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Travel and Work Remotely – What Are the Options?

It wasn’t easy finding the silver linings during this pandemic, but one welcome trend made huge leaps forward: the ability to work remotely instead of commuting to an office. I’ve been a location-independent remote worker since the early 2000s, but I’ve long been an oddball in that respect. People used to look at me funny when I said I had a “laptop job.” They were skeptical that I was really making money online in the same location where they were spending a fortune on vacation. 

work remotely

Now working remotely is normal, part of the mainstream. Some big companies have dialed back how many remote workers they are allowing to stay at home (wherever that may be) or are going with a hybrid approach. Others saw that productivity actually went up, not down, however, so they’re ending leases and shutting down physical offices.

In some cases, companies have gone fully remote—or started out that way and kept the set-up as they kept growing. There are companies with hundreds of employees now that don’t have a physical headquarters. 

Then there’s the set-up that I chose from the beginning that has also grown in popularity: running your own business online. In every way I can think of, this has gotten far easier than it was when I started out doing it nearly two decades ago. For free or close to it, we can make phone calls, share large files, and collaborate on projects with anyone around the world. We can hire someone for a task not needing to care where they live.

On top of it, advice on how to start and run a business is easier to find than ever, from people who have already done it and succeeded. Podcasts, blog posts, books, courses—it’s all out there for anyone who wants to take the time to learn. 

If you’re stuck in a physical job but you have the skills and the passion to go beyond that, there’s never been a better time than now to make the leap. Just be advised that starting any kind of new business, including a blog, will take years to start generating solid income. There are easy options for filling in that gap though while still traveling the world or living overseas. I’ll go over those in the remote business section, but first the location independent jobs options. 

Location Independent Jobs and Remote Working

Many people have no business starting their own business because they’re not cut out for that. They don’t want all the risk and the stress of making it work on their shoulders. They want to get paid for their time and then shut the laptop at a set hour and be done with it. There’s nothing wrong with this: we need these people for the world to function. 

In the olden days, this usually meant they needed to show up somewhere, punch the clock, and then go home. Corporate jobs involved a commute in a car or subway, as did jobs that require a physical presence, such as medicine, police, firefighting, and retail stores. The latter type will never go remote unless someone figures out how to launch Robocop (with no adverse side effects) or invents flying drone fire engines controlled from a laptop. If you need surgery, you probably want a surgeon to be right in front of you. 

For the vast majority of “white collar” office jobs and less glamorous sales and customer support jobs, however, being physically together has few upsides and a lot of downsides. There’s very little benefit to having everyone spend massive fossil fuel resources and countless hours of their time showing up at the same building every day. Managers love to tout the benefits of collaboration and idea-sharing, but in practice this usually just means more boring meetings that waste most peoples’ time. It means distractions from co-workers barging into your cubicle when you’re trying to get real work done. If you’re good at your job and self-motivated, you get more done when working remotely

working remotely living abroad

Whether they want to admit it or not, what most executives found out over the past two years is what we knew they would find out: good people get more done if you give them clear goals and just let them do their job, on their schedule instead of yours. It turned out they didn’t need so many meetings after all. It turns out A and B players don’t need a manager looking over their shoulder to get great results. (If you’re a manager who is not seeing great results from remote workers, maybe it means you’re only hiring C and D players or your pay levels are not competitive…) 

So here we are now, in a world where many jobs that weren’t remote before now are, even from the biggest corporations. Then there are all the jobs with small businesses and start-ups that are remote-only, open to anyone living anywhere who can do the job effectively. 

So you could go totally broad and search the likes of,, or any of the other massive job boards. Or you could find the site for whatever skill you specialize and sort the jobs by ones that are remote only. For writers, for instance, that would be sites like and Most industries have some kind of focused site like this. Beyond those though, there are some better options where you don’t have to do any sorting. 

Where to Find International Remote Jobs

If you want to cut down your search time and only look through listings for remote jobs, ones you could do internationally from any spot on the globe, you want to go beyond the typical job boards. You want to visit sites where it’s expected that everyone who applies is going to be working remotely. 

I’ll admit that I’m only casually aware of these because I’m not a guy who’s out there looking for a job myself. I’m set with my own business. But I listen to enough business podcasts to hear what people have been using, both from the hiring side and the job side. Here are a few to start with, then branch out on your own after that. 

Dynamite Jobs

Founded by the guys who run the Tropical MBA podcast and Dynamite Circle membership group for location independent business owners, this has vaulted to the top with its “remote jobs only” listings. Most of the companies are fully remote and independent, some are growing at a rapid pace, so it’s often a chance to get in with an organization that’s going places. The range of positions here is much wider than on many other boards. 


This is probably the largest remote job site around and you’ve got to pay to use it. You get something for that money though: as with DynamiteJobs, all positions are vetted and there are no scammy listings you can’t trust. They also have jobs listed from Fortune 500 companies, so go here if you want to work for Capital One or Dell without having to get stuck in traffic. 

We Work Remotely

One of the largest remote job sites, this one lists loads of full-time corporate jobs, even up to C-level positions at fairly large companies. Lots of positions in programming, finance, and sales, but also customer support, recruiters, and executive assistants. 


There’s a wide range of job listings in the hundreds of thousands on this general job board, but they have a wide variety of online work from home vacancies, including entry-level jobs that you could pick up to fund your expenses while you develop a client base or get a business going in another area. Also lots of listings in foreign countries. 

Skip the Drive

Extra points for the creative name on this one, plus they go a bit beyond the normal IT and accounting jobs with ones for editors and HR specialists. They also have an “entry level” section if you’re fairly new in the job market.  

Hire My Mom

This is a marketplace for moms looking to pick up remote work and companies that don’t need 9-to-5 types to work on their projects. Some of the jobs are simple virtual assistant affairs, some are coding or customer service. Part-time and full-time. 

Upwork and Fiverr

These are not job boards, but rather marketplaces for freelancers of any type. You post your skills on their and either bid on jobs (with Upwork) or list package prices (with Fiverr) to score deals and get paid. The former tends to focus on more complicated, multi-hour projects, while the latter is used more for quickie one-offs like infographics, creating clips with a video editor by Movavi, or WordPress fixes. Some people have freelanced on one of these platforms for years and then built up enough of a client base that they suddenly had a real business on their hands and had to start hiring others. 

One last note on the job market right now. This won’t last forever, but in the USA at least, there’s still a major labor shortage going on. Partly because we’ve strangled immigration so much and partly because of the economic rebound, we’ve got more open positions than we have people to fill them, by the millions. This is true from the very bottom level to the most skilled positions. There’s not been a better time that I can remember for snagging a job and getting what you want in terms of flexibility on hours and location. 

Running a Location Independent Business

I used to always say, without hesitation, that it’s better to make a job than to find a job if you want to live abroad. But that was before the pandemic turned so many regular jobs into remote jobs. Now it’s not the only path forward for those who want to travel the world and keep working like it once was. For many of us though, it’s still the obvious choice for working remotely without a boss, controlling our time and energy. 

working remotely in another country

There are a few pros and cons to running an online business that I’m acutely aware of being immersed in this location-independent lifestyle for so long. On the plus side, there’s the dreamy part of it that the ads and courses proclaim with their enticing photos of someone working on their laptop in a beach chair or on a hammock. (Pro tip: this scene almost never works in reality.)

You get freedom of time, scheduling, and movement, working where you want and when you want. You just need to find a good Wi-Fi signal and make enough to pay the bills. You can work any hours you want, work whatever days you want, and do it all from anywhere. 

In reality though, almost every online entrepreneur I know works a lot of hours. The promise of a four-hour workweek only pans out if you’ve managed to outsource everything and the business doesn’t really need you anymore. For most of us creatives who are creating content of some kind, that’s not really possible, even if we’re just editing what other people create. We usually don’t mind the work—I haven’t dreaded a Monday since I left the corporate world, but it’s not the chilled-out, relaxed scene the Instagram “look at my dream life!” posts would have you believe. 

The main downside, however, is that it takes a while to ramp up a new business, especially one that’s completely bootstrapped and started from scratch. Unless you’re going to go out and buy a business or website that already has traction, it’s probably going to take you two or three years to start making serious money, even if you do everything right.

So the best time to start a new online business is when you don’t need the income yet. While you have another job, start something as a side hustle, whether that’s a content business, an e-commerce business, software as a service, or some other idea. Once it takes off, then you quit your other job and travel the world. Until then, sock away some money as a safety fund and keep paying the bills. 

The other option is to take up freelancing until your new business gets traction. Apply for gigs on Problogger or other sites for writers, figure out how to be a remote transcriptionist, or apply your skills to be an on-demand video editor. Put a profile on Upwork and start bidding for gigs in your area of expertise. Apply for online ESL jobs.

Figure out how to match what you’re good at with people who are looking for that skill and you’ll at least be able to make enough to get by, especially if you move to one of the cheapest places to live in the world.  

Could You Work Full-time Remote Right Now?

I’ve heard this story so many times that it’s worth repeating here. It usually goes something like this: 

“I liked my job but I wanted to live overseas. I asked my boss if there was a way we could work something out that I could work remotely instead of coming to the office. We did a trial run for a while from my apartment so she could see there would be no problems, then I went fully remote from abroad after that. I’m still working for that company three years later.”

location independent work


There are several variations to this story.  Sometimes the boss says, “No way” and the person goes and gets an identical job with a competitor, with the demand that it must be remote. Sometimes the person transitions to another office in the same company where people are already working remotely. Sometimes the person takes their clients with them if there’s animosity and they get served on a contract basis instead. 

There are plenty of options out there now to work remotely even in your own country. But better yet, you can earn your home currency while working in a foreign country, getting the best of both worlds and using arbitrage to earn in dollars/euros and spend in pesos/rupees/whatever. Work by the beach, work in a fun city, or work with a view of the Andes or Himalayas. It’s now up to you. 


Monday 14th of February 2022

These are great tips considering many lost their jobs during the pandemic. Working at home could be fun too, not to say the convenience of it. Thanks for the links, they are very helpful.

Gipsy Dean

Wednesday 2nd of February 2022

I follow and enjoy your blog and your other Cheapest destination publication but wonder, 'how do you make any money?' I don't see advertisements etc. Do you do this for a hobby and make money another way? Please explain...

Tim Leffel

Thursday 3rd of February 2022

I have many income streams, including other websites, freelancing, and royalties from my books. But yes there are ads on here from the Mediavine Network, so if you're not seeing those you've got an ad blocker on (and therefore are not supporting this site or any others--which leads to paywalls going up to compensate for the lost revenue). As it says in the header, there are also affiliate ads sprinkled in here and there, on gear and travel services. Those generate a commission for sending customers. I also do some ambassador programs and sponsorships with brands and destinations I believe in. More here: