10 Challenges of Being a Digital Nomad [2023]

edited May 20 in Lifestyle

Imagine working from a beach in Bali one day and from a bustling café in Taipei the next. It's the digital nomad lifestyle — tales of beachside workstations and wanderlust-worthy Instagram feeds. Yet, beneath the sun-drenched snapshots lies a lifestyle fraught with challenges unseen in a regular 9-to-5 job. 

From unreliable internet connections to language barriers or even the crushing loneliness of a new city — these factors can morph the digital nomad dream into a harsh reality. Understanding these challenges gives you a clearer picture of the digital nomad lifestyle. Brace yourselves because we're about to demystify the remote work lifestyle. 

1) Employment 

Finding a job that lets you live anywhere is your first challenge. While many employers still prefer face-to-face interactions, certain professions, like editing or coding, value productivity and deadlines above your physical presence.

Being a digital nomad often means you're self-employed. You enjoy flexible hours and work conditions. But remember, being self-employed also means you need discipline to keep the income flowing. It's a constant hustle, always looking for the next gig or paycheck. This never-ending chase can be challenging at times.

Once you get your remote job, working out the logistics of living remotely into practice is probably the next challenge.

2) Finances/Taxes 

Receiving income shouldn't be an issue if you work for a company and have internet or card access to your bank account. However, if you're a teacher setting up courses before you arrive in a country, convincing students to pay fees to an offshore bank can be challenging.

The deal with taxes for digital nomads is complex as it depends on the country you're living in and your home country. Some countries determine tax residency by your nationality and how long you stay there. If you meet their criteria, you might have to pay taxes on all your income, no matter which country it comes from.

Other countries only tax the income you earn within their borders, which means that if you have entered the country on a holiday visa, you might have legal complications. But, if you're genuinely working remotely for clients or companies outside of that country, you won't likely pay taxes while you are there. 

As an American living abroad, no matter where you live, you must file a US federal tax return and pay US taxes on your worldwide income. Talk to a tax pro or get advice from tax authorities in both your home country and the country you're living in. They'll give you the lowdown on specific rules to ensure you do the right thing. 

3) Deciding where to live and work 

Your next challenge is deciding where in the world to go next. The world is filled with fascinating places, and picking just one can be tricky. Factors that might influence you include:

  1. Political climate: Is the country stable, or is there a risk of political unrest that might put you in danger? Check the US Department of State's Travel Advisories for current information. 
  2. Safety: How safe is the city or country? Think about personal safety, crime, cyber security, and healthcare quality. 
  3. Cultural factors: What cultural norms or rules should you be aware of? Are there certain clothing items you should avoid? Is the food suitable for your diet? Are any areas off-limits for tourists? 
  4. Visa requirements: How long can you stay in the country with your visa? If you love the place, will you need to exit and re-enter to extend your stay (a visa run)? 
  5. Currency exchange: How much local currency can you get for 100 US dollars? How does this relate to your income and living costs in that country? 
  6. Leisure activities: What activities can you engage in during your free time? Consider options for socializing, hobbies, and sightseeing.

4) Language and cultural barriers 

Ever found yourself in a sticky situation, not knowing why that friendly chat left someone irked? It could be a language or cultural barrier you've stumbled upon.

As a seasoned digital nomad, you might have noticed that simple things like making eye contact mean different things in different cultures. In America, it shows you are interested in what's going on and likely to be trustworthy. Still, it is often considered disrespectful or overly aggressive in Japan or Korea.

To avoid such misunderstandings, watch the locals. See how they communicate through body language and speech. It's a helpful way to navigate human connections in a new place. 

Remember, as a digital nomad, you're not just a visitor but also your country's ambassador. Dress appropriately, respect local customs, and be mindful of local beliefs. If the local lifestyle doesn't gel with you, it might be time to pack your bags and seek your next adventure elsewhere.

5) Finding your way around a new city 

Navigating a new city is difficult, especially if you can't understand the local language or read the signs. It's a good idea to learn some basic phrases before you arrive; it helps with communication and understanding the local culture and people.

Working from home can get lonely, so finding your co-working space is the holy grail. You can meet new people, make friends, and learn from other remote workers. However, shared workspaces have their challenges. You might need a quieter place if someone is too loud or chatty while trying to work. Remember, find a balance that works for you.

6) Healthcare access 

Living as a digital nomad often means being drawn to places with lower living costs. Unfortunately, these areas sometimes have subpar housing, healthcare, and issues like air and noise pollution. The local tap water might not be drinkable, and eating restricted diets can contribute to poor health. Getting sick far from home can be challenging, with language barriers making it hard to seek medical help or find restrooms quickly.

Staying healthy becomes a top priority, especially when you're self-employed and only earn when you can work. Make sure:

  • Your vaccines are current 
  • Maintain a balanced diet 
  • Get enough sleep 
  • Engage in social activities

Before embarking on your journey, secure comprehensive travel and health insurance, and set aside some funds for emergencies. Being prepared is the first step towards navigating the healthcare challenges of being a digital nomad.

7) Not having a permanent home 

Living the digital nomad life means figuring out what to pack for your next adventure. It's a constant puzzle: do you pack light and purchase necessities along the way or bring everything you might need, saving your cash for other experiences? It's usually best to strike a balance and adjust when needed.

There are more challenges when you don't have a permanent home:

  • Wi-Fi connections: Your internet is your lifeline, so having to arrange it repeatedly can be a bit of a headache. 
  • Adaptor issues: Different countries have different plug shapes and voltage requirements, so you might need adaptors or converters. 
  • Frequent travel expenses: You'll need to factor these costs into your budget since hopping from place to place is part of the lifestyle. 
  • Dealing with official paperwork: Handling documents that need witnessing can be tough on the move. And don't even think about losing your passport!

Despite these challenges, the experiences you'll gain as a digital nomad are often well worth the occasional inconveniences.

8) Lack of social life and emotional support 

Frequently moving can make it tempting to avoid forming deep friendships. Often, connections made on the move are fleeting, not the kind to lean on when things get tough.

Relationships can be complicated enough when you're in the same place, let alone across different time zones. It isn't just about romantic partnerships but also friendships and family ties. Long-distance relationships require more work and can be more challenging to navigate.

Staying connected with loved ones requires effort, especially when meetups are few and far between. Yet, it's worth every bit of effort. The old saying rings true: "No man is an island." Carve out time for the people who matter most to you, as these connections significantly enhance your mental well-being.

9) Mental Health 

Burnout, loneliness, and stress can lead to mental health issues. Sometimes people think they can solve problems by making a new start, but if you don't address the core problem, a fresh start means less support from those who care. [Text Wrapping Break][Text Wrapping Break]Finding a therapist may be difficult with language barriers and frequent moves. Online apps like BetterHelp let you talk with your therapist to provide the support you need.

Working alone, far from familiar surroundings, can feel isolating. Continually moving means you often lack deep connections, which can harm your mental health. We're hardwired to crave community; our ancestors thrived in tight-knit groups, and positive interactions make us feel good. Some countries have alcohol in convenience stores available 24/7, plus easy access to prescription drugs can pose additional risks.

The good news is that there are many ways to forge warm connections. Hang out with family and friends – even online if they aren't around. Grab lunch with co-workers or initiate a friendly conversation with the person serving you coffee. Little interactions like these can go a long way in making you feel more connected to the world around you.

10) Finding time to have fun 

Many people think the digital nomad lifestyle is about exploring new places and having exciting adventures. While that's part of the appeal, it's not always the reality, especially when working. You might spend more time finding accommodation, hunting for groceries, buying clothes, or figuring out Wi-Fi than sightseeing or people-watching.

Work is crucial, but so is relaxation. If you don't take time to unwind, you'll find it harder to focus on your job. Being organized and following a routine can help balance work and leisure. Make sure to schedule regular breaks, whether daily, weekly, or yearly, so you can truly enjoy living in different parts of the world. Being a digital nomad is not just about working from exotic locations but also experiencing and enjoying them.

The digital nomad lifestyle offers an exceptional opportunity to merge work and travel. While it's not always possible to sidestep the challenges and mistakes that come with it, dealing with these issues can make the journey more enjoyable.

The beauty of this lifestyle lies in the unique blend of work, exploration, and the freedom to roam the world. By meeting these challenges head-on, you ensure that the journey is not just about surviving but thriving and living the digital nomad dream. 

Robert is a Taiwan-based writer and digital marketer at iamrobert design. He has a passion for helping people simplify their lives through tech.


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