Ask HN: Anyone ever do remote work from another country?

As far as working remotely: SSH sucks to use over the Atlantic. It's very very slow and the delay makes it no fun. Not sure if that was part of what you wanted to know. I can't give you much idea about taxes since it's the other way around for me.

Anyone ever take a US job and work remotely from another country?

I have been working as a freelancer / contractor from the Philippines. Most of my work comes from N. America but I also get work from Australia and Europe. The difference between self employment and a job is the tax forms involved. I have been offered a lot of full time positions, but all of them have been as a contractor. In other words, I give them a W-9, they pay me for my time and I worry about my own taxes.

How this works out depends on how well you jive with the client. Most clients won't work out, so you should be saying "no" a lot. The good clients make freelancing (almost) easy and enjoyable. Bad clients turn freelancing into a stressful grind. A bad relationship can be devastating for both sides and run your business into the ground. It takes time, practice and a lot of networking to create relationships with good clients and prevent relationships with bad clients.

Dealing with different time zones may be an issue. Every client has different preferences. Some prefer that you are available during U.S. business hours and others don't have a preference as long as you get the job done. I try to give myself some overlap in availability for at least a couple of U.S. business hours.

Your visa will likely be the most important issue. Many "nomadic developers" work on a tourist visa. You could argue the rights and wrongs on doing this, but you are unlikely to attract attention. However, you will have to do visa runs while on a tourist visa, and depending on your situation, this may play a big role in your decision. In other words, once the PITA factor of dealing with a tourist visa reaches a certain level, then you will likely be looking for another place to live.

Otherwise it's not much different than doing the same thing from within the U.S. If you have never worked remotely or done freelance, then the country you are working from will be the least of your logistical problems (assuming you aren't living in a third world country with terrible infrastructure.)

I have worked remotely for companies in other countries for extended periods of time quite a bit. I'm Australian but have worked remotely for companies in Canada from Australia for over a year, I have worked for companies in the UK while living in Canada and Australia for over 18 months. I have also worked for Australian companies from Nepal. In addition to this I have spent time travelling around various parts of Europe and Asia while working remotely for companies in Australia and the UK.

It's definitely doable and provides great freedom in your lifestyle. The different timezones can get a bit annoying though, the time difference between the UK and Australia is 11 hours so I would often find myself on Skype calls until 5am local time.

Using good collaboration tools like google docs and hangouts/skype really make this all go a bit easier. In some places around Asia(particularly Nepal, Burma etc.) internet can be a bit sketchy so it can be difficult to get fast turnaround times on communication/bug fixes etc.