Benefits and Challenges of Workations: A Digital Nomad’s Perspective

Remote working, workation, and living as a Digital Nomad have become huge trends over the last few years. And certainly, earning a living in exotic destinations whilst sipping smoothies at the beach with your laptop does not only sound amazing – I can tell you from experience that it really is!

Yet, as everything in life, this lifestyle comes at a cost. To help you decide whether one of those forms of New Work is something you’d be curious to explore for yourself or initiate within your organisation, here are some of the biggest pro’s and con’s to consider when doing business where other people go on holidays.

New Work Styles: What is what?

Now, before we jump into the juicy details, let’s get clear on what each of these terms actually mean:

Remote work

allows employees to work outside the traditional office environment, for example by working from home or in a co-working space. Usually, when we speak about remote workers, we refer to people who are employed by one company, rather than being freelancers, and who tend to live in a location that is top far away from the company’s office space to physically show up there on a regular basis.


is exactly what is sounds like: A combination of work and a vacation. However, this can mean different things to different people, so if you are considering to implement a new workation policy, get crystal clear on what it means to you and in your company. The range can go from just a week tacked onto the end of an existing holiday to give a team member the chance to work during the day and enjoy the beach and margaritas in the evening, as well as taking some epic social media snaps. Or it could be a few months away in a foreign country, allowing employees to broaden their horizon as they immerse themselves into a new culture without giving up their life at home.

Digital Nomads

are people who earn their living by working online in various locations of their choosing. Personally, I consider myself a Digital Nomad who likes to stay in one location for at least 6-9 months before moving on. This is certainly longer than a workation and longer than most other Digital Nomads stay in the same place. Some might consider me to be more of a remote worker / freelancer than a nomad due to my slow pace of travelling. However, since I do change locations, whether on a regular or irregular basis makes me fall more into the Digital Nomad category. Yet, in the end, all these terms have a bit blurry lines, so it’s always best to define for yourself and be clear with others what you mean by them.

Benefits of New Work Styles

Freedom & Inspiration

I don’t know about you, but freedom is a big one for me. The freedom to choose wherever to work – may it be a specific country, my favourite cafe, or a new co-working space – can provide a strong sense of autonomy and fulfilment. It makes people feel like they are the ones directing their own lives, rather than being directed and often constricted by a specific work location or work hours. This can significantly foster feelings of inspiration and empowerment, which can positively affect their work morale and outputs.

Living in & Learning from Diverse People and Cultures

One of the main reasons for me to start working remotely was to be able to move to places where I could find and connect with a lot of like-minded people – meaning other Digital Nomads and Expats who share the same passions for travelling the world and living life on their own terms. Whilst these people are often other Westerners, you are of course surrounded by all the locals at all times, which gives you plenty of opportunities to not only learn their language, but dive deeper into their culture, history, behaviours and worldviews. This can be challenging at times – especially if they clash with some of your beliefs and ways of working (e.g. the time here in Mexico definitely works differently than in Germany and it’s still something I need to get used to…). However, being a foreigner in a different country somewhat forces you to adopt a curious and open beginners-mindset as you are the guest and you have to play according to the rules that work here. Thus, I find living abroad for extended periods of time an incredible opportunity for truly learning to embrace diversity.

Moreover, living and working abroad for a while is a great way to help break down biases and stereotypes. For example, before I moved to Mexico, I was actually a bit scared because I thought it’s going to be pretty unsafe for me to be there on my own as a young white woman. And whilst I am living in a very touristic spot, I have to say that I feel more safe here than in some areas of Berlin. That was definitely something that I did not expect and that positively transformed my way of looking at less developed countries in general since I question the things that I have been conditioned to believe about them a lot.

Personal Growth

I am 100% convinced that spending time abroad for longer than just a few weeks massively contributes to our development as human beings. Travel allows us to broaden out horizon with the potential of catalysing deep mindset shifts and more holistic worldviews as we are confronted with new people, different places, challenging as well as inspiring experiences. All of them make us more likely to practice our ability to think critically – for example by reflecting on our unquestioned assumptions and culturally conditioned beliefs. Besides critical thinking, the World Economic Forum also states that flexibility and adaptability are essential skills for the Future of Work which employees can learn not just theoretically but through lived experience when they are on workation. Finally, for me personally, living as a Digital Nomad in different places in the world has helped me see our shared humanity. No matter how different people are, and no matter how annoying it is sometimes, I gradually learned to focus more on what unites, rather than what divides us. This helps me massively in my personal as well as in my professional life and is definitely a skill that I see becoming evermore important.

A Better Lifestyle for Less Money

The reality is that it’s possible to have a much more high quality lifestyle for significantly less money in places like Southeast Asia or Latin America compared to the cost of living that most Digital nomads and remote workers face in their home countries, which usually include Western nations like the US, Europe, Canada, Australia, or New Zealand. Many favourite remote work destinations, including Thailand, Indonesia, Costa Rica, or Mexico even started offering special visas for remote workers to boost their economies and bring talent into their countries. Personally, I am currently living on the Caribbean side of Mexico and I am sometimes seriously wondering how I am ever going to downgrade from the lifestyle that I am able to enjoy here. For now, I feel grateful and privileged to be able to live this way and conscious of soaking up every single moment of it.

Challenges of New Work Styles

Culture Shock & Leaving the Comfort Zone

Whilst exciting, being in a foreign country can be tough. Everything is different, and after the initial ‘culture shock’ that usually lasts around 2-3 weeks has passed, you usually need another 2-3 months to properly settle into your new life and get used to where things are and how things work. This cannot only be time-consuming but also draining when it comes to your energy.

Whilst you have all the exiting new (work)places to explore around you, it’s normal for humans as creatures of habit to long for some familiarity in the midst of the vast uncertainty that comes with living and working from a foreign country. It’s not uncommon to miss the smell of your home, the spontaneous catch-ups with your friends and family, the real life face-to-face interaction with colleagues, your favourite foods in the grocery store, and the general sense of psychological safety when walking out the door because we’ve walked the same street a million times before.

When we’re choosing to work remotely, we choose to leave our comfort zone and thereby catapult ourselves out of the convenient autopilot mode. And whilst it’s challenging, this is the space in which we can grow the most.


This is probably the most common and the most challenging issue that many Digital Nomads and people on workation face. Especially when you choose to travel alone, it requires active effort on your part to get to know new people. Based on my own and other people’s experience, finding your tribe gets more challenging the older you get, simply because many people become settled in their friendship circles as they age and it could be difficult for you to enter them as a newbie in a new country. However, there are certainly exceptions to that rule!

Moreover, co-working spaces, Facebook groups for expats, and meet-ups are a great starting point to find like-minded who face similar challenges. Sharing the burden makes it lighter for everyone! This does not only apply to sharing your feelings with new people, but with those closest to you, so make sure that you stay in touch with friends and family, as well as schedule regular catch-ups with your colleagues, for example for a quick virtual coffee or checking in.

On the employer side, it’s important to be aware of those feelings of isolation and disconnection that can be easily forgotten when thinking about things like workation since they are mostly associated with ‘living ones best life’. As much as people love to have freedom, they strive for connection. Being able to provide both will most likely lead to them to delivering the best results.

Time Zone Complications

Time zones can be another major challenge when it comes to remote working. Whilst regular meetings either have to be reschedules to an adequate time that works for all parties involved, many remote workers are left with no choice than to get up in the middle of the night to attend team or client calls. Whilst most people of I know who work like this say that this is the price they are willing to pay for the life they’re living in paradise, all of them agree that it’s very draining in the long run and negatively impacts their work performance.

Especially in the beginning when people move to a new location, face jet lag, and may additionally have to adjust to a very different climate than the one they are used to, this can wreck havoc with their biological rhythms and thus impact mental clarity. If employers are looking to offer longer workations and remote job opportunities, making a compromise that works for everyone will be essential.

Productivity Issues & Distractions

At first glance a workation is the perfect solution to allow employees to dip their toes into a bit of globetrotting without fully committing to remote work or becoming a Digital Nomad. Yet, offering workations might not be an approach that works for everyone. An employee with strong work ethic may approach a workation in the Bahamas very differently to someone else who is less than focussed – even when in the office.

Moreover, if you’re in a leadership position, you might wonder what happens if one of your team members is travelling to an ‘unknown’ place, gets to their hotel and there is no decent Wi-Fi for the important upcoming client meetings? What if their company laptop gets stolen? Or what will you do when you notice that there is lots of ‘cation’ and not so much ‘work’? Indeed, it’s tempting to go out and explore rather than convince yourself to stay home and do focussed work. Thus, new styles of working require great self-management and accountability on the part of the employee. Yet, initial trust from the managers side that the employee is going to execute the same level of output as they do in their normal working environment is equally important.

Additionally, I know from my own experience how triggering it can be when co-workers or clients think that you are “always on holidays”, simply because you’re living in a holiday destination. When we break away from the norm by choosing to live abroad and work online, that does not mean that we’re chilling all day. In fact, it requires a lot of self-discipline to actively stay away from all the temptations available in tourist destinations and do focussed work instead. So in a nutshell, remote working, workations, and being a Digital Nomad is not about being an irresponsible hippie – actually quite the opposite is required to make it work.

Take away: New Work styles are great – but they are not for everyone

I truly believe that companies can reap great benefits by introducing new work structures like workations and remote work as they can increase the motivation, inspiration, and overall wellbeing of employees. Nevertheless, it’s up to the team leaders to decide who may benefit from such more flexible ways of working whilst still delivering great outputs, and who might struggle with having too much freedom.

In this context, I remember my colleague Frank Widmayer saying to me once that he would always give someone more freedom in the beginning and then narrow it down if things don’t work out so well, rather than having someone earn their freedom over time. I really love that approach as it shows trust on the leaders side in the ability of their team members to lead themselves – an ability that becomes increasingly important in the Future of Work.

What do you think about workation and remote forms of working?
Do the pro’s or con’s overweigh for you – and why?

Mia Rosenzweig

Read more:

In search of a digital nomad: defining the phenomenon

This paper defines the rapidly emerging mobile lifestyle of digital nomads, who work while traveling and travel while working. Digital nomadism is driven by important societal changes, such as the ubiquity of mobility and technology in everyday lives and increasingly flexible and precarious employment. Despite the growing prevalence of this lifestyle, there is a lack of common understanding of and holistic perspective on the phenomenon. The emerging literature on digital nomadism is fragmented and scattered through different disciplines and perspectives. This paper looks into digital nomadism against the array of contemporary lifestyle-led mobilities and location independent work to develop a comprehensive perspective of the phenomenon. The paper also suggests a conceptual framing of digital nomadism within lifestyle mobilities. A limited number of empirical studies on digital nomads narrows the scope of analytical discussion in this paper. Thus, the paper defines aspects and directions for further conceptualization of the phenomenon.