So you want to become a Digital Nomad? with Lowell Sheppard

So you want to become a Digital Nomad?

By Guest Contributor Lowell Sheppard
Author of Dare to Dream, Lowell Sheppard, shares his ten tips for transition into the world of digital nomadism.

We find ourselves at a unique juncture in history. A time when0 the shackles of the 9-5 office job are gradually giving way to a life of unparalleled freedom. The concept of being a digital nomad has gained traction, and more individuals are embracing this transformative way of living. As digital nomads, we have the freedom to move as we please, all while creating and sustaining revenue streams that not only ensure our survival but maximize our life’s potential.

The realm of digital nomadism is diverse, encompassing a wide range of professionals from content creators and retailers to inventors, code writers, consultants, coaches, and manufacturers, just to name a few. The possibilities are limitless.

Four years ago, I embarked on this journey myself. After retiring from my role as the founder and leader of an NGO, I set sail on a new adventure with virtually no capital to my name. My sailboat became my home, my studio, my office, and my life laboratory. In addition to creating content for my small YouTube channel and writing, I co-run a film company with my son, who is a talented film director. I also hold the position of founder and CEO in a startup venture made possible by generous investors. It’s a dream come true.

Throughout my travels, both in the physical world and the digital realm, I’ve had the privilege of forging friendships with fellow digital nomads and have gathered valuable insights. Our community is incredibly diverse, comprising individuals of various ages, genders, nationalities, and lifestyles, including singles, couples, and groups. Some are minimalists, while others revel in high consumption. However, what unites us all is the discovery of a life that revolves around mobility and freedom. It’s about more than just remote working; it’s about dropping anchor wherever our hearts desire, making every day an adventure.

If you’re considering the transition into the world of digital nomadism or are just starting out on this thrilling journey, here are some tips I’ve gathered along the way. These insights will help you kickstart your journey, navigate the unique challenges, and establish a productive daily and weekly rhythm to optimize your digital nomad experience.

Tips for Aspiring Digital Nomads

#1.  Define Your Path: Determine your digital nomad niche or profession. What skills or interests can you leverage to create a sustainable income while on the move?

#2.  Consider your consumption: Be sure to have a clear idea of the lifestyle you want to live and figure out your cash flow.  For example, are you predisposed to a minimalist lifestyle or do you enjoy extravagance?  If the latter, be sure to have a financial cushion (read savings), As a Minimalist, I know many who set sail or went on the road with nothing and they live with few material possessions and are exceedingly happy.

#3. Create an Online Presence: Establish a strong online presence to showcase your skills, services, or products. This includes a professional website, social media profiles, and a well-crafted portfolio.

#4. Network Actively:  Join digital nomad forums, social groups, and communities to connect with like-minded individuals. The advice and support of fellow nomads can be invaluable.

#5.  Have portable lightweight tools:  Invest in the right tools and equipment that are essential for your work. This could include a reliable laptop, a high-quality camera, or other job-specific equipment.

#6 Daily and weekly Cadence.  Develop a structured daily and weekly routine that allows you to manage your work effectively. Prioritize tasks and find harmony between all aspects of your life.  It is not a matter of finding balance but a harmonious synergy.  Not every day is the same and not every hour is the same length.

#7. Be legally informed.: Familiarize yourself with visa requirements and legal regulations for each country you plan to visit. Ensure that your work and stay are compliant with local laws.

#8. Health Insurance: This is critical: Obtain appropriate health insurance and consider your healthcare needs while travelling. Regular check-ups and vaccinations are crucial. I recently, unexpectedly spent two weeks in a hospital on a remote island. Despite my language deficiencies, when I walked in I made sure I was holding my Government Issued Health Card to send the signal before I even opened my mouth that I was part of the system, and thus alleviating any stress or worry that I was an anomaly.

#9 Remember Cash is King; Budgets and Balance sheets should be created and referred to. But most important always consider cash flow both current and projected for the next 3-6 months. Maintain detailed financial records to track your income and expenses and be mindful of currency exchange rates. Forex can BITE you.

#10.  Adapt and Learn: Embrace adaptability as a core skill. Learn from your experiences and be open to change and growth. Every challenge is an opportunity for personal and professional development.

By adhering to these tips and embracing the lifestyle with an open heart and mind, you can unlock the true potential of being a digital nomad. It’s a journey that offers unparalleled freedom and adventure, and it’s a way of life that continues to evolve, shaping the future of work and living.


Lowell Sheppard is a seasoned adventurer, author, YouTuber and most recently the host for a new TV series on History Channel called Dare to Dream(to be released in 2024). He is also the founder of the Never Too Late Academy, which seeks to “help people everywhere acquire the courage and the tools to realize high stake dreams.” He currently lives in Japan on his boat. 


Suggested Reading

Based on Lowell’s own experience, this book provides important insights on to how to redesign your life, awaken dormant dreams, create audacious goals, and take high-stake risks to achieve them. It examines the anatomy of a dream and shares a four-step (DARE) program to realize high-stake dreams. Lowell has learned from both success and failure, but most of all, he has learned the benefits of pure grit and tenacity. This book will not only inspire the reader to have the courage to reach for the sky but also equip them with the tools to navigate into a better future. 

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