Work, Wander, and Well-being: Mastering the Art of the Working Holiday

Taking your business on the road for a working holiday presents an enticing blend of work and leisure, allowing you to explore new destinations while keeping your operations running smoothly.


This concept has gained popularity with the rise of digital nomadism and the increased flexibility in work arrangements. To ensure success, it’s crucial to approach this venture with strategic planning and thoughtful consideration of various factors.


Here are the key strategies and considerations to ponder:


  1. Technology and Connectivity
  • Reliable Internet Access: Your foremost priority should be ensuring consistent and reliable internet access. Research connectivity options in your intended destinations, including local SIM cards with data plans, satellite internet, portable Wi-Fi devices, and co-working spaces known for their high-speed internet.
  • Tech Tools and Software: Leverage cloud-based services for data storage and collaboration, ensuring you can access your work from anywhere. Utilize task management and communication tools to stay connected with your team or clients.
  1. Time Management
  • Flexible Scheduling: Adopt a flexible yet disciplined approach to your work schedule. Be mindful of time zone differences that may affect your communication with clients or your home office. Allocate specific hours for work and exploration, ensuring neither aspect is neglected.
  • Productivity Techniques: Employ productivity methods such as the Pomodoro Technique or time blocking to maximize your efficiency during work hours, allowing you to fully enjoy your leisure time.
  1. Legal and Financial Considerations
  • Insurance and Health Care: Ensure you have comprehensive travel and health insurance that covers you internationally. Consider any vaccinations or health checks you may need before departure.
  • Tax Obligations and Business Regulations: Understand the tax implications and any local business regulations that may apply to working in a foreign country. Consult with a tax advisor or legal professional to navigate these complexities.
  1. Work-Life Balance
  • Setting Boundaries: It’s crucial to establish clear boundaries between work and leisure time. Be disciplined about “switching off” from work to immerse yourself in the new environments and experiences.
  • Mindfulness and Well-being: Regularly practice mindfulness and self-care routines to maintain your physical and mental well-being. This balance is key to sustaining productivity and enjoying your working holiday to the fullest.
  1. Networking and Community Engagement
  • Local Networking Opportunities: Look for opportunities to meet local professionals and other digital nomads. Co-working spaces often host networking events and workshops that can enrich your experience and provide valuable connections.
  • Online Communities: Join online forums or groups for digital nomads to share tips, advice, and experiences. These communities can be invaluable for support and networking.
  1. Adaptability and Contingency Planning
  • Flexibility: Be prepared to adapt your plans as needed. Travel uncertainties, work demands, and personal preferences may change during your trip.
  • Emergency Plan: Have a contingency plan for emergencies, including knowledge of local emergency services, access to emergency funds, and backup accommodation options.
  1. Cultural Sensitivity and Local Experiences
  • Cultural Awareness: Take the time to learn about and respect the local customs and cultural norms of your destinations. This mindfulness ensures harmonious interactions and enriches your travel experience.
  • Explore and Engage: Allocate time to explore local attractions, cuisine, and culture. Engaging with the local community and environment can inspire creativity and provide a refreshing perspective on your work.



Transforming your working holiday into a productive and fulfilling experience requires careful planning, flexibility, and a balanced approach to work and leisure. By considering the key strategies outlined above, you can navigate the challenges and reap the rewards of combining work with the adventure of travel. This not only fosters personal growth and resilience but also opens up new opportunities and insights for your business.


If this article has inspired you to think about your own unique situation and, more importantly, what you and your family are going through right now, please contact your advice professional.

This information does not take into account the objectives, financial situation or needs of any person. Before making a decision, you should consider whether it is appropriate in light of your particular objectives, financial situation or needs.

(Feedsy Exclusive)


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