Pros and Cons of Being a Digital Nomad

The Best and Worst of the Digital Nomad Lifestyle

Welcome to this week's issue, where we're exploring the pros and cons of the digital nomad lifestyle. In recent years, this lifestyle has become increasingly popular, but it's not for everyone. Here are some key points to consider before making the leap:


  • Flexibility and freedom to live and work from anywhere: One of the biggest perks of being a digital nomad is having the freedom to choose where you live and work. You can work from a beach in the Bahamas, a mountain town in Colorado (like I did), or anywhere else in the world. This level of flexibility also allows for a better work-life balance, as you can choose to live in a place with a lower cost of living or more aligned with what you love to do.

  • Opportunity to travel and experience new cultures: As a digital nomad, you're not tied to one location, so you can (and should) explore different parts of the world and immerse yourself in different cultures. You can use to find some of the best locations for digital nomads!

  • Potential for increased income and career growth: Digital nomads have the ability to take on freelance projects or side hustles in addition to their full-time remote job, which can lead to an increase in income. Because digital nomads can choose to work on projects that align with their skills and interests, they may experience faster career growth and greater job satisfaction. Many digital nomads also report having more control over their income, as they are not tied to a specific location or employer. This makes it easier to negotiate rates, increase earning potential, and build a diverse portfolio of clients and projects.

  • Ability to create a work-life balance that works for you: As a digital nomad, you have the flexibility to set your own schedule and work from anywhere. This allows you to prioritize your work and personal life in a way that works best for you, whether that means taking a mid-day break to explore a new city or dedicating certain hours of the day (or night) solely to work. By having control over your schedule, digital nomads often report increased productivity and job satisfaction, leading to a happier and more fulfilling lifestyle.

  • Chance to build a global network of like-minded individuals: As a digital nomad, you'll have the opportunity to connect with a diverse community who share your passion for location independence. This can lead to networking opportunities, potential collaborations on projects, and the formation of long-lasting friendships. Many digital nomads also join online communities, attend meetups and conferences, and even organize their own events to connect with other nomads. Maybe we'll even host one of our own someday!


  • Difficulty in maintaining relationships with friends and family: As a digital nomad, It can sometimes be a challenge to maintain relationships with loved ones and friends while traveling around the globe. The constant change of location and distance can make it hard to keep in touch, and the uncertainty of the lifestyle can cause strain on relationships. Dating can also be a challenge if you’re constantly on the move. This struggle to maintain relationships can cause you to slow down or pause this lifestyle for a while. Because while traveling to exotic places is cool, it’s no substitute for your family and relationships.

  • Difficulty in finding stable housing and healthcare: As a digital nomad, finding stable housing and healthcare can be a challenge. You may have to constantly search for short-term rentals or rely on accommodations like Airbnb or hostels, making it hard to settle down and establish a sense of home (or just not living out of a suitcase). Additionally, finding healthcare providers in every location you travel to can be difficult and may require a bit of extra (and possibly annoying) research and planning.

  • Financial instability and lack of job security: One of the main concerns for digital nomads is the lack of stability and security in our income. Without a traditional 9-5 job and benefits, digital nomads often have to rely on freelance or project-based work. This can make it difficult to predict and plan for future expenses, as work and income may be inconsistent. Additionally, digital nomads may not have access to traditional benefits such as health insurance, 401k or retirement savings plans, which can make it harder to save for the future and plan for unexpected expenses.

  • Lack of community and belonging: The nomadic lifestyle can often be isolating and make it difficult to form strong connections with others. The constant change of locations and lack of a permanent home can make it challenging to build a sense of community and belonging. It can be hard to find like-minded individuals who understand and share your lifestyle. Without a sense of community, it can be hard to find a sense of belonging or to find people to share your experiences with. This can lead to feelings of loneliness, disconnection and can even impact your mental health. This can be a significant barrier to overcome, especially for those who are used to having a strong support system in their life.

Being a digital nomad can be an incredible experience full of adventure and opportunity, but it also comes with its own set of challenges. It's important to weigh the pros and cons and make sure that the nomadic lifestyle is right for you before taking the leap. But for those who are ready for the adventure, the rewards can be great.

A final word of advice from an unknown digital nomad:“If you don’t like it… how hard would it be to move back home or get an apartment?”

Thanks for reading our latest issue of The Jailbreak! If you're considering taking the leap or have any questions, feel free to reach out to me at @JackCalvinRoss on Twitter. Don't forget to sign up for our newsletter for weekly tips on becoming location-independent and creating digital leverage!