Question working abroad

[CaptainCrunch]

So I've been pondering this for a bit, and especially with the cold weather


I work for a company where most employees are virtual, we all work from home with clients in the US for example.


What would I have to do if I wanted to move to the States or anywhere else while I'm working a job where all I need is a internet hookup and my laptop?


I would merely be changing my address. I have no office to go to.

[nfotiu]

If you are going to keep it all above board, you'd need some kind of visa. I'd guess that if your company was willing, the TN visa could be an option depending on the type of work.

[bizaro86]

If you are truly location independent, I think I would consider starting with a 6-8 week vacation wherever you are considering. Get a furnished rental and try it out.

Keeps the visa problem for later, plus you can explore neighborhoods, etc for a more permanent place. Plus, if you leave right now you'll miss the rest of winter.

*my phone corrected winter to winterrorism. Seems appropriate..

[CaptainCrunch]

I like that idea a lot, pretty smart Bizaro

[calgarygeologist]

If you wanted to seriously consider this I would think that Mexico, Central America or the Caribbean would be better options than the US. I think it would be easier from a Visa perspective and probably cheaper for taxes.

Infrastructure might not be as reliable though.

[CaptainCrunch]

I don't know if I would be interested in Mexico. But working my last 15 or 16 years in the Caribbean would be really cool.

[Cheese]

There are a ton of guys and gals doing that in Asia. Philippines, Thailand, Vietnam, Korea.
Very cheap to live there, great weather year round. The only issue is working the opposite side of the clock which isn't much of a negative.

[Hockey Fan #751]

Originally Posted by calgarygeologist

If you wanted to seriously consider this I would think that Mexico, Central America or the Caribbean would be better options than the US. I think it would be easier from a Visa perspective and probably cheaper for taxes.

Infrastructure might not be as reliable though.

I would think that he'd have to continue paying taxes in Canada, no? If the company he works for is Canadian.

You can stay in the US as long as 6 months with a tourist visa so as long as you come back to Canada before it expires each time, you're probably fine.

[wwkayaker]

Originally Posted by Hockey Fan #751

I would think that he'd have to continue paying taxes in Canada, no? If the company he works for is Canadian.

You can stay in the US as long as 6 months with a tourist visa so as long as you come back to Canada before it expires each time, you're probably fine.

You can’t be in the US for 6 months, leave and then return for another 6 month stint. The IRS has a formula to determine how many days per year you are there and if you exceed, I think 183 days on your 3 year average, you may be required to pay taxes in the US.

[Strange Brew]

There are a lot of great things about living in the US IMO, but if you can truly work from a home office anywhere in the world, there are some exciting options out there with favorable visa and tax considerations.

I love the Caribbean but I would be wary of island fever if I actually lived on one of the islands.

The working vacation idea is a great idea. Hell, you could take 2 or 3 of those every year and be a citizen of the world.

[metallicat]

Are you single? Kids? I'd consider a place like San Diego, but the health Insurance issue kind of sucks, unless work would pay for it.

[CaptainCrunch]

Single . . . no kids that I know about.

[nfotiu]

There are tax questions here and visa issues. You probably also want to consider health insurance issues. And then there's the questions about how ok are you about breaking the various laws that you'll most likely get away with.

If you are going to the US to work at all, even for a day or a few weeks, you need a visa of some kind. So if that's your plan, definitely don't tell the border agents. If you are doing multiple multi-week stints, I think you'll definitely get flagged. I'm sure you could likely get away with going to Arizona for 6 weeks every year saying it's your vacation, and working the whole time. Keep in mind though that you are not following the law.

You'll file your taxes in whichever country you've established residency. It's probably not a big deal either way depending on what the state taxes of whichever state you ended up in. Florida/Texas no problem... California, you'll be paying more. The tax will make sure you are just paying the higher of the state/Federal vs provincial/Federal, so no double taxes.

If you are going on visitor rules, and pretending you aren't working, I think you can spend a maximum of half the year minus a day, either continuous or in different trips.

The various health care plans all have different rules you'd have to look into.

[Regulator75]

"I've worked a broad or two in my day..."

[Temporary_User]

Start googling "Digital Nomad." I've been on the road for the last year and a half. Currently living in Vietnam.

Technically you will need a business visa or working visa, but most just live with the tourist and don't get caught.

Most rent out an Airbnb for a few months and then move on when their visa expires.

Look into coworking spaces if you want to get some sort of office environment while on the road.

[_Q_]

You need a visa to work in the US, full stop. Even if the office is in Canada technically. How do I know? My wife's boss tried to get her to work down in the states while I was there the last three years. It's not as easy as it sounds and the costs for him were prohibitive.

Now if your company has an existing US office, you might be able to qualify for a TN visa, but you can't get a TN visa to work for a Canadian based company in the US.

On top of that, taxes and health insurance can be insanely cost prohibitive there.

If you could work anywhere, I would take the advice of some of the posts above and look elsewhere with more favorable tax and visa regulations.

[Strange Brew]

^ As for cost of living in the US, a lot depends on if your employer has a US health care plan. As previous poster points out, you’d need to transfer to a US based office which maybe is a deal killer right there.

But your US taxes won’t be insanely high. Especially if you move to a state with no income tax, and you’re not paying property taxes. Then they will be insanely low.

If you do “visit” the States for a longer term, make sure you understand what health coverage you have and if you want to buy travel health insurance. True for any extended trip I guess, no matter where you go.

You also have to factor in that you’ll be paid in CAD and spending USD.

[CaptainCrunch]

This is great feedback, a couple of things that I will factor in as well. I've only been with the company for three months, I think I would want to ensure stability.


I have two elderly parents, I live close to them to make sure that I can check in on them, and keep them socially engaged, I doubt I would want to start travelling for a while yet.


But I am going to check in with the company, because we do have American health care benefits, and they would be willing to pay me in US dollars I have an opening to negotiate something probably after I establish myself. I wouldn't move to the States without healthcare.

[Strange Brew]

I understand the elderly parent issue. After my Mom passed away, I am flying back and forth a lot to Calgary to be with my Dad, help with taxes, administrative stuff etc. Luckily you can do a lot of stuff remotely now, and we facetime a lot, but I know it means a lot for him to have personal visits.

And troubleshooting his computer problems from 2,000 miles away is tricky

[Muta]

I'm thinking about making a move south of the border too... likely San Diego if I can make it happen. Easiest way is to be 'digital nomad' or get a job offer from a company, correct?