A Remote World Would Be More Accessible If Only….

While attitudes towards remote work are rapidly changing, there remain legal and administrative obstacles that stand between remote work, digital nomadism, and their full potential

Daniel Rosehill
10 min readAug 9, 2021


Not all that’s remote is accessible. A sample remote job post from LinkedIn that disqualifies all non US-based applicants. Screenshot: LinkedIn Jobs.
Working from a café in Ramat Gan, Israel. Photo: Author.

I’ve written recently about the rise in remote work. Like many, it’s a trend that I’m particularly excited about. Particularly as — being based in Israel — I know that it can offer a lot more opportunity than what’s available in my local geography.

What we’re witnessing right now is also what I think of as the Great Normalization of working remotely. I think that the change in attitudes towards remote work — and remote workers — is every bit as significant as the opening up of opportunity itself.

The Great Normalization of Remote Work is also quickly bridging the gap between us long time crusties who’ve been working out of coffee shops for years — the freelancers / consultants / self-employed people of this universe — and our more respectable brethren working in office jobs that have gone remote and who haven’t yet become accustomed to spending an entire working week in their pajamas. They’ll get there. Eventually.

Nevertheless, this period of transition — while incredible — is very far from complete.

In fact, I think it would be more accurate to say that it’s still in its infancy.

While skepticism towards remote work, and remote workers, is being chipped away at by the day, there remain bureaucratic and administrative issues that remain between where we are today (the remote awakening) and where we’d like to be tomorrow (a world in which everybody who wants to really can work remotely).

These are some of those issues that spring immediately to mind.

A fully remote world would be far more attainable, and opportunity to participate in it distributed far more equitably, if only:

Restrictive Country-Based Hiring Policies Weren’t A Major Thing

Anybody who has decided to stick their neck out into the world of remote work and what opportunities are currently out there has undoubtedly come across the phrase “remote from US” (or: “remote from Britain”, “remote from Ireland,” etc).

There are various reasons why companies might assert the qualification that the remote candidate they’re seeking to hire needs to be based in the same country they’re doing business out of.

The most obvious reason is that the job is actually a hybrid opportunity.

Even if somewhat irregular on-site visits are required (let’s peg that at once every two weeks) this already makes it extremely difficult for anybody not physically based in the same country to pull off the gig.

With many countries asserting seven day quarantine requirements on all international travelers, this pretty much makes the job a non-goer for anybody other than those who really like the thought of spending protracted periods of time in forced isolation (or who really really like collecting air miles).

This is the situation that we have now. There’s a lot of remote opportunity being created. But the ability to participate in it is often restricted to those living in that country.

The other common reason for this kind of requirement is a more bureaucratic one.

While much confusion surrounds the matter — and it’s a subject I’m not really qualified to delve into — there’s a general sentiment among US-based employers that it’s impossible to hire foreign-based talent, even for short contract gigs (knowledgeable accountants, feel free to chime in with your thoughts).

The system — even when it does permit international pairings to happen — also tends to make it anything but seamless for international-based talent to actually spend their time with US-based organizations getting work done and not filling out a long series of forms.

I could probably cobble together a short novel from the amount of W8-BEN forms I’ve filled out over the years just to take on short projects with American companies.

Internally, A&P departments often seem to regard “international” employees with suspicion and payments can be delayed for the most trivial of reasons (the record for my longest-ever overdue invoice is currently held by a surprisingly major American tech firm). Ultimately, it’s easy for those not in the system — in this case of the IRS — to just read the tea leaves and determine that the US labor market is a closed shop for them.

While fallacies persist about the impossibility of hiring foreign talent (for American companies), they are borne out of the confusion created by a labyrinth system of regulation that at the very least does make it seem like it’s very very cumbersome to hire foreign workers. These, in turn, owe their origin to policies of protectionism.

There’s an unspoken tug-of-war going on right now between the desire to keep jobs at home and the much vaunted desire to make the world remote-friendly. It’s about time to admit that they’re not compatible ideologies.

A fully remote world in which true digital nomadism is not just possible via workarounds but actually readily achievable cannot coexist with this kind of restrictive policymaking.

We Had Tax Laws That Were Simple For The Geographically Fluid To Understand And Which Didn’t Require A CPA To Interpret

Another obvious difficulty that those plotting lives on the road are likely to encounter at some point (whether in the planning or execution phases) is as follows:

The world as we know it today doesn’t really expect individuals to bounce happily between jurisdictions and continents while toting a laptop and passport in their carry-on luggage — even if its eminently possible for many to do just this.

It regards them as aberrations to the system. Not the norm. Which is why today’s crop of digital nomad pioneers have become expert in working around rather than within “the system.”

If we take your average country’s tax code as a surrogate for the model of behavior that’s considered broadly normative, individuals are expected to remain happily wedded to their country of residence, whether they have a right to stay there by birth or by naturalization. Indefinitely.

The problem is as follows:

Many companies’ compliance departments currently hire workers — remote or otherwise — with the expectation that they will remain tax citizens of the same country in which their hiring entity is based. I’ve heard of people taking elaborate measures like submitting all work from VPNs and referencing the day’s weather in the system they’re supposed to be in to cheat this system.

If they spend more than a certain amount of days not resident in that jurisdiction — 183 is a common number used to reflect “most of the fiscal year” — then that begins to create problems. This headache is often HR’s to enforce on employees that are otherwise happily working from another country without any desire to return to the vaunted “office.”

This requirement can be enforced contractually with digital nomads or those who have taken advantage of the pandemic to move abroad having to either re-contract or work with the organization in a revised capacity, such as by moving from a salaried role to serving as a contractor. But naturally this also risks destroying good faith and increasing churn. Once employees have found a company that is happy to let them work in a location of their choosing, they’re unlikely to stick with one that wants to control the location of their office.

In an idealized and remote-friendly world, such things would not be concerns. Has anybody thought about the concept of per-diem tax contributions? Pay tax to a country on a daily rate for however long you remain in that jurisdiction?

Perhaps they have. I’m no expert on the matter even though I’m happy to muse about it on Medium.

But I do know that any time I’ve discussed the idea of working overseas seriously with my accountant, there have been more potential issues than you can shake a stick at.

It would be great if tax were something that could be crossed off the (long) list of potential issues that stand in the way of true digital nomadism. Doors would open. Remote work could get even bigger.

Healthcare Were Truly Universal And Medical Systems Were Truly Integrated

Those who follow this blog are probably sick of hearing this, but I was recently diagnosed with ADHD. To help me craft these delightful compositions — I jest — I take (daily) a wonderful medication known as Vyvanse (lisdexamfetamine). If you enjoy reading these posts, that chemical deserves a line in the credits.

Now here’s something you mightn’t know about ADHD.

If there were a title for the world’s most bureaucratic medical condition to have, I reckon ADHD would have to be somewhere on the leaderboard.

The reasons?

The mainstay of ADHD treatment — psychostimulant medications — are controlled substances in many jurisdictions. And until somewhat recently, science didn’t really fully grasp adult ADHD and how often the childhood condition persists into adulthood. Even among the medical community, skepticism remains in parts.

Humans have a natural proclivity to abuse any drug that can have very desirous effects. And thus to keep ADHD meds off the street / being misused by those without diagnoses, they have to be kept under lock and chain. By healthcare systems and pharmacies.

While I could legally get a 30 day supply of Vyvanse into (say) Ireland provided that I arrived with the right labels on my medication bottle (note: even the thought of doing this on a recent trip to the US and being mistaken for a drug mule gave me anxiety), continuing treatment after that supply ran out would be another matter entirely.

Because while Ireland’s healthcare service (the HSE) has recently begun pushing for improved diagnostic pathways for adult ADHD, ADHDers from that part of the world tell me that the diagnostic process is still — for the most part — a disaster.

They say that, in the US, money can buy you anything.

But if you rocked into CVS or Wallgreens without insurance and asked for a 30 day supply of a typical Vyvanse dosage, your bill would come to somewhere north of $500. Like most, I don’t have that kind of cash lying around.

Ireland won’t recognize my diagnosis. Nor will many countries.

To receive affordable treatment, I’d need to start the process from scratch: presenting to a doctor being referred onto a specialty (typically psychiatry; the wait depends upon availability), perhaps repeating a boat-load of paperwork. And only then potentially having to repeat the same tedious process of trialing medications that took me the best part of a year to complete first time round.

And as this little pill makes a big difference in my day to day productivity that’s …. a rather major impediment to the idea of jumping sticks to move back there for a period.

The Rental Market Were More Remote-Friendly

A digital nomad friend was recently extolling the virtues of life in the Canary Islands.

A bunch of childhood friends had even relocated there temporarily and formed a little remote working commune on the Spanish archipelago.

Truth be told, I was tempted to join in the fun. At least for a few months.

But when I ran through the litany of things that might make that dream a reality, my head began to spin a little.

Firstly — see the health section above. I haven’t lived in Ireland — or any EU member state — in more than 7 years. ADHD meds aside, would I still qualify for a European medical card? Could I get my monthly asthma inhaler so that I didn’t suffocate? (Healthier folk have graced this planet than I, as you may have figured).

Next, we had the large problem of accommodation. My (expensive) rental contract — like most — precludes subletting. Big black letters tell me that if I sublet my place I’ll be considered in violation of the contract. And from that point on, eviction becomes a credible concern.

Like many, I can’t afford to rent two places simultaneously.

As a budding video-maker, my list of worldly possessions isn’t small. And it’s growing. A minimalist I am unfortunately not, even if the philosophy appeals to me.

That whittled options quickly down to putting my entire life in storage — not a great option if you’re planning on returning from an expedition relatively shortly — or entrusting the apartment to friends as minders. The latter didn’t do much for the whole financial picture.

What are the solutions for this?

If owning accommodation is out of the reach for many in this generation — currently, I feel like it is for me — then the least we can do is figure out a system to make renting less restrictive.

Because I reckon that the prospect of never being able to own your own home would feel a lot less bothersome while sipping coconut cocktails under some palm dream in Barbados.

Could no-subletting clauses be banned?

Could we create systems to ensure that subletting is safe for renters — and not a possible fast-ticket to having your life ransacked by randoms found on the internet?

These, and all the above, remain open questions.

The concept of a fully remote-friendly world is energizing and exciting.

There’s an entire world of opportunity that could be created around it. One in which our skillsets function as our passports and we’re free to move around the world so long as we obey the laws of the countries in which we frequent and support their existence by contributing taxation.

Pragmatically speaking, however, the world we have at our fingertips today isn’t the same thing as the one that would make this dream readily achievable. In fact, it’s very far from it.

We have tax codes to comply with that and remote employers that will take issue with our employment status if we spend more than 180 days working from somewhere else.

Medical systems that won’t recognize diagnoses from other countries.

And bundles of electronic medical records (EMRs) that work fantastically well in one geography but which are virtually useless once you leave that country’s borders.

And for those of us who can only envision a future of renting, the headache of trying to figure out a way to spend more than a couple of weeks in another country without running the risk of subletting or falling afoul of a landlord who can dictate whatever clauses he or she sees fit in a contract.

A fully remote world could be something glorious. But we have a lot of leg-work to put in in order to make that dream a reality.



Daniel Rosehill

Daytime: writing for other people. Nighttime: writing for me. Or the other way round. Enjoys: Linux, tech, beer, random things. https://www.danielrosehill.com