Interview with James Cave

portugalistJames Cave is a freelance writer at Portugalist. You can find him in Facebook, Twitter, and Instagram.

1. How did you start working remotely? 

About 7 years ago, I decided to make the switch from office worker to “digital nomad”. I’m not sure if I was aware of the term at the time: I just thought of myself as a freelancer who travels.

I’d planning on writing ebooks but, pretty soon after making the switch, I ended up managing the online marketing for a growing startup which put me in more of a remote role than a freelance role.

I was very nervous about making the switch, and being able to make ends meet, and must have put it off for at least a year if not several. To keep my costs low, I started off by house sitting and looked after other people’s pets while they were away on vacation. For the first year, I looked after several homes across Europe including a farm of 18 alpacas in the South of France. As I started earning more money, and having less time for house sitting, I switched to renting through sites like Airbnb.

2. What do you think are the main advantages of remote work?

Being able to work remotely means that you don’t have to make a choice between your career and taking time off to travel. Having a remote job is also much easier than setting yourself up as a freelancer and having to scout for clients.

I’ve also been able to save quite a bit of money my living in countries where the cost of living is lower, and that’s always something that’s appreciated.

3. Do you think there are disadvantages or that you’re missing something by working remotely?

As an adult, one of the easiest ways to make friendships is through the place that you work. Although many companies with remote employees will have regular staff parties, it’s really not the same.

I usually join the local meetup for digital nomads and freelancers when I’m in a new place but, because remote workers and digital nomads are so transient, it can be a difficult place to make really good friends.

It’s not impossible: Some of my best friends are also remote workers and we meet up around the world, but it does take a lot of work to make those friendships.

4. From which cities or countries have you worked since you have become remote? 

I’ve lived in several countries in Europe including France, Spain, Portugal, and Germany, and worked from countless others both in Western and Eastern Europe. I’ve also travelled around SE Asia, South Africa, and parts of North America.

I love Portugal (hence the blog about Portugal) but two places that I would like to spend more time are South Africa and Mexico.

5. From which type of place do you prefer to work? 

I usually work from home. If I had to choose between coworking spaces and coffee shops, I’d definitely say a coworking space. It’s just a much easier place to go and get work done without feeling awkward about how much coffee and food you should be ordering.

6. Which places would you like to travel to while working remotely?

I’ve been meaning to take a trip to South America ever since I started doing this, so that’s definitely on the cards.

Before that, though, I have a big trip planned around Portugal. I need a lot of content for the website about places like The Azores and the North of Portugal, so I’ll spend some time working from places where I imagine very few nomads go.

7. What would you say to the companies that don’t believe in hiring employees who work remotely?

Whether you’re working from home or from another country, being able to work remotely is not something anyone will take for granted. Knowing how valuable this is, I find that I work much harder than I did when I was in an office environment. From speaking to other remote workers, it seems that I’m not the only one either.

8. Which tools do you use to work remotely?

I mostly get by with e-mail and Skype. It really doesn’t take a lot of tools to work remotely.

Certain companies will have tools that they use (Asana is very common at the moment), and I’ll use whatever tools they use, but, personally, I try to keep things simple.

9. How do you manage your business and taxes as a remote working professional?

I pay my taxes the same same as I would if I was based in one place. It’s a little harder to keep all your receipts when you’re living out of a backpack, and I do have to be aware of where I can and can’t work on certain visas, but the actual bookkeeping is more or less the same.

10. What advice would you give to people looking to work remotely and companies making the remote switch?

I’ve heard of some companies that allow their staff to work one month of the year in another country. This is quite a good compromise and a good way of allowing both the employees and bosses to test the water and figure out what all the potential problems are.

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