If you work anywhere near global mobility, tax or payroll, you have probably felt it already. The rules we have been relying on were not built for how people actually work today.
Remote work across borders is no longer a fringe scenario or a short term workaround. It is baked into how companies hire and how individuals choose to live and work. That is why the recent public consultation from the OECD on the global mobility of individuals is a genuinely positive step.
But reading through it, one thing becomes clear quite quickly. The guidance is moving in the right direction, but it is still catching up with reality.
There are a few areas where the gap between policy and practice is particularly obvious.
Independent Contractors & WFA: A Missed Opportunity
The OECD guidance paper was very helpful for short-term cross-border remote work scenarios for employees, but unfortunately did not go into depth on the topic of independent contractors.
This is partly because a lot of the current conversation still assumes a traditional employee and employer relationship. That is understandable, but it misses a huge part of what is actually happening on the ground.
Freelancers, consultants and independent professionals are working remotely across borders every day. Many of them are highly mobile, often spending short periods in different countries, and in many cases they have no local clients and no real reason to be physically present where they are staying.
Think about a self employed marketing consultant spending a few months in Costa Rica, working entirely for overseas clients. No local income, no local office, no local economic footprint. Yet the questions start immediately. Where is the income sourced. When does tax residency kick in. What reporting is expected.
These are not niche edge cases anymore. They are becoming more and more routine, especially with the fractionalisation of work. And the lack of clear, practical guidance for this category of workers when it comes to international remote work was an opportunity missed in the recent OECD guidance.
Digital nomad visas solved immigration first, not tax
Another missed opportunity was around digital nomad visas.
Over the last few years, many countries have introduced digital nomad or remote work visa regimes that explicitly allow people to live in one country while working for employers or clients elsewhere.
From an immigration perspective, these visas are often very clear. They are designed to remove ambiguity around right to stay and right to work. In some cases, they even try to provide a degree of comfort around tax exposure.
Where things fall apart is in how these visa regimes interact with domestic tax systems.
The structure of digital nomad visas varies widely from country to country. Some include explicit income thresholds, time limits, or restrictions on engaging with the local economy. Others are much lighter touch. The immigration rules may be clear, but the tax consequences are often left implicit or, worse, assumed.
That gap matters, because people make decisions based on the visa they are granted.
Malta is a useful example of what happens when immigration and tax frameworks are not properly aligned. When Malta introduced its Nomad Residence Permit, the messaging to remote workers was reassuring. The visa permitted remote work for overseas employers, and many individuals reasonably understood that their foreign income would not be subject to Maltese tax.
In practice, the tax position turned out to be far less clear, particularly once individuals spent longer periods in the country. As explored in this Fragomen analysis, uncertainty around how income tax exemptions were applied led to conflicting interpretations and genuine confusion for permit holders. Malta has since worked to address these issues, but the episode highlighted a broader problem.
When immigration policy signals tolerance or encouragement of remote work, but tax rules are not clearly aligned, certainty breaks down. Individuals lose trust in the framework, and employers struggle to give confident guidance.
This is not about creating blanket tax exemptions for digital nomads. It is about clarity. Where a visa explicitly permits remote work, there needs to be clearer guidance on how core tax principles are expected to apply, including residence, source of income, and reporting obligations.
Without that coordination, digital nomad visas risk solving only half the problem, while quietly creating another.
Immigration permission does not mean tax clarity
Another trend that keeps coming up is the growing number of countries that allow visitors to work remotely under standard visitor visas. It is a pragmatic move. Policing remote work is hard, and in many cases it does not harm local labour markets.
Take New Zealand. From January 2025, visitors can work remotely temporarily for overseas employers or clients without breaching visa conditions. From an immigration standpoint, that is refreshingly clear.
From a tax standpoint, it is anything but simple.
Tax residence thresholds still apply. Day counts still matter. Treaty positions still matter. Too often there is a risk of false comfort creeping in. People think they are compliant because immigration says yes, while tax and payroll exposure quietly builds in the background.
The bottom line is tax rules and right to work eligibility are two different subjects and need to be treated accordingly.
Payroll and social security are where problems actually show up
If you ask employers what keeps them up at night with remote work, it is rarely personal income tax. It is permanent establishment, payroll tax and social security.
While the OECD guidance did an excellent job allaying some fears around permanent establishment, it did not cover payroll tax and social security, which remain a patchwork of different local regulations that can be overly burdensome for companies trying to navigate.
These obligations can be triggered too easily and too quickly for comfort. They often apply even when permanent establishment tax does not. And they are usually the first thing regulators look at when something feels off.
The consultation only briefly touches on this. There is very little practical guidance on when payroll withholding kicks in for short or medium term remote work, how social security should be handled with or without treaties, or what employers are realistically expected to do when they have no local payroll setup.
This lack of clarity pushes companies into two camps. Either they become overly conservative and block flexibility, or they take risks they do not fully understand.
Neither outcome helps anyone, so we hope there is more progress on developing a more practical, co-ordinated approach to this.
Hire from anywhere is not the same as letting someone work abroad temporarily
One of the biggest shifts we are seeing is the move from work from anywhere as a perk to hire from anywhere as a strategy.
One is an employee perk.
Another is a business need.
Hire from anywhere does not refer to people temporarily working abroad. These are roles designed to be performed remotely from day one, often indefinitely, and often across multiple jurisdictions.
That changes everything. Source of income. Employer obligations. Employment law exposure. Long term corporate presence risk.
Trying to squeeze hire from anywhere models into frameworks designed for short term mobility just does not work. They need to be looked at on their own terms, with guidance that reflects how intentional and scalable these arrangements really are.
Where this leaves us
The OECD deserves immense credit for engaging with this topic. The consultation shows that policymakers know the old assumptions no longer hold. They are trying to adapt global tax guidance to the way work is evolving today.
But modern remote work is messy, varied and fast moving. Self employed professionals, digital nomad visas, visitor permissions, payroll triggers and hire from anywhere models are already part of everyday working life.
Clearer, more practical guidance in these areas would go a long way. Not just to reduce risk, but to build trust.
Trust that the rules reflect reality.
Trust that compliance is achievable.
Trust that flexibility does not automatically mean exposure.
The way people work has changed. Global tax guidance needs to continue to change with it.
John is Co-founder of Work From Anywhere, a platform to help companies execute a work from anywhere strategy. John is a Chartered Accountant who speaks 6 languages and was previously the senior finance leader of a €4 billion division of FTSE-listed CRH Plc. John and his family are passionate about travelling and his eldest daughter, Rosa, while only 5 years old has already travelled to 25 different countries.
