ones.

So answer questions or concerns before your management can voice them, as long as they’re not prying into protected topics like your medical record. Your answers will show you’ve been planning and smart about this instead of showing nothing but arrogance over “I’ll have it covered, dude trust me”. Being fully open and honest will make the request process so much smoother and more streamlined.

Helpful Tips for Negotiating Working Abroad

When you’re ready to start negotiating working abroad, one of your first tasks is working out when your work hours will be. For me, I planned to work regular East Coast hours to both make it easy on everyone else and hard for management to say no. 9-5 EST will be 3pm-11pm in the European time zones I’ll be in. That’s not an issue for me; it’s essentially working second shift at the end of the day. Besides, I’ll get plenty of time in the morning and early afternoon for other stuff.

During your ask, reassure them of your availability and WiFi access. I’ll be working from Nordic countries with some of the best Internet on the planet, but you might be going to a country with known connectivity issues. Are you staying in a hotel that prioritizes online access? Do you have a fancy way to connect to the Internet via satellite? Be completely transparent about this to allay any worries you’ll be unreachable in the Tasmanian jungle.

Helpful Tips for Negotiating a Sabbatical

If I had planned to take a sabbatical instead for those 4 weeks, that would be a much different ask but would ultimately see me go through a very similar process.

First things first: have your “why” ready and how it benefits the company as well as yourself. Companies are greedy bastards by nature and pesky things like “empathy” and “decent work/life balance” are exceptions to the rule. As a result, frame you taking a sabbatical as a way for you to refresh and recharge to come back stronger than ever. If your boss has more than two brain cells to rub together, they’re going to recognize you taking a sabbatical and returning is much cheaper than you quitting and making them find someone new.

Keep in mind, too, sabbaticals are a harder sell if you’re in a low-paying job or in your 20s. Work culture in America is fucked and taking multiple weeks off from work is not a cultural norm. Further complications from jerk bosses who might tell you to your face you haven’t pAiD yOuR dUeS enough to take it or some other BS.

So have a backup plan if your boss says no to a sabbatical.

Don’t give them the satisfaction of watching you drop the subject and walk dejectedly back to your desk. Thank them, ask what it will take for them to reconsider. There’s always the nuclear option of straight-up quitting. Be prepared for if they say yes, and be prepared for if they say no.

Finally, I cannot say enough good things about the FIRE movement. Including the sheer amount of resources FIRE people give to everyone else for free.

The financial independence forums have been covering taking sabbaticals since 2016. For more updated guides on sabbaticals, I highly recommend reading The Fioneers and their advice or doing a few Google searches about mini-retirements on the path to FIRE. A little bit of reading will go a very long way in negotiating working abroad or your sabbatical.

Are you planning on negotiating working abroad or taking extended time off? I’d love to hear about it and share your story! We need more Americans to push for flexible work opportunities like this. In what (possibly? Hopefully?) looks like a post-COVID world, anything to help worker’s rights will help more than just you in the long run.

Cover image credit: Crew via Unsplash