Are You Considering Becoming a Digital Nomad?

I​f you are considering location independence, here are a few things to consider in preparation for being a digital nomad.

October 31, 2022

By: Bobby Casey, Managing Director GWP

digital nomad I​f you’ve been following my blogs for a while, you know I often write and speak about the digital nomad lifestyle. I call myself an “expat with commitment issues”. But think about folks who have commitment issues to things for a second.

Commitment issues to a job?

Commitment issues to people?

Commitment issues to a location?

W​hat can often be behind those issues is sometimes boredom, but could also be the number of times you’ve been burned by those things. Whatever has you seriously considering the nomadic lifestyle, brought you to the point where you’re probably trying to level-set your expectations.

I enjoy it. I’ve been doing this for years and I’m living my best life. I’ve been an entrepreneur for decades. Traveling around the world and meeting a host of different people from all walks of life, has been incredible.

Despite my bias, and for as much as I encourage people to look offshore for solutions in asset protection and a freer life, I think people tend to get a skewed and possibly over romanticized understanding of what it is to be location independent.

Life in general is better when you deal in the reality of what is or isn’t possible. So I’m going to run through some stuff that might take some adjusting:


You hear a lot of people talk about work-life balance. And yes, you need that. But many people have the full breadth of the day to crank out the work they need to do. So with more flexibility comes more room to fall into extremes.

Working from home, for example, actually saw people putting in MORE hours of work than when they had the structure of going into the office during prescribed hours. It was more acceptable to walk out at 5:30 P.M. than to log off at the same time.

With less structure comes a different balancing act. Rather than work-life balance, it begins to look more like work-life integration. Yes, you log off. Yes, you have your own time. But you-time isn’t the same time every day. You-time can be a few hours or several days.

Remember, as a nomad, you don’t need to cram as much stuff into a short period as you would being a tourist on vacation. So in some respects, you have more time to relax and take in the experiences. Allow yourself that part.


T​he lifeline between you and the rest of the world and most importantly your streams of income. This is the digital part of the digital nomad, upon which the whole premise of this adventure relies. Sounds more precarious than it is.

Technology is spreading, expanding, cheapening, and growing with each passing day. This means, places that once were totally analogue, are adopting technology and the infrastructures that go with it.

O​f course, service varies vastly from country to country, and even city to city. As does security. So part of your checklist as you head to new destinations includes checking out connectivity and service beforehand.

Equally important is protecting your computer and data, since you’ll likely be using open services in cafes and temporary lodging arrangements. I highly suggest investing in a good VPN service.

Tech and Comms

Since we’re on the subject, remember to consider compatibility with outlets, and portability of your phone plan. The last thing you need is to blow out your laptop because you didn’t check what your computer needed and what was actually available.

Also on the list of things you don’t need, is unexpected international fees on your phone bill.

Health & Wellness

I​f you have any chronic medical conditions or require regular prescription medication, you might need to fill out some paperwork and make sure you can get something comparable in the new country you are in. What is legal in one country might not be in another, and that sort of misunderstanding is worth avoiding.

C​heck in advance what the regulations and availability are for what you need in advance. Be sure to keep a copy of those prescriptions with you for reference.

I​t would likewise be helpful to learn how to say your condition or any allergies and restrictions you might have in various languages in the event of an emergency… or even avoid one.

Likewise, many countries require you to have health insurance to qualify for their digital nomad visas.


S​peaking of what visas require, there are some which require a certain type of physical address to qualify for the tax benefits associated with the visa. Portugal for example has a status known as “Non-Habitual Resident” to qualify for that, you need a certain classification of residence.

Don’t just take the landlord’s word for it. They register their properties, but are not liable when they mislead you on how the registered it. Make sure you consult with someone who understands the nuance of the requirements for the different visas.

Nomads will mistakenly use an AirBnB type address thinking that will sufficiently check the box for their “domicile” and are shocked by the tax bill they receive.

Taxes & Banking

Last, but certainly not least is the financial structuring and expectations. Like many of these things, it’s about doing it right and keeping compliant. A lot of that comes in the preparatory work, and once you’re done, you’re done.

A​re there tax obligations as a digital nomad? Yes, but they aren’t the same as being in your home country, and they depend on the kinds of income streams you have.

C​an you live tax free abroad? Yes, but there is paperwork to file with certain boxes you need to check.

If you are a self-employed American, for example, you would still have to pay social security and medicare taxes amounting to 15.3%.

However, income that is a Salary , Wages , Bonuses , Commissions , or Professional fees, could qualify for an exemption known as the Foreign Earned Income Exclusion.

T​here are also Foreign Housing Exclusion that can bring down your tax liabilities. The Housing Exclusion is 14% of the Income Exclusion.

For 2022, the maximum FEIE was $112,000, making the maximum Foreign Housing Exclusion $15,680. For 2023, the maximum exclusion will increase to $120,000, and the Foreign Housing Exclusion will increase to $16,800.

There is also a Foreign Tax Credit, which is a deduction you can claim for taxes you pay abroad. If Portugal levels a 10% tax on your income, then you might be able to deduct that 10% from your US taxes.

A​s for banking, you really want to find a few banks that are compatible with your needs. If you own a small business, and you plan to be a digital nomad, you want a bank that accommodates the needs of both those things.

Whatever has you taking a closer look at location independence, the main thing is the preparation. Set yourself up for success wherever you can, as there are plenty of surprises to come with this new lifestyle. It’s a very rich and fulfilling experience, but getting the nuances of the laws and obligations as well as being prepared to break from your home routines is integral to a successful endeavor.

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