How Our Family Conquered Working Remote While Traveling the World (Without Losing Our Minds)

Five years ago, I never imagined I’d be running a business and working remote while traveling the world with my family.

Our first attempt at digital nomad life in Bali was a hilarious disaster. We only had WiFi on our porch, forcing us to work in our landlord’s bustling restaurant, where video calls were drowned out by sizzling woks and lively chatter.

Those two weeks taught us invaluable lessons about flexibility and patience. Today, as many as 48% of digital nomads travel with kids under 18, proving that working remote while traveling is more than a trend—it’s a lifestyle.

While our initial experience was far from perfect, it laid the groundwork for a seamless family adventure on the go. Here are the strategies we’ve developed to balance remote work, travel, and family life.

The Reality of Nomadic Family Life

Let’s be real – no sane digital nomad actually works from the beach. Sand and electronics are a disaster waiting to happen.

The truth about nomadic family life is both more challenging and more rewarding than most people imagine.

Myth vs. Reality

Myth: Every day is an exotic adventure.

Reality: We still have daily mundane chores – grocery shopping, laundry, and household management – just in a new city or country every month or so.

The Challenges

• Constant adaptation: New environments, time zones, and cultures keep us on our toes.
• Time zone juggling: Coordinating and setting meeting times across multiple time zones becomes a complex puzzle.
• Work-life balance: It’s easy to blur the lines when your office is everywhere.
• Education on the go: Ensuring our kids don’t fall behind while embracing worldschooling.
• Technology limitations: Finding reliable internet and appropriate workspaces in different locations.

The Incredible Rewards

• Global perspective: Our kids are growing up as true citizens of the world.
• Family bonding: Shared adventures create unbreakable bonds.
• Flexibility: We can chase summer year-round or follow our curiosity wherever it leads.
• Cultural immersion: We’re not just visiting places; we’re living in them.
• Personal growth: Constant challenges build resilience and adaptability for the entire family.

David and I both had client calls throughout our cruise across the Pacific. Cruising from Seattle to Sydney sounds glamorous until you’re desperately searching for a quiet spot.

Every lounge had background music or live performers, making professional communication a challenge.

Thank goodness for noise-cancelling headphones – our saving grace in maintaining a professional image while literally sailing between continents.

Nomadic family life isn’t for everyone, but for those willing to embrace the unpredictability, it offers a richness of experience that’s hard to match in a traditional setting.

Kid Management Masterclass

Managing work while keeping our son, Little Man, engaged can be one of the biggest challenges of nomadic family life.

Here are some effective strategies we’ve developed:

Engaging Little Man During Work Hours

To keep him occupied, we mix up structured activities and free play, which is mostly online gaming with friends around the world now that he’s older.

We encourage him to explore local attractions, join workshops, or participate in cultural events. This not only keeps him entertained but also enriches his travel experience.

Educational Travel Opportunities

We embrace worldschooling by integrating educational experiences into our travels. Museums, historical sites, and nature excursions become our classroom, allowing Little Man to learn in real-world contexts.

Balancing Work and Family Time

We establish clear boundaries between work and family time. Mornings are often dedicated to focused work, while afternoons are reserved for family activities.

This structure helps everyone know when it’s time to be productive and when it’s time to play.

Homeschooling/Worldschooling Integration

For our homeschooling approach, we integrate worldschooling by tailoring lessons around our experiences.

Plus, we host a podcast that interviews other worldschooling families, sharing insights and inspiration for our journey.

Pro Tip: Involve the Kids

Involve your kids in planning your itinerary. We let Little Man choose activities or destinations, like picking our waterfall hikes in Costa Rica, which fosters excitement and gives him a sense of ownership over our travel experience.

Practical Logistics

Navigating the practicalities of family travel can be daunting, but with careful planning, it becomes manageable. Here are key logistics to consider:

Choosing Family-Friendly Destinations

When selecting where to go, we prioritize family-friendly destinations that offer a mix of activities for both adults and kids.

Look for places with accessible attractions, safe environments, and amenities like parks, museums, and child-friendly restaurants.

Internet Reliability Considerations

Reliable internet is crucial for working remote while traveling. Before booking accommodations, we check reviews specifically mentioning WiFi quality.

For vacation rentals, we often message the owners before booking to ask for speed test results before booking.

Budget Management

Traveling as a family requires careful budgeting. We track our expenses using apps like Mint or YNAB (You Need A Budget) to ensure we stay within our limits.

We also look for discounts on family activities and accommodations to stretch our budget further. And we’re not afraid to ask for family or kid discounts when buying tickets or booking accommodations.

Healthcare and Insurance Tips

Healthcare access varies by country, so we research local medical facilities before arriving.

Plus, we invest in comprehensive global health insurance that covers medical emergencies and trip cancellations, providing peace of mind while on the road.

We also elect travel insurance with SafetyWing for our spurts of fast travel adventure!

Pro Tip: Create a Packing List

Develop a packing list tailored to your family’s needs. Include essentials for work, travel gear for kiddos, and any educational materials. This helps streamline the packing process and ensures you don’t forget anything important.

Mental Health and Relationship Preservation

Maintaining mental health and nurturing relationships while traveling as a family can be challenging. Here are some strategies we’ve found effective:

Preventing Burnout

To avoid burnout, we prioritize self-care. This includes setting aside time for individual hobbies, exercise, and relaxation. Regular breaks during work hours help recharge our energy and focus.

Couple Communication Strategies

Open communication is essential. We make it a point to check in with each other regularly, discussing our feelings, challenges, and successes. Scheduling regular date nights, even in new locations, helps us maintain our connection.

Maintaining Work-Life Balance

Establishing a clear separation between work and family time is crucial. We set specific work hours and stick to them, ensuring that evenings and weekends are dedicated to family activities and downtime.

Embracing Flexibility

Travel can be unpredictable, so we embrace flexibility in our plans. Being adaptable allows us to navigate unexpected challenges without added stress.

Pro Tip: Create a Family Routine

Developing a family routine can provide structure amidst the chaos of travel. Simple rituals, like a weekly family meeting or game night, help strengthen our bond and create lasting memories.

Top Tips from the Trenches

After over five years of navigating the digital nomad lifestyle with our family, we’ve learned some valuable lessons. Here are our top pro tips for aspiring nomadic families:

1. Embrace the Chaos

Expect things to go wrong—flights may be delayed, WiFi may fail, and plans will change. Like the time we were house sitting in Mexico and the internet was so bad that it would go out anytime we got more rain than a bare sprinkle!

Embracing the chaos will help you stay calm and adaptable when challenges arise.

2. Stay Organized

Use digital tools to keep your life organized. Apps for budgeting, task management, and scheduling can streamline your daily routine and reduce stress. Keep it simple!

3. Build a Support Network

Connect with other nomadic families or expats in your destinations. Online communities and social media groups can provide support, advice, and friendship.

4. Be Culturally Curious

Encourage curiosity about the places you visit. Engage with locals, try new foods, and participate in cultural events to enrich your family’s travel experience.

5. Learn from Mistakes

Every misstep is an opportunity for growth. Like when we grossly underestimated tourism in coastal Australia, and almost couldn’t find a hotel room because everything in our budget was sold out.

Instead of panicking or getting mad, this is where it’s key to reflect on what went wrong and how you can improve for next time. This mindset will help you develop resilience as a family.

If it helps, remind yourself you want to model the behavior for your kids.

Inspirational Takeaway

Remember that the journey is just as important as the destination. Each experience—good or bad—contributes to your family’s unique story.

Like the time a dirt road collapsed under our 4Runner when we were driving through Ecuador on the Pan-American Highway. Celebrate the small victories along the way!

Final Thoughts

Balancing remote work, travel, and family life as digital nomads is both rewarding and challenging. Our journey has been filled with unexpected twists, but the experiences and memories we’ve created are invaluable.

As you consider this lifestyle, remember that preparation, flexibility, and open communication are essential.

Equip yourself with the right tools, involve your family in the journey, and embrace the chaos—it often leads to the most memorable moments, The world is waiting for you!