The Benefits and Challenges of a Remote Worker: Q&A with the SafetyWing Team

Being a remote worker is a freeing and fulfilling way to earn a living.

However, sometimes, it also presents some serious challenges that leave many remote-based workers feeling drained and unmotivated.

A few months back, we had the chance to be introduced to the team behind SafetyWing, the world’s first and only digital nomad and remote worker insurance plan. We quickly realized they had built one of the missing pieces of the future of work, and we were eager to learn more.

As you can probably predict, SatefyWing was created by digital nomads, a fully distributed team whose mission is to help other remote workers stay safe while traveling the world. They took a few minutes of their time to help us understand how they work as a remote team.

Sondre Rasch, Co-Founder & CEO

San Francisco, USA

Q: What drew you to the remote-working/entrepreneurial lifestyle?

A: When I was a teenager, I started a web hosting company with two friends I met through an online gaming community — one Dutch and one Romanian. For me, in a sense, being an online entrepreneur and working remotely was the norm, and a regular full-time job in a local company was the exception. I think working remotely is better because it gives you a lot more freedom in choosing how, where, and when to work. There is some adjustment when you are first getting started, but after a while, it means higher productivity and a higher quality of life. I also think it is a good thing for the world that people from all kinds of different countries can work together, and that opportunity becomes more available for people who are stuck in difficult locations or life situations.

Q: What is the biggest challenge you face working remotely?

A: Making sure relationships between employees are strong is a challenge. One solution to this is to work synchronously, but this is difficult to keep going when you work across different time zones (the second biggest challenge). In SafetyWing, we have implemented several things to try and remedy this, like quarterly team in-person gatherings and having a “virtual lunch” with no agenda.

Q: What is one thing you’re excited about seeing as the remote-working landscape develops?

A: I am very hopeful that the infrastructure and norms for working remotely keep developing. RIght now, you have to figure out a lot on your own, like how to get paid and how to get benefits. Soon, companies like Deel and SafetyWing will make that all a lot easier. I also look forward to the day where great remote-working practices are well-known throughout the community. This way, each startup working with a distributed team doesn’t have to try and fail as much as many current distributed startups do.

Enelin Paas, Head of Partnerships

Nomad

Q: What drew you to the remote-working/entrepreneurial lifestyle?

A: I am simply not able to sit in a closed cubicle! I have always loved traveling a lot, and the cold weather in Estonia made me curious about finding more possibilities out there in the world.

Q: What is the biggest challenge you face working remotely?

A: Making sure that people understand you via call and/or video, and you understand others correctly. Communication is harder and more detailed via the internet because it’s harder to understand people without any body language — in both voice and video calls. Don’t get me wrong, it ends up working, but it’s usually not that easy with some complicated topics or frantic teamwork brainstorming sessions. The things like quarterly team meetings in person help solve that!

Q: What is one thing you’re excited about seeing as the remote-working landscape develops?

A: I love to see how working online is not that “wow” anymore, and even though it’s still new, it’s getting accepted as a normal thing. More nomads, more remote companies, and a lot of great services are supporting this lifestyle. It’s exciting being immersed in the future of work transformation and seeing the change that is happening now at this very moment.

Eric Michelson, Content Creator

Buenos Aires, Argentina

Q: What drew you to the remote-working/entrepreneurial lifestyle?

A: I was sick of “traditional” jobs where I needed to report to the same place every day and be constantly surrounded by the same kinds of experiences. I realized that the internet offered a lot of potential ways to overcome these struggles. Having the ability to work wherever and whenever I want, allows me the freedom for exploration that I never got in fixed-position jobs.

Q: What is the biggest challenge you face working remotely?

A: Learning how to balance work and play is definitely hard. Before, I’d go to a job, come home, and repeat. Weekends were “play time.” Problem solved. Now, I’m perpetually on a working holiday, and many of the people I meet are travelers. But they’re not working; they’re just on holiday. So they’re always playing. I can’t just go and hike a mountain for five days… I need to work.

Q: What is one thing you’re excited about seeing as the remote-working landscape develops?

A: I think as the internet matures, there are going to be a lot more opportunities for people to experience a level of occupational freedom that they didn’t even know was possible. I think that’s going to usher in an age of smarter work as opposed to the “quantity over quality” mindset that previous generations have been using as their typical work model. Worker satisfaction is now recognized as a crucial factor in employment, and it’ll be exciting to see how the internet helps play a role in maintaining a positive workplace environment.

Francisco Ortiz, Partnerships Consultant

Nomad

Q: What drew you to the remote-working/entrepreneurial lifestyle?

A: I’ve always loved traveling, and I’ve been obsessed with freedom since I was very little. I’ve tried everything — from small family businesses to startups to MNCs to corporate America. Being able to work online gives me the freedom to find arbitrage opportunities by making a well-developed country income while traveling to affordable countries and investing in multiple different markets. The possibilities are endless, and my freedom grows more and more every year.

Q: What is the biggest challenge you face working remotely?

A: Having the discipline to keep growing. Arbitraging makes it very easy to have a good and comfortable life, and since no one is behind me telling me what to do or where to go, I need to keep myself focused and motivated to keep moving forward.

Q: What is one thing you’re excited about seeing as the remote-working landscape develops?

A: The internet is the closest thing to a free market there is, and I see more and more people from developing countries having access to opportunities that will make them independent from their possibly corrupt governments, thus giving them access to a lot more freedom. I see an increase in competition for job opportunities that will make everything fairer by leveling the playfield. That will generate a need for a more results-based approach to managing workers: no more gatekeepers or privileged positions. If you’re good at your craft, you’ll be ok. If you’re not, you’ll have a hard time in this “new open world.” Everything will be more transparent and fair.

Barbara Jovanovic, Social Media & Content Manager

Nomad

Q: What drew you to the remote-working/entrepreneurial lifestyle?

A: As someone who studied art, I never felt like I had to accept the concept of what society deemed to be an appropriate workplace or acceptable working hours. My schedule is mostly tailored to whenever I feel most productive or creative, regardless of the time of day (or night… we’ve all been there). The lack of opportunities for work in my home country made me discover that working online eliminates borders and offers an entire world of opportunities.

Q: What is the biggest challenge you face working remotely?

A: Finding ways for my professional and personal life to coexist peacefully. One of the biggest lessons for me was learning how to truly work while I travel — no matter how exciting the destination is, I have to keep in mind I’m not there just as a tourist. Work comes before sightseeing and adventures, but that is what’s great about working remotely — it has the potential to accommodate your need to explore. Another challenge is learning how to be a productive member of a remote team and overcoming communication hurdles with people living in different time zones. Even though it does take some time to adjust, it is incredibly inspiring to have the opportunity to meet and collaborate with people from all over the world.

Q: What is one thing you’re excited about seeing as the remote-working landscape develops?

A: I am hopeful that more companies will realize the benefits of remote work, especially when it comes to hiring new people — instead of being restricted to a local talent pool, they can find people with the rights skills anywhere in the world. I’m also interested to see how the ability of nomads to simply choose a country with different standards of living and all the amenities they need will fundamentally change the governments of the world.

SafetyWing is itself a distributed startup working with freelancers and entrepreneurs all over the world. Being a company made up of remote workers with a single focus on helping evolve the distrusted landscape, this is one team that’s chock-full of knowledge about what it’s like being both employers and employees in an entirely online environment.

As the world of work changes rapidly, we’re proud to call SafetyWing our trusted partner. They are at the forefront of the digital revolution and genuinely care about making sure all freelancers, remote workers, and digital nomads have the protections they need to stay healthy and secure. While Deel focuses on making every party compliant and safe from a legal standpoint, being insured is one of the simplest ways of staying safe at a human level, and we’re positive that there’s no better company out there who knows how to keep internet employees safe.

With so much care and attention paid to the online, remote-working space, we’ll soon see a lot more improvements and advancements that will overcome some of the most common problems and hurdles. And as each day brings more and more innovation, there’s no doubt in anyone’s mind that it’s an inspiring time to be an online worker!