I won’t lie to you: becoming location independent is hard. And as a general rule, the older you are – the more responsibilities you’ve collected, the more embedded in your current groove you are – the more difficult it is.

But if you’re motivated enough, every obstacle can be overcome.

I asked about 50 people what they believed was holding them back. Here are the most common barriers that emerged, and some of the options I’m aware of for getting past them…

Your job

Do you enjoy your job? And would your employer be OK with you doing it remotely?

Sadly, very few people can answer “yes” to both of those questions. If that’s the case, then location independence is only going to work if you find another job or a different way of making money.

Many jobs just flat-out need you to be in a particular place – like if you’re a doctor, or mechanic. If your job doesn’t require you to be in one place but everyone is based in an office, you’ll need to hold a lot of sway for them to make an exception for you. I’ve heard of it happening, but it’s not common.

If you are extremely valuable to your employer but they won’t entertain the idea of you working remotely, one option is to quit and hope they hire you back as a consultant – which happens more than you might think.

If you enter that arrangement having already told them that you’ll be doing it remotely, your problem is solved. As a bonus, you might be able to base the consulting gig on just a few days per week so you have time to pursue your own projects without cutting the cord completely.

What if you’re self-employed or run a small business that serves clients? Again, if providing your service requires you to be in person (hairdresser, interior designer), you don’t have many options.

However, if clients are used to you being in one place but providing the service doesn’t depend on it, becoming location independent is going to be much less of a big deal than you anticipate.

I’ve heard from countless people who’ve made the leap that clients just don’t care: if they enjoy working with you and the service doesn’t suffer, it makes no difference to them whether you’re in your home office in Kendal or a co-working space in Krakow. And when you sign up a new client, it’ll just be normal to them that you move around. They’ll likely be fascinated, and ask you lots of questions about it. But if they don’t like it and that’s a dealbreaker for them, they’re probably not the type of person you want to work with anyway.

The cost

There are three main factors that determine how much a location independent lifestyle costs:

  1. Where you travel to
  2. How you handle your “home base”
  3. How long you stay in one place

Where you travel to

Obviously, if you want to spend time in New York and Paris it’ll cost more than if you choose to base yourself in Vietnam and Thailand. This is something you have full control over, and if your income is variable you can strategically switch locations to save more or splash out.

How you handle your “home base”

We’ve used three different models for accommodation, which I’ve broken down in full here.

For a good few years, we didn’t have a home in the UK that sat empty while we were away. So, given that the majority of other countries are cheaper to live in than the UK, travelling worked out no more expensive (usually cheaper) than living in London full-time. Even after factoring in short-term accommodation in (say) Spain being more expensive than a long-term rental, plus costs like flights, it still tended to come out evens.

Now though, for convenience we do have a home in London. So whenever we’re away, we’re paying “double rent” – and even “double gym”, and other things that aren’t worth cancelling because we’re coming back a couple of months later. That makes things expensive.

How long you spend in one place

As well as obvious costs like flights, there are non-obvious “getting set up” costs when you arrive in a new place – like re-buying items you can’t travel with but can’t live without (a foam roller is one example for me) and doing a big grocery shop.

Obviously, the longer you spend in each place the less frequently you’ll encounter these switching costs.

So to keep the cost as low as possible…

  • Adopt a travel pattern that makes a home base unnecessary, or keep it but offset some of the costs by renting it out on Airbnb (or similar) while you’re away
  • Move around less frequently to reduce switching costs
  • Choose locations strategically: go to expensive places off-season (like Barcelona in February rather than July), and follow up a stint in a costly location with a move to somewhere cheaper

School

If you have kids, this is likely to be the most obvious barrier. Given what a big deal this subject is, this section is going to be surprisingly short. That’s because there isn’t some magical answer you haven’t thought of. The options are pretty obvious, but let’s run through them quickly.

Firstly, remember that “location independent” doesn’t mean that you have to travel non-stop. As long as you’re not tied to one location for any other reason (most commonly a job), you’re free to travel as much as you like outside of term time – which turns out to be a large amount of the time.

Go off on a two month adventure during the summer, have a couple of weeks away somewhere warm over Christmas, another couple of weeks over Easter, and a few little trips away during half-term breaks. Before you know it, that’s more than a third of the year away!

Yes, prices are higher during times when everyone else can go away too. But that’s your trade-off. And you’ve still achieved a decent amount of flexibility without having to do anything radical in terms of schooling.

If you do want to do something more radical with schooling, then of course the options open up much further. Home-school your kids, and you can go anywhere at any time. Do you want to do that? For most people probably not, but it’s an option – and it’s easier now than ever before, because there are so many homeschooling networks and groups for parents to share resources and ideas.

I was going to say that it all comes down to your priorities, but giving your kids the best start in life is going to be the top priority for almost everyone. In fact, it’s more about your worldview and the personality of your kids. If you believe that stability in a good local school is what’s best for your child, that gives you certain constraints but still a fair bit of flexibility outside term time. If you believe that new experiences and adventure are what matters most, you’ll be able to pick from all kinds of wild options.

Dependent family members

I actually think this is the hardest item on the list. You can find a solution to earning money, finding out where to stay and dealing with paperwork…but what if you have ailing parents who depend on you? Or a new grandchild who you want to see and help out with?

The first thing to assess is whether you really do need to be around, or if you just believe that you do. I’ve heard from quite a few people who feel obligated to be around for family members and put their needs first, but there’s no reason why they couldn’t have more flexibility if they were a bit more selfish.

I don’t mean “screw you Mum, you can get the damn bus to your chemo appointment”, but maybe sharing the responsibility more evenly across siblings or finding other solutions.

If you really do need to be around for family, then you do. But still: if you can remove some of the other barriers, you might be able to get away for more short trips than you currently do. Or by sorting out the money aspect, you could be less tied to an office and use your flexibility to be around for family more while also having more time for yourself.

A reluctant partner

Another tricky one. It’s not so much of a problem if your partner doesn’t share your appreciation for vintage cars of the movies of Bradley Cooper, but it’s a bigger deal if you want to backpack around the world and they don’t like venturing beyond your local pub.

First off, try to get them on the same page as you. If you’ve had your eyes opened by certain books, blogs or podcasts, see if they’re willing to read/watch/listen to some of your favourites to get a sense of what you’re so excited about. Maybe after that they’ll get hooked too – but if you’ve been absorbing this material for longer, it’s natural that it will take your partner a while to internalise it and get to the same level of excitement that you have.

Another useful step is to exercise what all good relationships come down to: communication and compromise. Even if your partner doesn’t have the same travel ambitions you do, most people would welcome at least a bit more freedom and flexibility.

Talk about what they might want – which could be more weekends away, the flexibility to go on outings mid-week when popular attractions are quieter, or the ability to go visit family members for a couple of weeks at a time rather than squeezing it into a few days.

If you can sell them on the vision of being able to do the things they want, they’re more likely to buy into making the changes necessary to make them possible. Then once you do them, they might get a taste for taking it further. Or they might not, but at least you’re closer to what you wanted than you otherwise would have been.

It’s also helpful to dig into the objections they have to travelling more, so you can explore how they might be overcome. For example, they might value having routine, and lots of friends nearby. You can then explain how staying somewhere for a month or two is enough to develop a new routine, and all the ways you can meet new people – while still not being away long enough for old friends to forget you.

Ultimately, location independence does involve trade-offs: it involves giving up some convenience and certainty (among other things) to gain flexibility, excitement and new experiences. If you’re not aligned on which of those sides weighs the most heavily for you, you might never get to a point of total agreement – but if you communicate well, there should be somewhere in the middle that you can meet.

Friends

You can split this into two: the worry about losing old friends, and the challenge of making new friends.

When it comes to old friends, how much of a concern this is comes down to how often you go away and how long for. When we started out, we were away almost permanently – and yes, we fell out of touch with a lot of friends. It’s the biggest (possibly only) regret I’ve got from doing what we did…but on the other hand, the friendships that lasted were obviously the ones that turned out to be strongest, so you could just see it as “pruning” rather than losing friends.

If you’re only popping away for a couple of months at a time, it’s less of an issue. In cities like London at least, everyone seems to be so busy and working so hard that they don’t see friends that often anyway: you might have relatively close friends who you only see once a month, and just keep in touch with by messaging in between. You could probably go on a pretty lengthy trip without them even noticing.

What you will lose is more casual friends and acquaintances, if they’re linked to activities that you won’t be able to participate in anymore. For example, if you have to cancel your gym membership because you’re away half the time, you won’t see your friends from the gym. Ditto football teams, parent-and-baby meetups, and other regular-but-casual parts of your routine that will get lost.

How much of an issue this is for you will depend on your personality. Because I’m an introvert, I prefer to have a small number of good friends rather than a larger number of acquaintances – and if I go through most of my day without talking to anyone because I don’t have acquaintances and don’t even speak the language, it doesn’t bother me. If you’re an extravert who gets a lot of energy from having quick interactions with familiar faces throughout the day, you’ll probably struggle more.

Making new friends

No two ways about it: I’ve found this hard. Everywhere you go, people will have their friendship groups already – so why should they go out of their way to get to know someone who’s only going to be around for a few months?

The only thing I’ve found that makes this easier is networks based around interests. For example, I’m a member of an entrepreneurship community that has members all over the world. In most major cities, I can either attend one of their events or seek out individuals who live there. Joining some kind of local club based around a specific interest would probably help in the same way – especially if it’s geared towards expats, because they’re used to people coming and going.

A final thing to think about relating to friendships is your kids: how will they make friends? My own isn’t old enough for this to be a concern yet (he’ll happily chat away to a piece of paper if you draw a smiley face on it), but I’ve been told by travelling parents that children are great at making new friends in almost any situation. Of course, it depends on the personality of the child, so if yours are more reserved you might need to put more thought into this.

Hobbies

I heard from a reader who said that it might sound silly, but he’s a keen swimmer so access to a 25m pool would be a deal-breaker for him.

That doesn’t sound silly at all. Hobbies are important: if there’s something you do every day or every week that makes you happy (especially if there’s a social aspect too), it’s going to be a wrench to lose it.

There are a few ways to make this easier.

The first is to base yourself in larger cities, where there will be groups for everything you participate in at home and access to all the facilities you need. Most major cities have strong expat communities, with at least one Facebook group or other forum that serves as a hub. If you pop in there and ask if anyone knows a climbing wall or if there’s a netball team or poker game you can join, someone will probably have the answer.

The next is to base yourself somewhere for a longer period of time. It takes time to settle in somewhere and find out what’s going on where, and if you’re only there for a month it might not be worth it. For three or six months though, it might still take you a month to settle into a new routine but you’ll have plenty of time left to enjoy it.

Conversely, the other option is to go away for shorter periods of time. Being location independent doesn’t have to mean long trips or long haul. If you just want to have more week-long trips than a normal job would allow you, that’s fine: you can keep all your hobbies going at home, and still enjoy getting away. We did this when we were tied to London for medical treatment: whenever we got the opportunity, we’d just go elsewhere in the UK for a long weekend or pop to Spain for a week.

Finally, you can get new hobbies. For example, I love going to the gym, but for the length of time we’re away it’s a real pain trying to find somewhere with the right equipment (why doesn’t everywhere have a squat rack?) that doesn’t require a long contract. So I’ve developed a bodyweight strength routine I can do in our apartment, and supplemented it with running – which is a great way to explore a new city.

Clearly that isn’t going to work in every situation, but it’s worth assessing whether a particular hobby is important for your happiness or you just enjoy the comfort of having it as part of your routine. Again, it’s a trade-off: would what you gain from travelling be more than what you’d lose, or not?

Finding short-term accommodation

For years before Airbnb came along, we were racking our brains for how we could spend six months in NYC. A six month lease with no credit history seemed impossible, and so did affording a six month stay in a hotel.

Aside from advances in communication technology, Airbnb has probably been the biggest factor in making this lifestyle possible. Sadly though, it’s not as good an option as it used to be.

As Airbnb has become more popular, prices have gone up. It used to be the case that renting short-term in most cities would cost us the same as renting long-term in London, on account of London being so expensive. Now though, while it’s not hotel-level pricing, it can cost a lot more.

So what can you do?

Airbnb still has the biggest choice and the platform makes it the most convenient, so Option 1 is to just deal with it and cut your cloth accordingly. It might mean living somewhere smaller or less central than you’d ideally like. It might even mean restricting yourself to cities that have a lower cost of living (but are still amazing) like Budapest or Lisbon.

Option 2 is to dig deeper in search of bargains. In every city there will be local marketplaces that aren’t geared towards tourists, so the prices tend to be lower. Of course, if you end up dealing directly with an individual rather than going through a platform like Airbnb you’ll need to exercise more caution.

And Option 3 is to spend a longer amount of time in a given place, so you can play in the long-term rather than short-term rental market.

Some people choose to book a week or two in an Airbnb, and use that time to scout out other local options. This makes a lot of sense: it’s much easier to find somewhere when you’re actually there.

As is becoming a theme though, we value convenience (i.e. we’re lazy) and just pay Airbnb prices.

Tax

I hate writing about this subject, because I don’t know enough and there will always be someone to say “but what about…”.

So: this is not tax advice, I’m not telling you what you should do, and I’m not telling you what I do. These are just options to explore.

The easiest option is to just continue to pay taxes in your home country as if you’re there all the time, earning all your money there. Should you technically be paying some in the country you’re staying in while you earn it? Maybe. Probably. But that’s just not practical if you’re constantly moving between different countries, and you get to feel like you’re still “doing your bit” somewhere.

Another option is to use your location independent status to reduce or eliminate your tax bill. A common scheme is to run all your income through a company that you register in a country with a 0% corporate tax rate, and establish your own residency either nowhere or in a country with a low personal tax rate. Be aware though that shaking off your home residency isn’t easy: it usually takes more than just not being there for a while.

Then there’s the option of paying tax in multiple countries, which might be possible if there were just two or three countries you flit between.

There will be other options too. As I said though, I don’t know what you should do. I do know, though, that you shouldn’t let uncertainty around tax hold you back from living the lifestyle you want.

Admin and paperwork

It annoys me in principle that so many “official” tasks revolve around sending and receiving slices of dead tree when we clearly now have a better way, but in practice it isn’t an issue all that often.

How to handle paperwork deserves an article in itself – and will get one – because it depends on whether you have a home base, among other things. If you’re only ever away for a few weeks at a time, you can probably deal with just letting the post pile up and deal with it when you get back. If you’re away for months (or permanently), you’ll need a better solution.

What we do is get as much post as possible sent to a virtual address, where it’s scanned, uploaded and emailed to us. Most companies are OK with this, but some will only send to your actual home address. There’s not much that can be done about that, and in any case it’s useful to have some things going to your home address so you can use them for proof of identity.

When it comes to signing documents, a lot can be done digitally but – again –some financial institutions that dragging carbon across dead tree gives cast-iron proof of your identity in a way doing the same thing digitally never could. There have been situations where I’ve had to print documents, sign them and post them back from abroad, which is inconvenient but not impossible.

In short, it’s an annoyance, but it’s something that can be figured out.

Summing up…

I’m sorry if you were expecting easy answers to any of these. I’ve given you some pointers, but ultimately in each of these areas you’ll have to weigh up the trade-offs and find an approach that works for you.

When you decide to reconsider something as fundamental as where and how you live, every part of your life becomes an experiment. And that’s exciting! For anything you encounter, you can:

  1. Generate a list of all the possible options (more than you think!)
  2. Pick the best-sounding one to start with
  3. If it doesn’t work for you, reflect on why
  4. Use this knowledge to make a better choice next time

A recipe for an easy life? No. But so much more interesting than just accepting the defaults.

Your turn!

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