Where to Travel with Remote Job

I am leaving IB for a pretty nice corporate role that is remote and I plan on using it to travel. I never studied abroad so I am considering leaving NYC and hopping around random airbnbs for 1-2 months at a time. 


Would love any suggestions of what are places to go and see and if anyone has done this before / has any input. I am working traditional corporate 9-5 hours on the east coast so europe seems doable and don't mind waking up early (in fact I prefer it) so thinking Hawaii too.


Two considerations I am trying to wrap my head around are

1) Costs - I am keeping my analyst salary but obviously not going to be making big money with my bonus. Ideally i'd like to keep my costs in check and not spend a lot but figure being out of NYC will help. In terms of flights my dad is a pilot so those flights will be me on standby and are not going to be any consideration. Hoping that I can just live a normal life, cook, take the metro, etc. but costs tend to go up as you explore a city. Any guidance for management of daily expenses will be huge.

2) Friends - I've done a lot of solo travel before and made friends in hostels and such but am a bit nervous leaving behind a base friend group in NYC. Will say my best best friends are not my NYC friends so it's not too bad but I'd like to make friends abroad. Any tips for doing this / any countries where locals are particularly open to newcomers?

 

I'm all for surf and snowboard spots. So, SoCal and Colorado. NYC and Miami also.

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 
Most Helpful

Few things:

1) Just because you are “remote” doesn’t mean you can pack off to the EU or Asia. You can only work where your company is registered to do business and pays taxes to. For some companies it’s a city, for others a few states, and others the US only. Very few (if any) companies are registered in every single country in the world, so even if the business has an international presence your travel options are limited based on the company you are working for. Based on all of this check with your company first on which locations you are authorized to work.

2) You are not legally allowed to hold employment on a tourist visa. Certain regions such as the EU allow you to enter visa-free for 90 days but you are only allowed to travel and do business activities (such as international conferences). You are not allowed to work or hold a job on that visa.

3) In response to  2) and the shift to remote work certain countries are offering a digital nomad visa which is essentially an extended tourist visa that allows working.

https://www.investopedia.com/countries-offering-digital-nomad-visas-519…

that you will need to apply for formally which will give you the right to work and reside in a country for a specified period of time. 

4) I would strongly recommend sticking to #3 but if you feel the itch to work in a county not listed above that your company is registered for you can try to get them to sponsor you for a work visa. That’s quite a bit more complicated because depending on the country you might have to show foreign language proficiency / and or have to agree to work for your company for a specified period of time. You will also be limited on how long you can be away from the country or else you’d lose the visa (unlike #3 which has no residence restrictions only maximum limits)

5) If you have deep pockets you can go for citizenship by investment: 

https://www.goldenvisas.com/?utm_source=GoogleAdwords&utm_medium=PPC&ut…

which would give you of course the permanent right to work and live in a country. Note that if you do one for any EU country, you automatically gain the EU citizenship which means no restrictions on work and travel across the European Union. Portugal is the best one as the residency requirement is minimal. Unsurprisingly, the EU ones cost quite a bit more than the Caribbean ones.

Happy to answer any clarifying questions on this. 

Array
 

IncomingIBDreject

Few things:

1) Just because you are "remote" doesn't mean you can pack off to the EU or Asia. You can only work where your company is registered to do business and pays taxes to. For some companies it's a city, for others a few states, and others the US only. Very few (if any) companies are registered in every single country in the world, so even if the business has an international presence your travel options are limited based on the company you are working for. Based on all of this check with your company first on which locations you are authorized to work.

2) You are not legally allowed to hold employment on a tourist visa. Certain regions such as the EU allow you to enter visa-free for 90 days but you are only allowed to travel and do business activities (such as international conferences). You are not allowed to work or hold a job on that visa.

3) In response to  2) and the shift to remote work certain countries are offering a digital nomad visa which is essentially an extended tourist visa that allows working.

https://www.investopedia.com/countries-offering-digital-nomad-visas-519…

that you will need to apply for formally which will give you the right to work and reside in a country for a specified period of time. 

4) I would strongly recommend sticking to #3 but if you feel the itch to work in a county not listed above that your company is registered for you can try to get them to sponsor you for a work visa. That's quite a bit more complicated because depending on the country you might have to show foreign language proficiency / and or have to agree to work for your company for a specified period of time. You will also be limited on how long you can be away from the country or else you'd lose the visa (unlike #3 which has no residence restrictions only maximum limits)

5) If you have deep pockets you can go for citizenship by investment: 

https://www.goldenvisas.com/?utm_source=GoogleAdwords&utm_medium=PPC&ut…

which would give you of course the permanent right to work and live in a country. Note that if you do one for any EU country, you automatically gain the EU citizenship which means no restrictions on work and travel across the European Union. Portugal is the best one as the residency requirement is minimal. Unsurprisingly, the EU ones cost quite a bit more than the Caribbean ones.

Happy to answer any clarifying questions on this. 

There is no such thing as “EU citizenship”, everything else is valid

 

I’m telling him about the legal specifics of his question because based on his question, I had the idea he was unaware of these things.

I can see where you are going with the “keep your head down” line but that is just asking for trouble especially when you are dealing with international countries. Even in the US you’ll get fired and your employer will get a myriad of tax penalties and fees (they’ve caught workers who lied about state to employer). Abroad, jail time isn’t necessarily out of the question as several laws would be broken simultaneously at the same time. Outside of visa and tax laws, there are also information sharing / data privacy laws that have to be considered and can compound one’s problems if they work illegally from a country. 
 

Considering the seriousness of the laws at play here, I don’t find your advice to be helpful and quite frankly is dangerous for OP to listen to.

Array
 

Facts. Did this for a month (traveled to central Europe) and no one cared. HR/Payroll at your company would obviously like to know about all the tax shit, but unless you wanna snitch on yourself there's no point in discussing

 

For the benefit of anyone reading this thread, the above advice from IncomingIBDreject is very legitimate. Countries can be very strict about work permissions and people do get turned around when entering countries if they say the wrong thing to immigration officers. Even if you are going to attempt to circumvent laws, you should definitely educate yourself on what laws exist and the consequences of violating them. There is a big difference between bringing your laptop with you to Ibiza for a week vacation and literally working full time from an AirBNB in Barcelona for 1-2 months. You don’t want to find yourself barred from entering a country and lose not only your money but also your time. So if you’re going to embark on working remotely for more than a week, do your research!

The tax implications to your employer are also very real. 

There is a massive digital nomad community that is growing very rapidly. Many European countries are also trying to attract digital nomads and are working to develop working visas specifically aimed at relieving digital nomads of the typical tax burdens and lengthy application waits that current exist. Unfortunately most countries haven’t fully sorted out these visas yet so your choice of countries is limited. Something to keep an eye on if you are interested in this lifestyle.

On the personal tax front, it is a nightmare to sort out taxes if you’re domiciled in a foreign country as an American. Be prepared to cough up extra $$$ to have experts assist you with your USA / foreign filings if you have an even moderately complicated return. I highly recommend that whatever path you take, you try not trigger tax residency in a foreign country — keep it in the USA.

CompBanker’s Career Guidance Services: https://www.rossettiadvisors.com/
 

There are programs setup for people exactly like you. Some to look into:

Hacker Paradise: www.HackerParadise.org

Remote Year: https://www.remoteyear.com

Noma Collective: https://www.noma-collective.com

There are plenty of others. I’m doing my first trip with Hacker Paradise to Valencia starting next week. It seems most people are in their 30s and work in tech, but we also have a variety of other professions (psychiatrist, small business owners, etc.). I believe Remote Year tends to have a younger crowd that is more about partying than culture, but that is just an impression from my online research. Find a program that works for you and give it a try. If you like it, you can do more.

CompBanker’s Career Guidance Services: https://www.rossettiadvisors.com/
 
CompBanker

I'm doing my first trip with Hacker Paradise to Valencia starting next week. 

How long are you going to Valencia? I love that city - I lived there for 6 months. 

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 

Just a month. Last time I was there was a long weekend in 2014, so very excited to actually get to know the city. If I really love it I may spend more time there in future years, but we’ll see.

CompBanker’s Career Guidance Services: https://www.rossettiadvisors.com/
 

The part that mentioned that the company you work for needs to be registered in the country you decide to take a 1-2 month trip to, are you aware of a website/list of companies that are registered in most countries? I figure the big tech companies like Apple/Meta/Google would have their own slew of registrations across countries but curious if there is a consolidate resources you may know of that makes it easier for those looking for exit ops from their current occupation.

 

Make sure that your company is ok with you working abroad, there are tax implications. They’ll definitely notice it if you stay out of the country for months at the time.

 

It can be a bit more complicated than that. If you don’t use a VPN, any reasonable tech department can see that you’re connected from another country. If you use NordVPN or something similar, they know that you’re connected via VPN (but not necessarily from where). At that point they could request you turn off the VPN and you’d be pretty exposed. Similarly unless you have a culture of using blurred backgrounds or a filter, you may start to raise suspicions. I’ve heard stories of people also needing to constantly study up on the weather conditions at “home” so they don’t get tripped up when asked about the weather. You also need to be careful with the lighting if you’re in vastly different time zones. Lastly, you better hope you don’t have a job that requires any travel or face-to-face meetings — not sure how you would negotiate your way out of visiting a client if your boss demanded (or worse, your boss says they are flying into your city and want to grab lunch with you)!

So it requires a bit more planning and concealment than simply a background filter!

CompBanker’s Career Guidance Services: https://www.rossettiadvisors.com/
 

Second this. Most US companies that offer remote work have strict rules about employees working abroad because they can be hit with big tax bills and fines. Same goes for the employees themselves. Definitely check with someone who knows about international tax. The US is a massive country and you can easily just go and move to some popular vacation spots in the states e.g., ski resorts, beach towns etc. whatever floats your boat.

 

Very practical tip that could save you quite some money: a lot of apartments that are listed Airbnb have an occupancy rate of <70%, so you can relatively easily negotiate a 30%-40% discount on the monthly price that you'd pay if you were to "instant book". The guaranteed, predictable cash flow is very appealing to hosts and you can use that to your advantage.

Source: I own an apartment that I rent out on Airbnb. I've had several people reach out to me over message before booking to see if they can strike a deal for a long-term stay. I personally prefer long-term guests as I do not have to worry about checking in/out multiple guests over the same time period and deal with potential cancellations that come with multiple bookings.

 
Dr. Rahma Dikhinmahas

Just waiting for the multi-page response from one of the two legal eagles in the thread about how dangerous it is to negotiate off-platform for an Airbnb.

😂

I'm not suggesting going off-platform btw, there's a message function embedded in Airbnb that people use to message & see if we can reach an agreement. Hosts can make special offers to guests directly through the platform, which would include the discount.

 

Hey I'm also remote and I plan to leave NYC area this summer when my lease is up. Some ideas I've had - Palm Beach FL, Chicago, Philadelphia, Jersey shore. I will be doing 2-3 month stints in each and living in furnished housing. I am still working east coast hours and must be working in the US so that reduces the appeal of the west coast (I am not a morning person).

 

For costs, I'd recommend looking into places that are cheaper to live in like Southeast Asia or Eastern Europe. You could also try looking for a long-term rental so you can save on daily expenses and cook your own meals. As for making friends abroad, I hear Aussies are pretty friendly and always up for a good time. Plus, you could catch some waves while you're there

 

Good luck waking up at to start your day at 3am in Hawaii. Outside of that, just explore the continental US, there is a ton to see and do across the country. I've driven across the country 6 times and have been to 48 states, trust me, there is something for everyone in the US. The Appalachian and Rockies are two great mountain ranges that cover like 14 states, the deserts of Arizona/Utah/New Mexico are beautiful and have some of the most extraordinary geological formations (there's a reason there are so many NPs in that corner of the country), ID and MT has some of the greatest forests and beautiful mountain roads, the Badlands of the Dakotas are great, the Pacific coast is incredible from Big Sur to San Diego Bay, etc.

And that's not even talking about cultural/historical points of interest. Do you like live music? Go to Nashville and Memphis. Good BBQ? Kansas City has some of the best in the world (don't @ me). Great Art? Chicago is home to some of the best museums and architecture in the world. Like history? Boston and Charleston both boast some of the oldest communities in the country. People seem to like Miami for some reason. Interested in film? LA has more theaters and showings than any other city in the country. Like sports? Plenty of cities have teams from the 4 major leagues and plenty more have minor leagues as well. Definitely plenty to see if you go looking. 

 

Nah that is no problem. I am from the west coast and when I worked from my hometown I loved waking up at 4am to workout, 6am login, and worked til 10pm - 1am. Still got my 6 hours of sleep and preferred it to the 6am wakeup. 

Assuming I don't workout before I can still wakeup at 3am and just do my workout after given hours are ridicuolously better. But great options for within the US, I will look at those for sure. San Diego is soemthing I'd love to do as I love surfing.

 

Yeah that would be amazing. The onyl downside with those is the hours are fine (working 4pm-1am) but I'd miss out on evenings / sunsets/ etc. but I guess I can have those on the weekends. Maybe during a month with vacation / long weekends. I love these places though. How hard is it to meet other like-minded people in these places?

And these opportunities exist! This is the third remote corporate role I interviewed with actually. It's not fantastic pay, I am basically making my base with no bonus so my TC is almost halved from IB. That being said it's on par with a typical corp dev exit. I didn't go looking for remote jobs specifically to be honest with you, I went looking for this industry that I am particularly passionate about and I wanted to focus on it and I am more strategic than deal making. Things just clicked out that it's going to be remote. 

 

Can’t speak from experience but I’d imagine it wouldn’t be too difficult, especially in a major city since there are a lot of young people constantly visiting plus a decent amount of foreigners working digitally like you. A lot of educated young people in cities speak English as a second language so wouldn’t imagine it would be that difficult, and at the worst it’s a good opportunity for you to pick up a second language! Whenever I’ve visited these places the locals seemed pretty friendly so I think you’d be fine. If not, you have the flexibility of being able to move on so at the very least it’s worth a try.

 

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"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 

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