Are you thinking about packing up and workshifting from an overseas location? Do you long to have your office on the beach in the Caribbean or perhaps on a hillside in the Swiss Alps?
With a business in the Caribbean and having spent a good portion of the past fifteen years working internationally in places like Papua New Guinea, Samoa, and Tortola, I wholeheartedly support the pursuit of the international workshifting dream. However, if you have not lived internationally or worked from overseas before, I thought that I would provide you with some details that you might want to think about.
1. Are you ready for challenges that come with living in a foreign country?
Living some place is much different than just visiting for a week on a yearly vacation. This might sound like common sense, but during my time overseas I've seen many folks pack up all of their personal belongings and move 5000 miles away from home only to arrive at a destination and realize a week later that they can't stand living there. If you can afford to do so, a pre-move visit is always encouraged and could help you to avoid a potentially costly mistake.
2. Moving is stressful.
Relocating to another city within your own country is difficult enough. In fact, stress wise, moving typically ranks as one of the most difficult life changes an individual can make. When you decide to workshift internationally and move overseas you can multiply the stress factor on a scale of magnitudes. Part of the allure of living overseas can be the challenges that one might expect to face. However, you need to really consider if you are ready for the language difficulties, cultural barriers, and bureaucratic red tape that can that can be associated with an overseas move.
3. Are you ready to be away from family and friends (support network)?
Yes tools like SKYPE, Google Talk, and even Twitter make it easy to keep in touch on an almost daily basis. But, homesickness and being away from family and friends around holidays and special occasions, and during serious illness, can quickly tarnish beachside living or skiing every morning. Before packing your bags check to see if there is an existing expat or workshifting community to help act as your surrogate support network.
4. What are the immigration policies at your desired destination?
Many countries require you to show proof of an onward ticket before they will even allow you to enter. You need to find out:
- How long can you legally reside in the country you wish to workshift from? (Is it thirty days, three months or one year?)
- If you need to renew your immigration status is it as easy as crossing the border for twenty-four hours and coming back in again? Or, do you have to go back to your home of record?
- Are there any passport stamp fees associated with an extended stay?
5. Can you legally run a business or work online at your chosen destination?
Will you be required to get a work permit? Even if you are running an Internet based business, some countries do not want you working within their borders. Other countries will make you fully disclose the type of work you'll be doing or the business you will be running and may require you to get a special work visa.
6. What will your tax status be?
Although you might not be working for a local company, you should check with the country's treasury department to determine if you have to pay local taxes. Additionally, if you are a United States resident living outside of the states you will need to determine if you qualify for the Foreign Earned Income Exclusion.
7. Will you have access to medical coverage and medical care?
Nobody likes to think about a serious medical condition arising. If you're heading overseas and currently have insurance you will need to find out if the hospitals and clinics in your new country of choice accept your policy. In the event that they don't, try to find out if you can you get an international travel add-on from your existing insurer or purchase supplemental expat insurance.
Once you feel secure with your insurance situation, you might want to find out what medical care is care like at the destination you are heading to. Consider the following, do you have a particular medical condition that requires special treatment or medicine? Can you get the help you need at your new location? Additionally, discern if there are any serious health concerns such as malaria or typhoid and look into proper prophylaxis and immunizations.
8. How is the cost of living?
In your home city you might be so familiar with the prices for everyday goods that you don't necessarily pay attention to the standard living costs. For your new location you may wish to research what can you expect to pay for every day essentials like rent, bread and eggs, a car, gas, and beer. Moreover, you might be accustomed to very low prices for water and electric utilities. Other costs to consider would be the price for mailing and shipping items and accessibility (and cost) of goods such as laptop batteries cell phone cables, etc.
9. Can you legally purchase property?
This question is for the hardcore, expat workshifter, but if you are going to be in a country for any length of time it certainly is one worth considering for living or investment purposes.
Although, it is important to remember three things:
- Property ownership does not necessarily make you a resident.
- In some cases countries will restrict the purchase of property by foreigners.
- Always do your due diligence to check for clear title and hire local legal counsel.
10. Everything else!
If you made it passed all of the items above then you can actually begin to think about your in-country workshifting needs such as, power supply, office space, and Internet access.
Final thought, do your research and you'll make out just fine!
If you have additional tips for workshifting internationally, I'd love to hear your thoughts in the comments.


