Nomad Life Edition:

Roaming the World Building a Business​

The Pros and Cons of Being a Nomadic Entrepreneur​​

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Madison Coleman

Digital Marketing Associate | Travel Lifestyle Editor @ Insured Nomads

*This article was written by the Freaking Nomads team for the Insured Nomads audience.

Freaking Nomads was born in the perfect digital nomad style.

It was in the midst of hectically packing the bags for their upcoming trip to South East Asia that co-founders Luca and Irene launched their website and posted it on Instagram for the world to see.


It was also their first time exploring a new continent as digital nomads, which felt both exhilarating and nerve-wracking as they couldn’t turn to anyone in a similar situation for advice. For this reason, they decided to create a safe space for digital nomads around the world to feel part of a community that could empathize with them and offers meaningful support.


Little did they know that founding Freaking Nomads would not only help others live their best digital nomad life but also shape themselves into the nomadic entrepreneurs they are today.


Being two entrepreneurs on the go has been a wild ride and they’ve learned a lot about the unique challenges and benefits that come with running a business while constantly on the move in these first few months.


In this article, Freaking Nomads, in collaboration with Insured Nomads, will share their experiences building and growing their company while explore the benefits and challenges of being a nomadic entrepreneur.


Ready? Let’s go!

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What is a Nomadic Entrepreneur?

Before we start, you might probably ask: “What’s a nomadic entrepreneur?”


A nomadic entrepreneur is an individual who runs their business while constantly moving from one location to another. This type of entrepreneur is not tied to a specific physical location or office and instead relies on technology to conduct business from anywhere in the world.


Nomadic entrepreneurs often travel for extended periods of time, frequently changing their location every few weeks or months. They may work from coworking spaces, coffee shops, or even from their accommodations.


Many nomadic entrepreneurs are able to operate their businesses remotely by leveraging technology such as video conferencing, cloud storage, and collaboration tools. This allows them to maintain close contact with their clients and colleagues, regardless of their physical location.

5 of the Biggest Challenges and How to Overcome Them

Like all things in life, there are cons to becoming a nomadic entrepreneur.


But don’t worry! In my personal list of cons, I’ve included actionable advice on how to overcome the unique challenges that come with being an entrepreneur on the go. Let’s have a look at them one by one.

1. Maintaining Work-Life Balance

One of the biggest challenges of being a nomadic entrepreneur is finding a healthy balance between work and personal life.


When you’re constantly traveling and working remotely, it can be difficult to switch off from work mode and enjoy your free time, something which can easily lead to burnout.


Establish a daily routine that incorporates time for work, exercise, and leisure activities which can help maintain a good work-life balance.

2. Dealing with Isolation and Loneliness

Being a nomadic entrepreneur can be a lonely lifestyle. Even if you’re constantly surrounded by people, it’s easy to feel disconnected from others when you’re constantly moving and working.


You may also find it difficult to maintain relationships with friends and family back home, as you may not be able to see them as often as you would like.


Join online communities or attend events specifically for digital nomads can help alleviate feelings of isolation and connect you with like-minded individuals.

3. Finding Reliable Internet and Workspace

One of the most essential things for a digital nomad is access to reliable internet and workspace.


However, this can be a challenge in some areas, especially when you’re traveling to unfamiliar locations or countries where connectivity is spotty.


Do your research ahead of time and invest in quality equipment and technology that can help ensure you’re able to work efficiently, no matter where you are.

4. Managing Finances and Taxes

Another major challenge of being a nomadic entrepreneur is managing your finances and taxes.


You may need to keep track of expenses in multiple currencies and navigate different tax laws in each country you visit.


This can be time-consuming and stressful and can require a lot of attention to detail to ensure that you’re complying with all relevant regulations.


Work with a professional accountant or tax advisor who is familiar with the requirements for digital nomads and can help ensure you stay on top of your finances and avoid any legal issues.

5. Staying Motivated and Productive

Staying motivated and productive as a nomadic entrepreneur can be a challenge, especially when you’re working in a constantly-changing environment.


It can be difficult to stay focused and avoid distractions when you’re constantly surrounded by new sights and experiences.


Being a nomadic entrepreneur can be mentally exhausting, as you’re constantly dealing with new challenges and unfamiliar environments. This can lead to burnout and a lack of motivation over time.


Setting clear goals and deadlines, creating a dedicated workspace, and using productivity tools can help you stay on track. It’s also important to take breaks and prioritize self-care to avoid burnout and maintain your energy and motivation over the long term.

5 Benefits of Building Your Business While Roaming the World

The definition of a nomadic entrepreneur sounds pretty dreamy and there are indeed a lot of pros to becoming an entrepreneur on the go.

Let’s go through my personal list of pros I experienced building and growing Freaking Nomads.

1. Flexibility and freedom to work from anywhere:

One of the best things about being a nomadic entrepreneur is that you can work from pretty much anywhere with an internet connection.


That means you can work around your personal schedule and travel to your heart’s content, without having to worry about taking time off from work.


You can create your own working environment that suits your individual needs, whether it’s in a cute little cafe or on a beautiful beach.


As co-founders of Freaking Nomads, this type of flexibility has significantly increased our productivity and has allowed us to explore many places, hugely benefitting the community in need of first-hand advice on destinations for digital nomads.

2. Opportunity to explore new places and cultures

Being a nomadic entrepreneur gives you the chance to travel to new and exciting destinations and immerse yourself in different cultures.

You’ll get to experience things that you wouldn’t be able to if you were stuck in an office all day, every day.


Digital nomad entrepreneurs can take advantage of long-term travel opportunities and really get to know the local culture and customs.

Being able to travel full-time has thought us to be mindful of cultural differences and helps us learn how to effectively segment and cater to a global customer base.

3. Increased creativity and inspiration

Being in new and inspiring environments can spark your creativity and inspire you to come up with new ideas and approaches to solving problems.


Exposure to different cultures, people, and experiences can broaden your horizons and help you generate fresh ideas.


I started my digital nomad journey as a UX Designer and today, as a co-founder, problem-solving is at the base of every I do. Finding innovative solutions for our business has been crucially driven by traveling and meeting brilliant people while on the go, which is the next point on this list!

4. Ability to build a global network

Being a nomad entrepreneur allows you to build a network of contacts and colleagues from all over the world. You can make friends and connections that you wouldn’t be able to if you were working in one place all the time.


Building a global network can open up opportunities for new clients, business partners, and collaborations.


This is probably what I love more about nomadic entrepreneurship. Freaking Nomads is first and foremost a community and being able to meet like-minded people around the world has been the most rewarding aspect of being a nomadic entrepreneur.

5. Potential Cost Savings

Being a nomadic entrepreneur can be more cost-effective than having a traditional office job. By not being tied down to one location, you can save on rent or mortgage payments, utility bills, and transportation costs.


You may also be able to take advantage of lower cost-of-living areas, which means you can stretch your budget further and enjoy a higher quality of life.


At Freaking Nomads we strongly believe in remote working and that’s why we want to have a digital-first company. Having access to global talent and cutting down what for us are unnecessary costs has been a blessing and is still one of our core values.

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We’ve seen the benefits of the nomadic lifestyle for entrepreneurship, such as flexibility, the opportunity to travel, and increased creativity and inspiration, along with the potential to build a global network and cost savings.


However, the challenges of maintaining a work-life balance, dealing with isolation and loneliness, finding reliable internet and workspace, and managing finances and taxes, are also a reality for entrepreneurs on the go.


Nonetheless, actions can be taken to overcome these challenges, including establishing a daily routine, joining online communities, researching ahead of time, and seeking professional advice.


I encourage aspiring nomadic entrepreneurs like me to weigh the pros and cons carefully and consider whether a digital nomad lifestyle could be right for them and their business goals. And if you will choose to embark on this awesome journey, make sure to enjoy the ride!


Insured Nomads is the preeminent insurtech and traveltech platform empowering remote workers, expats, location independent and adventure travelers to safely & intelligently live, work and play anywhere around the world. An unprecedented combination of insurance and technology providing protection beyond benefits for those beyond borders.

Picture of Irene Lidia Wang
Irene Lidia Wang

Irene Lidia was born in Italy to parents of mixed Chinese-Italian heritage. She always felt like she didn't quite belong because of her diverse background, never fully accepted by either culture. In search of finding her own path, she moves to London for university but still struggles with feelings of not fitting in. She realizes her issues go deeper than location; it's an internal struggle. Irene's life takes a turn when she becomes a digital nomad, working remotely as a freelance UX Designer while traveling the world. This new lifestyle grants her a sense of belonging and freedom she had never experienced before. This inspired her to create Freaking Nomads, a safe and inclusive space in which everyone doesn't need to belong to any place or culture to feel at home.

Picture of Luca Mussari
Luca Mussari

Luca was born in a small town in Southern Italy but left for London in his early 20s, like many Italians, to seek better opportunities. After working as a waiter in a Japanese restaurant, he improved his English and continued his university studies. He climbed the corporate ladder and worked as a manager for global media agencies and British multinational companies. However, the Covid-19 pandemic caused him to re-evaluate his priorities after experiencing panic attacks. As a result, he became a freelance SEO consultant and a digital nomad, allowing him to work and travel simultaneously. He founded Freaking Nomads to inspire people to pursue unconventional paths and seek happiness wherever they desire.