Cross border work burned me so very hard a few years ago.
I live in Canada, but got a position with Amazon where I'd fly around the US (and occasionally other countries) to do upgrades and launches of Amazon warehouses. Paid in US dollars because I was working in the US. A lot of fun, working with some of the best co-workers I've ever had. Most Monday mornings, I'd get an Uber to YYZ Toronto and fly to some new city and be back by Friday night.
Where I got burned was the weeks I did not fly anywhere and worked from home doing prep work. I didn't sync correctly with payroll and HR that I was doing this work in Canada, which implies that the Canada Revenue agency was owed my taxes for those days, not the IRS. But the company paid my taxes to the IRS since I was a US worker. (To be clear, they had a system to avoid this problem but I didn't understand and didn't set it up right).
Come tax time, I owed the CRA $15,000, and the IRS owed me $15,000. But there was 3-month long gap between the date to pay and the date I'd get my refund. We managed, but yeah that wasn't fun at all.
How could you have such a lucrative career and somehow not have $15k liquid somewhere? You could even just take out a margin loan from your brokerage and not liquidate any securities.
In my experience, when the tax man comes calling, it’s always just after a big move, big purchase, far away death in the family, or some other life event where you have less savings than normal.
Their Handbook talks a lot about what legal entities (first-party, third-party, etc.) are in place in different countries, for employees in those countries.
It’s a very common question/misunderstanding coming up in /r/Germany (English subreddit about Germany), people thinking they can just move to Germany while working for a company in the US. Technically, not an issue. But you now need to be employed according to German law, including all the taxes and similar payments that includes for employees, but also for the employer.
Same in Austria, if I want to work here remotely for any foreign company, then that foreign company would have to have a legal entity opened in Austria and hire me according to Austrian laws and pay employer taxes in Austria, for it to be legal and by the book, which of course, unless they already have an office there or you're John Carmack, Linus Torvalds or Fabrice Bellard, no foreign company would go through all this hassle just to hire you remotely.
Everyone says this insane amount of legal red tape and gatekeeping is the government's way to prevent remote talent brain drain to places like the US and prevent local remote work turning to outsourcing which, if true, is complete BS reasoning as every company who wanted to outsource did that already, before remote work became popular.
I feels it's just German and Austria having a cultural and national obsession with red tape and regulations for the sake of preserving the status quo, and not for improving things for the ambitious workers who wish for better opportunities than the local market can provide.
ATM, the only way to legally work remotely is either as a freelancer or opening your own company and contracting which come with their own set of pros and cons.
I honestly don’t understand why you’re singling out germany and Austria. The same holds true for Italy, Sweden, Canada, the UK, … - you cannot employ anyone without registering as an employer and following local labor laws. You sometimes can skirt it by setting up a contractor relationship, with all attached baggage. But there are companies that offer remote employment as a service- they have a local entity that serves as employer of record for you and take a fixed fee for that.
>I honestly don’t understand why you’re singling out germany and Austria
Because in those two countries, freelancing is the only way to skirt around the fact that no company will set up shop locally just for you, and if you freelance, you pay higher taxes than being a FTE, while also loosing almost all benefits that come with being a FTE like sick leave, paid vacation, and pension contributions VS for example in Denmark, if you're a freelancer, you also get pension.
Yes, in most other countries you have to freelance for remote work, but at least in other countries (Portugal, Romani, Bulgaria, Spain, etc.) , if you freelance and say goodbye to social and workers' benefits, you at least pay less taxes since you get no safety net from the government, not pay more taxes like in Austria and Germany while getting no safety net and no benefits.
Freelancers in Germany don’t pay higher taxes. They pay income tax like every employee. They loose the employers share of social security and pension, but the remedy for that is to adjust rates - you also loose paid holidays, sick leave and all of the other employment benefits, but same - reflect that in your rates. You can opt into pension if you choose to, some freelancers are even required to (see 1). If you don’t opt into pension, you don’t need to pay into the pension fund. Unemployment insurance is similar: you can opt into it when you start freelancing, but if you don’t, you don’t need to pay for it.
(Source: I am for social security and tax purposes a freelancer)
In Poland you pay 12.5% flat revenue tax as a contractor vs 17/%32% income tax as an employee, it's a no-brainer especially since you need to pay for health insurance anyway and you are never going to see the money taken from FTEs by the government for retirement. Unlike in Germany there is also no enforcement of false employment.
There is another way. Some companies offer this as a service. They have offices everywhere around Europe. A first-party can hire you through one of these services, and you would have all the benefits of the destination country.
Pretty sure you can add the US to this list. Try being a resident (or even a non-resident citizen! The US is pretty unique in that regard) working for a non-US company without declaring the income for tax purposes and see how it goes...
It is actually possible for a U.S. company to employ you directly as an employee (according to ASVG) in Austria without forming a legal entity. They of course have to pay Employer contribution to social insurance and other things (DB zum Familienlastenausgleichsfond etc.), and you as employee have to also pay the employee contribution to social insurance and income taxes. You probably want to hire a tax accountant to handle your monthly payslips etc.
(Disclaimer: This is not legal advice, I’m not a tax accountant/lawyer.)
I beg to differ. Currently living in Austria and working remotely for a UK company, they set up the contract through an Employer of Record service so it's all legit and above board. I didn't think it was possible either, then one day I decided to tell every recruiter who cold-called that I was happy in Vienna and not planning to leave; it turned out that a fair proportion of their clients were actually willing to consider this kind of arrangement and jump through the necessary hoops.
This is usually worked around by intermediary companies that hire you and then send you as contractors to the original company - taking a cut in the process.
> ATM, the only way to legally work remotely is either as a freelancer or opening your own company and contracting which come with their own set of pros and cons.
For immigrants from most countries, this only works if they are really wealthy or very lucky. We basically just let people buy themselves into immigration via Cyprus nationality, but hard work or education are minor points in a kafkaesque process to get in.
In the US it's the same: if your company is in California and you hire a remote employee in Utah you need to register your company as a "foreign corporation" in Utah, do Utah payroll and follow Utah labor laws.
Actually it's more exciting because not only can you get in trouble for violating the Utah labor laws, as a California company the employee can complain if they are not treated in accordance with certain California rules (that bind to the company rather than the employee) -- and win.
In practice though this is all pretty easy to mange; all the rules above devolve down to simply: 1 - file a couple of forms and 2 - tell your payroll company. Health insurance isn't uniform across the country so in practice it's the most complicated part to deal with.
The same in The Netherlands. However from what I understand in the EU it’s a lot easier. For example between France and The Netherlands the company doesn’t need a full office. You just need to register with the countries tax office and pay taxes.
In a lot of cases the taxes are mostly the same just paid to the employees country instead of the companies one.
It’s mostly knowns in administration what companies seems scared of
AFAIK this is a solved problem. There are plenty of global PEO that take care of the local laws to hire people in different countries. I currently use Globalization Partners, know about a YC one called via.work and have worked with other called AIMS.
I think, there are many people who work remote in their home country and then travel across the world, and in many countries that can be illegal if you stay too long.
I accidentally did that once. Moved somewhere for half a year on a tourist visa, kept working remote for my employer in Germany. I simply did not realize there was a legal issue there.
The vast majority of tourist visas don’t allow you to work at all, so it’s not only "stay too long"
Note that even within the USA, complications arise when you live in one state and work in another.
Some (many?) states have mutual arrangements where you can take a tax deduction for income taxes paid to another state, but I don't think they all do. You might end up paying double taxes! And even if the two states do have an arrangement, your employer might not set up tax withholding correctly between the two states, so you have to carefully check your W-2s to make sure you didn't overpay (or underpay, leaving you with a big bill in tax season) throughout the year.
Also, health coverage tends to be very state-specific, so you might get stuck with less-than-ideal coverage for your local health providers if you're on a health plan intended for another state.
Figuring out who to pay the tax to could get complicated, but you will never legally owe double taxes for the same income to different states. Whatever agreements or laws these states have do not change this.
If state B had such a law then it would be illegal. Even California, which is notorious for its tax policies, draws the line at “California-sourced income”, unless it was from a tax-free or lower taxed state, in which case you will only owe the difference.
I’m not aware of any state where you would pay taxes without being a resident. Afaik it’s only complicated when you’re residence changes often or you technically qualify as a resident of multiple states because of travel.
edit:
I should have stated, assuming you are not physically working in that state.
There are several states that tax your income based on the location of your employer even if you do not live or work in that state. New York being the most prominent example since they actually changed their policy during Covid. (Presumably to capture the lost tax revenue from people living in New Jersey who stopped commuting into NYC and started working from home instead.)
> But a handful of states take a different, more aggressive approach. They use special rules to tax remote workers based on the location of their employer’s office — even if the employee doesn’t physically work at that location, according to the Tax Foundation.
> Six states took this approach before Covid-19 upended office work: Arkansas, Connecticut, Delaware, Nebraska, New York and Pennsylvania. But now, that policy is facing fresh scrutiny since many people weren’t telecommuting by choice during the pandemic but were forced to work from home because their offices had closed.
> The State of New York has so far said that it will continue the policy despite the pandemic. If you don’t live in New York, but your “primary office” is there, “your days telecommuting during the pandemic are considered worked in the state” unless your employer has a formal office at your remote work location, the state revenue department says on its website.
Did you read the rest? There’s nothing that says this is the case for people who never worked in NY, but work for a company located there.
> It means that if you usually worked in New York but are working remotely from your home in New Jersey during the pandemic, you’ll still owe New York state income taxes, said Alan Sobel, president of the New Jersey Society of Certified Public Accountants.
Almost every state considers any income for work done while you are physically within the state as income sourced from the state. This means you pay taxes whether you are a resident or not. Most states have some sort of threshold, either number of days or earned income. For tech workers you are likely to hit earned income thresholds pretty much instantly as it is usually prorated according to the number of days you are in the state. That said, a huge number of people just commit tax fraud by never paying or filing. Mostly only CA and NY spend any significant resources identifying and pursuing these people.
Concur/SAP now has an E&Y service that tracks how many days you worked in a state through your expense reports. (So obviously doesn't catch personal travel where you were working.) I was actually expecting to get hit for a couple short trips last year. I wasn't so there must have been some sort of threshold even though NC supposedly kicked in with even a single day.
But, yes, in general people pay even less attention to this than they do to paying use taxes and my accountant has never asked me anything about this kind of thing in the big questionnaire he sends me every year.
Was it looking out for you or for your employer? There are two things to consider - whether or not your employer needs to withhold versus whether or not you need to file. Lots of states are much more lenient to employers but still very strict to the employee. It is pretty common for a worker to need to file while the employer does not need to withhold or face nexus.
Wages and salaries. Wages and salaries for services performed in California, regardless of the location of the employer or the employee (or where the payment was issued), are taxable to nonresidents.
Of course, people widely don't follow these rules and many states have minimum cut-offs of various sorts but a lot of states are starting to crack down.
The FTB publication linked in that article states:
“Wages and Salaries
Wages and salaries have a source where the services are performed. Neither the location of the employer, where the payment is issued, nor your location when you receive payment affect the source of this income. Part-year residents include on Schedule CA (540NR), column E or Short Form 540NR, line 32 all wages and salaries earned while a resident, regardless of where the services were performed. Nonresidents include the income for services performed in California.”
Without more clarification that would seem to suggest remote work would not be taxable since the services are not performed in CA.
If I'm working on a computer in a state, and the location of the employer is irrelevant, it would be hard for me to argue that I'm not performing services in that state--even if my full-time residence is elsewhere. Where else would I be performing them? But IANAL.
Where you are. You are not working on a computer in state, you are working on a computer on your desk that is talking to a computer in that state. Not much different from phones really, do support people technically work in multiple states because they use devices (phones) in those states remotely?
I think we're agreeing. What matters is where your body is--not where a computer you're connecting to is located or where your employer's HQ or other office is. Or where the person you're providing support to lives.
NY defines a resident as someone that has spent at least 30 days in the state (particularly someone that has been living in the state before).
So residence in the literal word sense is moot. If you travel there enough, regardless of where your official house is located....for tax purposes , NY bureaucrats will consider you a resident of NYS.
Yeah, I know a number of people in NH who were working more and more remotely for a company with a MA location even prior to the pandemic, who switched their status to be officially fully remote. Live in MA/work in NH (no income tax) or live in NH/work in MA? Doesn't matter; you pay full income tax to MA.
Yes, but if you are working remotely from a state (or attending an event, meeting customers, etc.), you are performing work in that state. You're not if you're just on vacation.
Historically, most people and most states didn't really pay attention to routine business travel but that's starting to change.
California has a very broad definition of what being a "resident" is, so you can be a full-time resident of multiple states despite only having a single domicile and mailing address.
States generally either tax the global income of their residents (e.g. California), or they tax income earned within the state (e.g. Connecticut). If you are a resident of the former but earn your income in the latter, then you would be on the hook for double tax unless there is a specific exception.
> California has a very broad definition of what being a "resident" is, so you can be a full-time resident of multiple states despite only having a single domicile and mailing address.
No, it doesn't.
> so you can be a full-time resident of multiple states despite only having a single domicile and mailing address.
You cannot (well, not for California, though perhaps for some combination of other states), though you could be a tax resident of multiple states in the same tax year by having a series of domiciles during the year that each were not intended to be transitory when established.
(If you move directly from California to a foreign country, but retain citizenship and return to California for more than 45 days in a future tax year, you can also be a California tax resident with a domicile in a foreign country, but because it is keyed on being a California resident immediately before departing (and not just for any part of the tax year), that wouldn't be a backdoor way for multi-US-state tax residency unless the other state had a broader rule.
> States generally either tax the global income of their residents (e.g. California), or they tax income earned within the state (e.g. Connecticut).
California taxes global income of residents and income earned in the state by nonresidents; this is, AFAIK, the majority rule for states that have income taxes.
The tax implications in the US alone are fairly complicated. I expect they will get more complicated as stated wise up to companies based in one place but with workers in others.
A few years ago I was at an all remote company and there were several all staff emails along the lines of: “you absolutely need to talk to your manager before you move to another state.”
Certain states were not allowed.
I’m not positive but I think you owe state income tax in the state that you are physically in even if it is only for a couple of weeks or a month or so. Think of all of the tax fraud that has happened in the last two years.
> I’m not positive but I think you owe state income tax in the state that you are physically in even if it is only for a couple of weeks or a month or so. Think of all of the tax fraud that has happened in the last two years.
Just to clarify, the important "you" here is your employer. In many (if not all) states, having a full time employee work from a state establishes a tax nexus there, making the _employer_ liable for collecting sales taxes (if applicable) and requiring them to pay taxes on their business income to the state (again, if applicable).
It's the taxes on business income that can be quite painful for the employer. If the state has particularly high taxes, employing just a single person in that state may not be worth the additional cost in taxes.
This is all completely insane, of course. Doesn't the EU, made of actual separate countries, have a solution for this? So why can't the regions of _a single country_ do the same thing? Because we're a dysfunctional mess of a country, that's why!
I'm pretty sure the 'EU' solution for this is just that you are responsible for collecting VAT in every single country, regardless of any nexus. It's not actually really any simpler, but it does mean that taxation is no longer tied to a business presence. Specific tax laws still vary between countries.
I'm no expert on VAT, but it seems like this is a lot more like the sales tax case, where you are required to pass the cost on to customers. I'm sure companies prefer to avoid this, but it doesn't seem like it'd be nearly as strong a disincentive as having to pay business income tax in another state.
Oh, fair, I hadn't thought about it from that perspective. I think the challenge is that you still have to know the VAT nuance (and categories) for every country you operate in, and failure to do so correctly will result in you getting a tax bill, regardless. I don't think it's actually any less burdensome than the US' system, but I'm also not an expert on either system (just adjacent exposure working around it).
Sorta. If you’re a small company, you can just charge your home VAT. Registering for MOSS and paying out all VAT based on location of the sale would be something you do with your accountant when you get a little bigger.
>I’m not positive but I think you owe state income tax in the state that you are physically in even if it is only for a couple of weeks or a month or so.
The details vary by state. In some it's as short as one day but there may also be some minimum dollar cutoff--the laws are basically aimed at pro athletes and entertainers. I know I didn't have to file out of state taxes this year for some short business travel; all our expense reports are now audited for out of state working days.
Of course, you can usually get off with a certain amount of personal digital nomadism if you're not filing expense reports. But working for extended periods of time is getting into tax fraud territory. And you're absolutely right that a lot of people have been doing it, often without really thinking about it.
Including Canada. Well, at least non-covid Canada. I’m sure the team or the union has a healthy list of CPA’s and lawyers who specialize in this. More so in hockey, possibly soccer as well.
Oh, it's easy to track. And my accountant would have no trouble filing a bunch of additional state tax forms for me. But it would probably cost me a couple thousand dollars.
States should ditch the income tax altogether in favor of sales tax. Then you are paying where you are located no matter what. No "residency" concept (and all it's associated bureaucracy) is needed.
This doesn’t work. Taxes don’t just pay the governments bills, they also work to make sure the rich don’t get too rich (otherwise your land owners could get richer than the government and toss you out of power). We are literally watching this happen in the US where the rich are too rich and basically do what they want.
Also salary considerations based on sociological and geographic locations. This ideally should never come up, but do come up eventually, mostly from the HR side.
when it's about budgetary constraints, it's coming from the tax angle, but applied uniformly otherwise. When it's coming from HR, your imagination is the limit like a person's physical location, skin colour, sex, sexual orientation etc.
Exactly. This is quite common and is done all the time for remote workers, myself included.
The hiring company cannot treat you as a regular employee though (you are essentially a contractor), so you may have less 'rights' than a regular employee - i.e. your contract can likely be terminated a lot easier than a regular employment one. You may also not be able to get some benefits that a regular employee gets - ie contributions to pension funds, etc. These are often compensated by simply increasing your daily rate. I personally prefer it that way as I often find the benefits offered by the companies unnecessary.
There are also companies like deel.com that offer employers to hire people through their local branch office in pretty much every country in the world. FWIW I haven't used any myself but I have heard good things.
Hence I honestly consider remote working to be a solved problem already, but to each his own.
With respect of working rights, sometimes it goes the other way: I've worked for American companies from Mexico through a PEO (the ones in charge of hiring you). Given that these usually hire you as a full time employee, you are protected by the state rights. In Mexico that entails several things: Access to social healthcare, at least 25% of vacation bonus (additional pay for each vacation day you take), 3 months severance if the company fires you at will, compulsory contribution to the 401k equivalent, among others.
At some point us working in Mexico like this had better benefits than our peers in the US.
> At some point us working in Mexico like this had better benefits than our peers in the US.
I work for a small company who has set up a legal entity to employ me and others in the UK while being based in the US themselves. Our US employees outnumber our UK employees 20:1 and yet our UK employees have better benefits than the US employees, _and_ we cost less for an equal salary (basically US healthcare is so expensive that it ends up being roughly equivalent to employing people in countries where you don't have to pay 10% of someone's compensation on healthcare) even when you have to put up with all the legal headaches
There's nothing simple about setting up a company.
Hiring people as contractors rather than employees probably does simplify things. But a contractor may, for example, not be able to work for you full-time and you may not be able to offer them benefits beyond base salary. The bottom line is that, for a small company especially, hiring an individual who requires a lot of special care and feeding is probably more trouble than it's worth.
Why would a contractor require special care? On the contrary. They supply you the work, you pay for their services, like you would a software company. The benefits they choose for themselves and factor those in in the rate they ask you. There are differences of course, an employee may be more loyal, but that's a different discussion.
Because if you've been following gig work/contractor debates, there are constraints on who you can classify as a contractor in many places. And depending upon the circumstances, that person also loses out on things like RSUs--and hourly rate probably won't compensate. To be clear, companies do do this but it's not as simple as we'll pretend you're a contractor and you can send us an invoice each month.
In Germany that would be seen as fraudulent employment, because they work 100% of the time for one client. and it is de-facto employment. It depends on the country of course.
Each team member a self employee with their own company. We always tried to solve it that way. We paid everyone the full cost of taxes, healthcare etc. Full cost to the company for an employee in the HQ country, was the same for one outside, in the same economic region. We set up long term contracts.
We had maybe 30+% of the team working that way, if we got big enough in a country outside the EU we set up a subsidiary there. Often a real pain to administer with a team of 100 people:, but sometimes the only way to make it work. Indonesia, India, Kenya, Burkina Faso, Mali.
You'll likely have massive IR35 (UK legislation specifically) issues doing this unless you set the contracts etc up just right. But in theory yes this is probably the best approach.
You can also use an umbrella contracting company to run the business for you, and employ you with normal salaried employment structure, including pay your pension, healthcare or other salary packaging.
Of course the original hiring company benefits/RSUs etc can't be passed through easily, you need to get those as cash.
Again though, that's not being employed by the original company. The advantage of being employed is the access to those benefits that you lose out on by using a middleman.
Getting those benefits as cash defeats the point of them being those benefits in the first place.
From the other perspective, I’ve also wondered about what it would mean to have a union for international remote employees.
Unions for tech workers are rare but if you’re working for a company with people scattered all over the planet, it’s a massive increase in complexity. I’ve never done any serious organizing, and the companies I’ve worked for have been relatively benign. But after almost ten years in satellite offices or remote work from home, it feels like I’m taking on risks here if I ever get into a dispute.
According to one organizer I talked to, you need to form unions in each country with “recognized units” of a handful of people. At my current company there are knots of employees here and there but we are starting to look like the General Assembly of the UN with one person per country. Then there’s all the varying rules on when the employer has the recognize a union.
Good questions. I unfortunately can't help with any insight.
But my personal policy is to only take jobs that I could walk away from and quit the moment anything I'd want union support for comes up. A union for international employees seems next to impossible, especially with the employer of record thing getting in the way.
Luckily the market for my skills is such that I can afford that policy. You should probably only consider international employment relationships if you are going to be paid a butt load of money and can find a replacement job very easily.
I’ve also thought of this. IMHO, it would be like a professional union, not one tied to a specific employer (so opt-in only). The job of the union would be to provide legal assistance to the employee and consult with employers who hire remote workers.
I have lots of thoughts for this, and it’s something I think about quite a bit as a remote worker. If this is something you are serious about, or just want to chat about, look me up.
I think one of the biggest questions we are facing is how do geography-based governments make rules for interactions that transcend geographical boundaries?
Whose laws apply when people from multiple jurisdictions interact with each other in a digital space? Which law takes precedence? I think we see this with property rights, privacy rights, workers' rights, business law, tax law, and so much more.
I think web3 may partially be driven by a desire to have a shared global system of currency, business registration, property registration, and more. For example, registering a DAO is global whereas registering a company, in the US, is at a state level.
I feel both afraid and excited at how we will start to more collectively govern global spaces.
N American example: Canadian living/working in the US, pay the US and state. American living/working in Canada, pay Canada/province and US. Trying to work from country A and live in country B adds complexity - larger companies probably have a tax nexus, but smaller ones might only deal with contractors so they can offload the costs/hassle.
And unless you win the lottery, USians in Canada don’t have to pay the US, really. Just file and summarize your worldwide investments.
I see lots of potential for a legaltech startup that offers an easy way for companies and their employees to not have to deal with this and to compute tax implications beforehand.
What I've heard from people who have had to deal with this sort of thing is that you can outsource it to some degree but there can still be a fair bit of legal effort and cost. Especially for smaller companies, it's often just not worth the effort.
I think this is the reason umbrella companies exist. You invoice them and they make the appropriate deductions for tax and social security contributions.
> I owed the CRA $15,000, and the IRS owed me $15,000
I’ll just add that there are extensive trade treaties between the U.S. and Canada that prevent workers from being double taxed on income, which is why in this particular case it nets out. This might not have been the outcome if this was the U.S. and another country.
Honestly? 1500 words before this post even gets anywhere.
>In only a few months, the coronavirus (‘COVID’) pandemic had devastating economic, social, and health impacts worldwide. Today, millions of lives have been lost, and the end of the crisis seems it may finally be in sight
Here's 37 words that literally no one needed to read.
I've found the same over the past 4 years. Escaping the overburden of 'first world' countries can be extremely liberating and help get shit done.
Now that I'm hiring staff this stuff actually applies but whenever there is information presented it's "speak to a legal representative" as the bottom line. When you speak to someone pro bono it's "depends on what country you're in, been in, born in, planning to stay in", then when you finally pay it's still your responsibility if something gets messed up.
There's companies out there that claim to solve these problems for you, I fired one of them this week because they couldn't get the basics of pay the people on time right.
>The pandemic has also accelerated an already existent movement of remote working.
The very next line that will allow for that.
This info also doesn't have a long lifespan as laws are always changing and digital nomad visas are becoming more common. In 2 years time much of the information may not even apply to the country that you're living in.
I live in Canada, but got a position with Amazon where I'd fly around the US (and occasionally other countries) to do upgrades and launches of Amazon warehouses. Paid in US dollars because I was working in the US. A lot of fun, working with some of the best co-workers I've ever had. Most Monday mornings, I'd get an Uber to YYZ Toronto and fly to some new city and be back by Friday night.
Where I got burned was the weeks I did not fly anywhere and worked from home doing prep work. I didn't sync correctly with payroll and HR that I was doing this work in Canada, which implies that the Canada Revenue agency was owed my taxes for those days, not the IRS. But the company paid my taxes to the IRS since I was a US worker. (To be clear, they had a system to avoid this problem but I didn't understand and didn't set it up right).
Come tax time, I owed the CRA $15,000, and the IRS owed me $15,000. But there was 3-month long gap between the date to pay and the date I'd get my refund. We managed, but yeah that wasn't fun at all.