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It's kind of the same in Canada even if we have mandatory vacations. At some point could WFH and had about a month of vacation every year. I love bike touring and travelling in general, and one year I took about 10 weeks of vacation in total. My boss started to suggest that I could also bring my computer to other countries and work from there.
I must say it was tempting to continue earning money while being able to live in another country. I could have spent a few months in some places, instead of a week. But I wasn't a fan of having schedules while "on vacation". Also, more paperwork.
Much of the US doesn't even have mandatory paid sick leave, let alone vacation.
EDIT: Americans do effectively get 12 weeks of unpaid leave, but only if they or a family member gets a "serious" illness. That only applies to businesses with more than 50 employees though (along with a few other caveats).
"Getting" unpaid leave is a misnomer. The employee isn't getting anything and they employer isn't giving anything.
It's a right. It is the right to leave without the risk of the employment agreement being terminated over that specific leave.
The employer ought to be grateful if an employee wants to return after being required elsewhere for personal reasons for 12 weeks.
Lots of companies lump in PTO and sick time, so that's sort of bullshit too.
What? I have 6 weeks and my wife 10 weeks of payed leave in the Netherlands. Nobody will expect anything of you in this time. Around childbirth you have 6 weeks as a partner, 3 months as a mom. All payed. Afterwards moms have about 3 months of payed leave, too. Then on top each partner has 3 months of payed parental leave that you can freely distribute over the first 8 years, your employer has basically no say in that. And oh yes, we have affordable public healthcare.
Just saying, in case you were considering...
In Texas, I had employers that counted use of sick leave against your attendance metrics, and would fire you if you used it more than 3 times in a given year.
In Canada you can get up to 16 months maternity leave. But the vacation is not as generous. I'm sitting at 3 weeks a year.
What you're describing isn't working on holiday but being a digital nomad, what your boss suggested. Friends of mine do it too. Go somewhere for 3 months, work from there. Usually in the same timezone or close to it and a cheap country so renting an airbnb isn't too expensive. From The Netherlands there are many options. Friends of mine go to Portugal(-1), Brazil(-4), South Africa(+1), Turkey(+1), Egypt(+1), Montenegro(+0), or sailing on the Mediterranean.
ten weeks vacation is a pipe dream in the states.
By law the minimum is only two weeks though. My contract gave me four weeks of paid vacation after a few years of employment. The other six weeks were just out of my pocket. I wasn't paid and just took this time off. And that's when my employer started to suggest that I could, maybe, work from remote places.
My company allows working from any other country in europe for up to 3 months a year, countries outside of europe are fine too but you gotta do paperwork for those.
So a handful of colleagues travel to spain together each year and work from there for like a month. I haven't gone with them yet, but it does seem like a pretty fun time. Apparently they found one specific vacation rental home that has a very good internet connection, and splitting the rent between them makes it pretty affordable.
Honestly, working while traveling sounds like a dream. I guess it would only really work if it came with a solid reduction in hours though.
I've heard of people doing that but I can't understand how they can because my work would have an absolute fit if I took the laptop out of the country. I connect to the service through a VPN so I really can't see what their problem is and the country I live in and the company I work for and even in the same country already.
I don't understand your last point so this applies generally to employees working abroad:
Many companies use geofencing on their VPN to reduce brute force attacks. If a single employee works from country X they have to put that country on the allow list, increasing spam and attack surface.
There is also the major concern of security of the laptop itself. Police/border control might force you to unlock the laptop. You are basically adding nation state industrial espionage to the threat model. It could also just get stolen. Or you connect to insecure network infrastructure ...
All this is a concern in your home country as well but most companies are aware of the risks in their own country and want to avoid adding the (unknown) risks of a second country.
Besides that, there are tax implications at least for the States.
It depends a lot on what you do and how chill your employer is. This one was an IT outsourcing company and I was taking support calls from multiple other companies. Officially calls were routed to an office with a call centre, and that's what clients were shown, but most of us preferred to WFH. The clients obviously knew it's outsourcing but sometimes their employees didn't. Sometimes I had to make them think they were calling ABC Inc's tech department. So the only "rule" was not to openly talk about it. We could be in "another building" but still be working for their employer. Just don't say that the "other building" is your summer house. Being in IT with that outsourcing company have let me get away with a lot of things that normally wouldn't be allowed if I would have been an employee of their clients.