More companies embrace remote work. But it’s not all glamorous and perfect as it may look from the outside.
I’ve been working remotely for over five years now and can tell you that there are ups and downs just like working in the office environment. However, more people choose freedom and adventure over security for a reason.
To help you better understand remote work and digital nomad lifestyle I reached out to prominent remote work evangelists and experienced nomads.
Meet the experts
Amir Salihefendic is CEO and founder of Doist, the company behind #1 productivity app with 13M+ million users, and Twist, a new (asynchronous, thread-based) team communication tool. Doist is a remote-first company with 50 team members who represent 20 different nationalities that creates products that help people live more fulfilling, balanced lives.
Diego Bejarano Gerke has a fascination for intentional communities. He’s a co-founder of WiFi Tribe, a community of nomadic professionals who live, work and travel the world together.
Tal Gur is a blogger, lifestyle entrepreneur, and devoted adventurer who has spent a decade pursuing 100 major goals around the globe. Find out more about Tal and his 100 life goals project at Fully Lived.
Jamie DeBole is the co-founder and CEO of GlobeKick, a company that helps digital professionals create meaningful connections while traveling the world. An avid traveler and entrepreneur, Jamie has traveled through 31 countries while co-founding 3 companies.
Hailley Griffis focuses on sharing Buffer’s Future of Work efforts and runs Buffer’s publication focused on transparency and workplace culture, the Open blog. Like the rest of the Buffer team, Hailley works entirely remotely.
Dave Nevogt is the co-founder of Hubstaff which helps virtual teams communicate better through automatic time tracking and activity tracking. He’s been running online businesses since he was 23, and now manages a team of 30 remote employees.
Martin Studencan is an entrepreneur, remote worker and boardsports enthusiast. He is a founder of Remote Workers community, co-founder of award-winning medtech startup STEMI and founder and CEO of Wolfhouse which offers unique off-site venues and retreats for teams, groups, and entrepreneurs.
Fernando Mendes was born in Portugal and started is first coworking space in 2011. Today he lives in Mozambique where he runs 4 cowork spaces in Maputo and hosts pop-up cowork experiences for remote workers on Mussiro.
Dean Leibowitz has spent the last 12 months developing and overseeing Selina’s cowork products and has been with the company as they have now opened 16 new locations.
Dave Abraham is the co-founder of Outpost, a coworking/coliving community with locations in Bali and Cambodia. Previously, Dave worked on Wall Street, in the White House budget office and at a non-profit based in Uganda.
Stuart Jones is the founder of Coworkation. He has lived a location independent life for the past 15 years.
Maria Kinoshita is a global citizen with roots in Africa, Japan, and France, but calls Canada home. She is the founder of Octo D, an ed-tech startup that focuses on B2B multilingual eLearning module development.
Chuck Melber has been honing his skills as a digital nomad for the last five years. Right now he runs marketing at Nomad Goods.
Andrew Henderson is a world traveler, investor, entrepreneur and founder of Nomad Capitalist. He is helping young entrepreneurs create their nomad strategy, set up foreign bank accounts, move their business overseas, obtain the second passport and invest in foreign markets.
Sairee Chahal is founder and CEO of SHEROES, the largest women’s growth network. An entrepreneur at heart, she is passionate about women’s progress and development.
Christopher Dodd is a blogger and social media influencer who writes and creates videos about the digital nomad lifestyle through his YouTube channel and blog, Chris the Freelancer.
Sergio Sala is a self-taught web designer sharing his vision, of independent work & living anywhere, on a weekly basis to his newsletter of creative nomad readers.
Uwe Allgäuer is a real estate manager, Coworking Banskoowner, entrepreneur, consultant, mentor, and skipper.
Tomas Laurinavicius: What is the biggest challenge remote workers face today?
Fernando Mendes: One of the challenges is still to find more jobs that allow you to be working remotely. Although the remote jobs are growing rapidly, remote workers are growing at the same pace or higher. The mentality to transform “normal” jobs into “remote jobs” is still the biggest challenge we face, but the trend is there and I would say it is unstoppable.
Then you have specific challenges depending on the type of remote worker you are. If you are a nomad and enjoy spending your time in different countries for a while there is still the challenge of working visa vs tourist visa. Thailand was the first country that recently issued remote workers visas, kudus to Thailand. So a remote worker from the US, or France, living in Thailand for one year, but working with clients in other countries, can stay legally in Thailand with a proper remote worker visa and pay taxes in Thailand.
Dave Abraham: Their expectations. Traveling and working introduces working challenges. Many are expected: time differences and distance from colleagues are obvious. Less obvious are the social challenges. Developing a new support network of people when traveling from place to place is not easy or quick. Gone are those folks who you have gone through meaningful experiences together – think university and jobs. Those connections are what social lives are built upon. Realizing that will go a long way to make your transition to remote work easier.
Stuart Jones: I would say that the biggest challenge, but is also an exciting opportunity, is how remote workers and location independent professionals can optimise the freedom that they have to live really extraordinary lives. A larger degree of freedom to work from where and when they want gives an opportunity to design lifestyles in unique and creative ways. Routines, timetables and life systems can be structured in a way that is tailored to fit your needs and interests. Life can be lived more holistically, taking into account all facets of your life. Lifestyles can be created enabling you to live closer to your passions, you can live in a more balanced way, and get more out of life. But this does not happen automatically. It requires constant thought, trial and error, and the flexibility to adapt.
Maria Kinoshita: The biggest challenge facing remote workers today is understanding from the external world. I spend lots of time telling friends and family: no! I’m not going on vacation AGAIN, I’m not a millionaire, I will be in touch. I would say the hardest part is to have our customers understand us. I am not a typical remote worker. My team is 100% remote, most of us are nomadic at different lifestyle levels and my business Octo D works with major corporations. Some remote workers would hide from their clients but we actually are very open about it. When we start working with a client, as soon as we have the chance, we talk about our values and lifestyle. We get some initial apprehension, but in the end, they realize it’s not a problem. Our clients can even enjoy the fact we are in different time zones as it makes us very reactive.
Travelling while working presents personal challenges. You are constantly surrounded by places you want to discover, people you want to know, and faced with logistics that need to be taken care of. It all that can lead to procrastination from work and focus can be a challenge, at times. I slowly eliminated every technical issue that prevented optimal workflow while traveling. I bought a gamer mouse and a secondary portable screen using online management apps. With these improvements, I’m able to do long stretches of work. Parts of my routine that I would do at home are easily replaced by having a long chat with a local or a 30 min walk to the grocery store or market. Speaking of walking, having a workout routine or eating healthy can be challenging for the first weeks you visit a new place.
Chuck Melber: The biggest challenge for remote workers today is the lack of a personal connection with their team. Despite the growing popularity and acceptance of remote work most offices are still locally staffed with just a couple remote workers. This lack of in-person interaction can slow projects down or cause unnecessary friction until the team establishes a rapport with one another. This is especially true as new team members are added to the home office having never met parts of the remote team.
Tomas Laurinavicius: How remote work will look like in 2018?
Tal Gur: In 2018, remote work will become more accessible and even easier to manage thanks to technology and collaboration. More Millennials will join the ranks of location independent entrepreneurs and the traditional education and career paths will become even less effective.
Jamie DeBole: According to the 2017 Global Coworking Survey by DeskMag, 45% of freelancers and remote workers in coworking spaces spend one or more weeks per year abroad for business. The survey also showed that nearly 13% of coworkers consider themselves digital nomads. I expect to see this trend continue in 2018 as more remote workers look for ways to gain even more freedom in how and where they work.
Out of this change, we’re also going to see companies being more thoughtful in how they incorporate remote work programs into their employee benefit packages. Companies will continue to treat remote work as a perk, but start to consider it a professional development opportunity for their employees when coupled with travel for a few weeks or up to a month. Employees who have traveled to other countries are more likely to be self-starters and creative problem solvers. They’re also generally more adaptable to changes in the organization and require less day-to-day management and oversight.
Hailley Griffis: There will be a growing number of resources, programs, retreats, and coworking spaces available to remote workers. There’s a huge shift to more people working remotely and trends show that remote work will only increase in 2018. With this larger number of remote workers, I think more people will be seeking to be connected to like-minded individuals and the number of programs and spaces will rise as a result.
Dave Nevogt: Rates will rise for people outside of the US as companies as more and more companies are looking for great talent all over the world and communication becomes easier based on technology. More skilled professionals around the world will leave corporate offices where they are working for one employer, opting for a freelance environment instead because they can charge more and work a more flexible schedule.
Amir Salihefendic: It’s going to be a long, uphill battle: Calm, asynchronous communication in remote work isn’t the norm. It’s going to take a major shift in thinking to recognize that focus and balance are vital assets that companies need to protect in order to be successful. But we hope 2018 is the year that people are finally waking up to the fact that Slack and group chat is absolutely killing their productivity (and is especially problematic for remote & distributed teams).
Diego Bejarano Gerke: It will seem like a marginal change from this year, as I do not predict the ‘big boom’ to happen in 2018. However, there will be more coworking spaces popping up around the world, as well as more co-living spaces, and everything in between. In terms of the nomadic co-living groups, I believe there will be a few larger players in the space, lots of recent entrants will close down again (as we saw already in 2017) and it will become increasingly difficult for new co-living groups to establish themselves in the space. There is now significant diversity (options), reputation (years of running), and funding in many of these groups, which will make it difficult for new entrants to compete.
Throughout 2018, we may see a few niche companies attempting to enter the space, but it’s still too early for them, as the pool of remote workers needs to be much larger to carve out a very precise niche. Expect a lot of this a few years down the line.
What we will see, is a lot of hostels trying to accommodate for remote working backpackers, with Selina leading the way in Central and – more and more in 2018 – in South America, with their aggressive expansion.
Airbnb has launched an initiative to highlight adequate houses for working remotely, so this is also something that we can expect to see more of in 2018.
People will seek out the community as they travel more permanently. They will aim to find a way to replace the communities they were part of at home with an on-the-road community. They will find this in local coworking spaces, online with Nomad List (#Nomads), or in traveling communities.
Martin Studencan: More businesses are required to offer more flexibility to its workers. Companies that will resist, might be affected by higher turnover rates. The increase in self-employed individuals is the result of the world we live in – gig economy, characteristic by short-term contracts and freelancers. A lean entrepreneur will ‘lean more on’ Fiverr or Upwork, and the rest is fighting for gigs. Higher quality work is rewarded by better reviews and more work.
The large sum of people, including me, are comfortable working from coffee shops, I estimate that pubs and coffee shops will soon adjust to becoming more like coworking spaces, offering laptop friendly areas and vice-versa. On another side, coworks adding spaces for socializing and boosting revenue by upselling drinks. The line between 2 blurs.
Startups are losing the fight for top talent with big players like IBM, Facebook, Google. They can’t compete on financial compensation level, but what they can fight with is company culture and offering more flexibility, allowing team members to work remotely from anywhere in the world.
Tomas Laurinavicius: What are the rising hotspot destinations for remote work?
Andrew Henderson: It should come as no surprise to anyone that knows me that I’m a big believer in Georgia. The country’s capital, Tbilisi, has so much potential. As a remote working destination, it could be the next Berlin. Honestly, I hope it’s not because I like to keep it as my little secret, but I own a lot of properties in the city center so it could be very good for me financially to have more people coming into the country, but I’d still like to keep it to myself.
Tbilisi is so laid back, so calm, and so different. You can try and compare it to any other place and say that it’s kind of like this or that, but it’s like nothing else you’ve ever seen. People are just beginning to go there. Everything is incredibly cheap, the people are so warm, there’s great food, fantastic wine, and you now have an Impact Hub and a local co-working space. There are challenges there; for example, if you’re not used to smoking, everyone smokes there. But there is a good chance that you’ll have the next Berlin in Tbilisi, Georgia.
Malaysia is another great example of a place that is doing a lot of beautiful things. It has an aspiration to go from an emerging country to a developed country in the next decade or so. Malaysia is a hidden gem and now they have some co-working spaces, including one in my old building in the city center right next to the Pavilion Mall in the ViPod Suites Residences. Malaysia is finally coming up as an alternative to Bangkok with all the co-working spaces and great infrastructure. Plus, Malaysia is so much more civilized than anywhere in Thailand and it is much easier to get into for long-term stays.
Lastly, Colombia is a great place for living that some people are already aware of in the remote work community. More folks go to Medellin, but I prefer Bogota because it has that capital city, international vibe. As a whole, Colombia is easier to deal with than a lot of other places and it’s even easier to get your visa there for the next place on your route. It’s an amazingly livable city. It doesn’t have quite the potential as Tbilisi or Kuala Lumpur, but it’s really coming up. In fact, Colombia is going to be one of the top (if not THE top) free economies in South America in the next ten years. There’s a lot of potential there.
Despite my preference for nice accommodation, I also prefer to get off the beaten path to find economies that are on the rise. That’s why a place like Portugal doesn’t appeal to me as much. I like Portugal, it’s gaining a lot of traction in the western world as a borderline first-world country, and they are doing a lot of things right to attract people. I love the country, but I’m not sure Portugal is heading up, at least historically speaking.
People are certainly going to Portugal and it’s a very nice place, but the challenge I’m looking at is finding the places that have the infrastructure without sacrificing potential growth. In places like Portugal and Spain, you go to restaurants and you wait around a long time, they don’t always take your credit card, and some restaurants and cafes don’t have Wifi. Worst of all, they are complacent with this type of behavior.
I’m looking for efficiency and those kinds of inconveniences lead to the exact opposite. As people start to make more money while they work and travel, they’re going to want efficiency as well. That’s why I look for countries that are smaller and a little bit off the radar that are making an effort to get on the radar. Malaysia and especially Georgia have done that in an amazing way.
In summary, Bogota, Kuala Lumpur and Tbilisi are my top remote work destinations. They are places where I am going to be spending a lot of my time in the next year and I wholly recommend them to others looking for a great experience working remotely.
Sairee Chahal: Co-working spaces in India are really picking up because they are not just spaces to work without the distractions but hubs to network and seek out potential employers/ collaborators. India recently even got its first co-working space specifically for women, to create an ecosystem of support for women who work as freelancers, consultants, or are foraying into entrepreneurship.
Christopher Dodd: Locations like Chiang Mai, Bangkok and Bali in Southeast Asia have been popular hotspots for years now but I think in 2018, we’ll start to see destinations like Medellin, Colombia, Budapest, Hungary and Las Palmas, Gran Canaria rise in popularity.
These destinations are more expensive by comparison but offer more in terms of time zone and business opportunities. While the remote workspace has been traditionally dominated by individuals, we’re now seeing entire companies move out to these locations in greater numbers.
Dean Leibowitz: In previous years, I would say a lot of Asian destinations like Bali in Indonesia and Chiang Mai in Thailand have been the major destinations for this type of work, but Medellin, Colombia can’t be far behind and if anything will eventually take the cake. An eternal spring, amazing food, is highly affordable and best of all has an amazing array of coworking spaces and a bustling digital nomad community and local entrepreneurship scene.
Sergio Sala: Maybe I’m biased as a proud Mexican, but Mexico is the next place to be. We have cities like Playa del Carmen where the colorful beach and bright parties are attractive. And in the other side, places like Mexico City (nominated as one of the best cities to see in 2017) gives the chance to eat good food but also live as cosmopolitan.
Also, one of the hottest spots right now is the beautiful city of Medellin, where besides its amazing coffee, there’s a great scene of international events, businesses and of course, parties.
Uwe Allgäuer: At the moment, two places are still very popular: Chiang Mai (Thailand) and Bali (Indonesia). Both places offer an amazing environment for all groups of location-independent workers but they also embody “success”. What I mean by that is that people who have managed to live in either of these places for let’s say at least three months have the feeling that they are part of the global community of digital nomads, location-independent entrepreneurs and/or remote workers! Many people correlate the new work lifestyle with Chiang Mai and Bali but as other locations open up or become more recognized among the community, these two places might lose their “hotspot” tags.
Countries in Southeast Asia are common destinations for remote workers. They offer good and healthy food, affordable accommodation, thus keeping the burn rate low, and Asian people, if I am allowed to generalize, are usually very welcoming. Also, many of the countries in Southeast Asia are solo-traveler friendly.
However, I think many places still need to be discovered. Bulgaria, for instance, represents a European country with an easy and welcoming legislative system that allows people to incorporate a business not only very easily but also very affordably, and also offers very low taxation rates. They are very good reasons to establish a base in Bulgaria, especially if your customers are based in similar time zones.
Tomas Laurinavicius is a lifestyle entrepreneur and blogger. Join Life Designed, his weekly lifestyle design newsletter.