Working vacations
August 22, 2022 1:04 PM Subscribe
I am planning some travel next year (maybe Greece?) and I'm thinking it might be fun to go for a whole month - take a week or two off for a real vacation, then rent an apartment somewhere and work remotely for the rest of the time, perhaps with long weekends for some side trips. My job has West Coast hours but I could probably get away with East Coast hours, basically working in the evenings. I'm curious if others have traveled like this before. Is it enjoyable/worth it? Any potential problems that I'm not thinking of?
I'm doing this with my wife right now! Not as fancy as Greece, but we're renting a house in her home town this week and then next week we're doing the same with my home town. By day we work and then visit family in the evenings.
It's been strangely relaxing even though our hours are the same. Something about getting out of the usual surroundings and routine I expect.
We were able to drive to our destinations, so we brought along full size mice, keyboards and monitors. That's a luxury, but I think it would be fine without too.
posted by Eddie Mars at 1:08 PM on August 22, 2022
It's been strangely relaxing even though our hours are the same. Something about getting out of the usual surroundings and routine I expect.
We were able to drive to our destinations, so we brought along full size mice, keyboards and monitors. That's a luxury, but I think it would be fine without too.
posted by Eddie Mars at 1:08 PM on August 22, 2022
You need to make sure the country you are working in allows this in addition to your own company. Greece, for example, seems like it would require to get a work visa to do this because Schengen visas do not allow for employment.
posted by soelo at 1:13 PM on August 22, 2022 [1 favorite]
posted by soelo at 1:13 PM on August 22, 2022 [1 favorite]
Also, do you do something that involves words like "export control"? I ask because even people who know they do ask to do this in my company all the time.
posted by atomicstone at 1:17 PM on August 22, 2022
posted by atomicstone at 1:17 PM on August 22, 2022
When done at length, the term for this currently is "digital nomad". It is actually pretty fraught when it's international for tax and business permit/licensing reasons (as in your employer could get in deep shit with some other country's ministry of business/employment/accounting), but if it's only for a shorter period of time (and likely wrapped in some PTO) you can sometimes get a green light from your employer, and if you present yourself on entry/at immigration simply as a person who is on vacation but has to be reachable by their employer because that is the American Way but definitely not working-working, you may be able to make this happen.
While my fully-remote employer doesn't especially care where in the US we are, we can't take our equipment out of the US for security reasons and aren't allowed to access any company systems except email/calendar and Slack from outside the US on personal devices either. This is in part because some of our customers require us to maintain that kind of security if we're going to ever access their systems. These are not customers one should fuck with. If you intend to do this in stealth mode, know that you may have (unbeknownst to you, in small print you didn't read) signed something agreeing to not do this for any of the above reasons or others, and yes IT departments absolutely can catch you even if you think you are covering your tracks.
My partner and I are about to do this within the US, and I already know this isn't going to be quite as easy as having A Home Office that is relatively unchanging and does not need to be dismantled and reset on a regular basis. I've fully disclosed the plan but am still being pretty low-key about it to all but my closest colleagues, because there's absolutely a sentiment that someone who is enjoying where they're staying too much isn't spiritually fully engaged in the daily slog of work, but it's fine if they live there permanently for some reason.
posted by Lyn Never at 1:32 PM on August 22, 2022 [1 favorite]
While my fully-remote employer doesn't especially care where in the US we are, we can't take our equipment out of the US for security reasons and aren't allowed to access any company systems except email/calendar and Slack from outside the US on personal devices either. This is in part because some of our customers require us to maintain that kind of security if we're going to ever access their systems. These are not customers one should fuck with. If you intend to do this in stealth mode, know that you may have (unbeknownst to you, in small print you didn't read) signed something agreeing to not do this for any of the above reasons or others, and yes IT departments absolutely can catch you even if you think you are covering your tracks.
My partner and I are about to do this within the US, and I already know this isn't going to be quite as easy as having A Home Office that is relatively unchanging and does not need to be dismantled and reset on a regular basis. I've fully disclosed the plan but am still being pretty low-key about it to all but my closest colleagues, because there's absolutely a sentiment that someone who is enjoying where they're staying too much isn't spiritually fully engaged in the daily slog of work, but it's fine if they live there permanently for some reason.
posted by Lyn Never at 1:32 PM on August 22, 2022 [1 favorite]
I'm doing this now, and have done it quite a bit over the last 7 years due to remote work flexibility. If you're a night owl and can work East Coast hours, Europe and the UK work really well for this: museum/stroll/beach/whatever until 2 or 3 PM, then sign on for work.
For US based versions, we often team up with friends, and pick a place with nice lodging and scenery, but less attractions, and just make it cozy and calm.
The main thing I've learned is to avoid picking places that have too much STUFF to do, where you'll regret missing out. I've felt best when picking places I know I can easily go back to if I want, so FOMO is minimized.
Random tips: if you're in Europe, going out to dinner is hard with work hours, I try to self cater. Also set your Slack time zone to your normal time zone, not determined by your location, otherwise you'll spend a lot of time explaining why it says it's 11 pm and yes it's ok to chat. If you're planning to see local friends in Europe, and they work 9-5s, you're limited to weekends.
Also avoid doing it during busy or important work periods - motivation to put in extra hours is low, and unexpected internet issues can be a nightmare for important calls.
(Also yes, make sure your company allows it, read the handbook. Smaller/newer companies often don't have it together enough to have a policy against it.)
posted by soleiluna at 1:52 PM on August 22, 2022 [2 favorites]
For US based versions, we often team up with friends, and pick a place with nice lodging and scenery, but less attractions, and just make it cozy and calm.
The main thing I've learned is to avoid picking places that have too much STUFF to do, where you'll regret missing out. I've felt best when picking places I know I can easily go back to if I want, so FOMO is minimized.
Random tips: if you're in Europe, going out to dinner is hard with work hours, I try to self cater. Also set your Slack time zone to your normal time zone, not determined by your location, otherwise you'll spend a lot of time explaining why it says it's 11 pm and yes it's ok to chat. If you're planning to see local friends in Europe, and they work 9-5s, you're limited to weekends.
Also avoid doing it during busy or important work periods - motivation to put in extra hours is low, and unexpected internet issues can be a nightmare for important calls.
(Also yes, make sure your company allows it, read the handbook. Smaller/newer companies often don't have it together enough to have a policy against it.)
posted by soleiluna at 1:52 PM on August 22, 2022 [2 favorites]
Just got back from 2 months of this (with 1 week fully off in there) - it's great! I've now done this about 4 times, 1-2 months each time. My tips:
- Unpredictable internet is a big issue at times. It's best to have an unlocked phone where you can buy a local sim card, and then do a wifi hotspot from the phone to then work off of. This is super affordable in europe, usually there will be a 30 day sim card that has 15-30GB for 10-20 euros. It saved me several times when hotel wifi didn't work and we would have had to change
- If you're traveling within europe try to make your travel days weekends. It feels like a big sacrifice of free time, but it's better than dealing with airport delays AND not making it to your meetings. If you're driving or taking trains in relatively punctual regions, weekday travel is fine.
- At least once or twice a week, allow yourself to take a long dinner break and do zero or the bare minimum afterwards. Long european dinners (esp with friends) are lovely!
- With coworkers, don't lie about where you are but also kinda downplay how much fun you're having. Stick to the topic at hand and people will mostly forget you're even away.
- Skip any nice-to-have type work / meetings - team building, etc. Be okay doing the bare minimum and focus on delivering what you need to deliver
- You can have a big night Sunday night since you don't need to be functional until like 4pm Monday - take advantage!
- Some of your time will be spent on boring life stuff like figuring out where to do laundry in a small beach town. It will take way longer than at home and it will feel like an incredible accomplishment to figure it out. Budget extra laundry time in particular since people tend not to have dryers there
- It's pretty hard to keep a workout routine going but try to stay active with the activities you're doing as a tourist (hikes, swims, etc.) If you're visiting a town with a local friend, see if you can be a gym guest for a day for free, etc.
posted by internet of pillows at 2:21 PM on August 22, 2022 [4 favorites]
- Unpredictable internet is a big issue at times. It's best to have an unlocked phone where you can buy a local sim card, and then do a wifi hotspot from the phone to then work off of. This is super affordable in europe, usually there will be a 30 day sim card that has 15-30GB for 10-20 euros. It saved me several times when hotel wifi didn't work and we would have had to change
- If you're traveling within europe try to make your travel days weekends. It feels like a big sacrifice of free time, but it's better than dealing with airport delays AND not making it to your meetings. If you're driving or taking trains in relatively punctual regions, weekday travel is fine.
- At least once or twice a week, allow yourself to take a long dinner break and do zero or the bare minimum afterwards. Long european dinners (esp with friends) are lovely!
- With coworkers, don't lie about where you are but also kinda downplay how much fun you're having. Stick to the topic at hand and people will mostly forget you're even away.
- Skip any nice-to-have type work / meetings - team building, etc. Be okay doing the bare minimum and focus on delivering what you need to deliver
- You can have a big night Sunday night since you don't need to be functional until like 4pm Monday - take advantage!
- Some of your time will be spent on boring life stuff like figuring out where to do laundry in a small beach town. It will take way longer than at home and it will feel like an incredible accomplishment to figure it out. Budget extra laundry time in particular since people tend not to have dryers there
- It's pretty hard to keep a workout routine going but try to stay active with the activities you're doing as a tourist (hikes, swims, etc.) If you're visiting a town with a local friend, see if you can be a gym guest for a day for free, etc.
posted by internet of pillows at 2:21 PM on August 22, 2022 [4 favorites]
I have done this and my coworkers have done this, but under the radar (our managers knew, but no one was reporting this to HR). Pretty sure we wouldn't have been officially allowed to do it because of the tax problems everyone has mentioned above. I've also done it repeatedly in the U.S., and technically that has state tax implications here, but again, I didn't officially report it was happening. Is it fun: yes.
posted by pinochiette at 2:24 PM on August 22, 2022 [1 favorite]
posted by pinochiette at 2:24 PM on August 22, 2022 [1 favorite]
I did this for about five years leading up to the start of the pandemic, with trips ranging from 4 to 6 weeks long. It’s such a great way to travel! I typically averaged working about 50% my normal work day during that period. Some days I didn’t work at all when I wanted to do more time/energy consuming activities and I worked more on days with bad weather, for example.
I found it takes away that feeling that you Must Jam Pack Every Minute With Activity!!!! feeling that you get on shorter trips and allows for much more ebb and flow to do things depending on your energy level. I also find it lets you experience a place more like a local.
Definitely my preferred way to travel now!
posted by bkpiano at 7:52 PM on August 22, 2022
I found it takes away that feeling that you Must Jam Pack Every Minute With Activity!!!! feeling that you get on shorter trips and allows for much more ebb and flow to do things depending on your energy level. I also find it lets you experience a place more like a local.
Definitely my preferred way to travel now!
posted by bkpiano at 7:52 PM on August 22, 2022
I recently did this working ~50% time for 2 weeks in Hawaii. The plan was to take a vacation ... then something came up. However, I loved it. The vacation was chill (my goal was just to scuba dive or hike every day -- I didn't have a packed itinerary), and since my colleagues knew I was trying to be on vacation, I was able to focus on the one urgent project and avoid all other meetings. I wound up being both productive and relaxed, getting 2 awesome weeks for the price of 1 week of vacation days =) I don't know if I'll ever be able to get away with something like that again, but I sure hope so.
I've also tried to do this while visiting friends/family, and that didn't always work quite as well. In one instance, the friend's internet wasn't good enough to use for Zoom (!!! even now, you can't assume!!), and in another, my family wasn't good about not distracting me while I was "at work".
posted by Metasyntactic at 1:12 AM on August 23, 2022
I've also tried to do this while visiting friends/family, and that didn't always work quite as well. In one instance, the friend's internet wasn't good enough to use for Zoom (!!! even now, you can't assume!!), and in another, my family wasn't good about not distracting me while I was "at work".
posted by Metasyntactic at 1:12 AM on August 23, 2022
I did something similar earlier this year for two weeks, working East Coast hours 6 hours ahead, (so ~3pm-12am local time = 9am-6pm Eastern time).
All in all it was totally worth it, but it was a bit harder than I anticipated, mainly because:
- I've always been a morning person, and I didn't realize how difficult it would be to start working in the mid-afternoon, which it turns out is the absolute nadir of my energy and made for a rough start every single day. (I realize this is how lots of people feel about mornings -- I've just been lucky enough that my personal circadian rhythm meshes with the arbitrarily valued rhythm by society.)
- I found it a bit difficult to go to bed immediately (like, I couldn't stop working at midnight and then be asleep at 12:15am) -- I definitely needed some wind-down time, which in practice meant that I went to bed after 1am every day.
- It was great to have mornings free to walk around or do cultural things, but I found that the negative anticipation of starting the workday in the mid-afternoon did kind of put a damper on things -- as in, I enjoyed being able to check things out on weekday mornings when they weren't crowded, but I also felt like I couldn't totally "let go" because I knew I was starting a full workday in the mid-afternoon.
- Every single weekday dinner I ended up ordering delivery, mostly because I couldn't peel myself away for an hour plus at local dinner time to accommodate cooking. This is probably more of a YMMV depending on your job though.
I don't want to come across too negative of course! The advantages and privilege of being able to do this were tremendous -- I just think it's worth remembering that when you're working, it's still work, and maybe to think a little bit critically about your own personal circadian and energy rhythm and how best you can accommodate that.
posted by andrewesque at 6:26 AM on August 23, 2022
All in all it was totally worth it, but it was a bit harder than I anticipated, mainly because:
- I've always been a morning person, and I didn't realize how difficult it would be to start working in the mid-afternoon, which it turns out is the absolute nadir of my energy and made for a rough start every single day. (I realize this is how lots of people feel about mornings -- I've just been lucky enough that my personal circadian rhythm meshes with the arbitrarily valued rhythm by society.)
- I found it a bit difficult to go to bed immediately (like, I couldn't stop working at midnight and then be asleep at 12:15am) -- I definitely needed some wind-down time, which in practice meant that I went to bed after 1am every day.
- It was great to have mornings free to walk around or do cultural things, but I found that the negative anticipation of starting the workday in the mid-afternoon did kind of put a damper on things -- as in, I enjoyed being able to check things out on weekday mornings when they weren't crowded, but I also felt like I couldn't totally "let go" because I knew I was starting a full workday in the mid-afternoon.
- Every single weekday dinner I ended up ordering delivery, mostly because I couldn't peel myself away for an hour plus at local dinner time to accommodate cooking. This is probably more of a YMMV depending on your job though.
I don't want to come across too negative of course! The advantages and privilege of being able to do this were tremendous -- I just think it's worth remembering that when you're working, it's still work, and maybe to think a little bit critically about your own personal circadian and energy rhythm and how best you can accommodate that.
posted by andrewesque at 6:26 AM on August 23, 2022
Greece, for example, seems like it would require to get a work visa to do this because Schengen visas do not allow for employment.
In theory you need one, in practice it is exceedingly unlikely the Greek state would notice you are doing this and bother to do something about it.
You should do your due diligence of course (and obviously YMMV in another country) but generally the system will blithely ignore you until you do something that attracts the attention of the tax service (e.g. wire a monthly paycheck in/out of the country, sign a long-term lease for a property etc).
posted by each day we work at 6:55 AM on August 23, 2022
In theory you need one, in practice it is exceedingly unlikely the Greek state would notice you are doing this and bother to do something about it.
You should do your due diligence of course (and obviously YMMV in another country) but generally the system will blithely ignore you until you do something that attracts the attention of the tax service (e.g. wire a monthly paycheck in/out of the country, sign a long-term lease for a property etc).
posted by each day we work at 6:55 AM on August 23, 2022
These make interesting reading, I’m coming at it from the other side as I have a house I rent and I’d say maybe 50% of our Airbnb clients are doing this, it was much
I agree about internet issues, that really is the biggest problem. Always have a SIM card backup. Or if possible see if there’s a co-working space anywhere nearby you can use. Remember to check for noise around your accommodation, eg a donkey or musicians or scooter rental … fun local colour on holiday, potential nightmare on a phone call, or if you need to sleep in because of working hours.
posted by tardigrade at 10:06 AM on August 23, 2022
I agree about internet issues, that really is the biggest problem. Always have a SIM card backup. Or if possible see if there’s a co-working space anywhere nearby you can use. Remember to check for noise around your accommodation, eg a donkey or musicians or scooter rental … fun local colour on holiday, potential nightmare on a phone call, or if you need to sleep in because of working hours.
posted by tardigrade at 10:06 AM on August 23, 2022
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