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From Corporate HR to Digital Nomad Mom: How a Bookstore Find Changed My Life
A chance encounter with a book at a local bookstore turned me into a digital nomad mom! I bought a story about a family sailing around the world and realized there was so much more to life than the confines of my corporate office.
This spark ignited a nearly decade-long journey for my husband, David, and me as we explored ways to transition into long-term travel.
In June 2019, I took a bold step and left my stable career as an HR Director, a decision that felt both exhilarating and daunting.
Walking away from a secure job was one of the scariest moments of my life, but it turned out to be the best choice I could have made.
Now, as a digital nomad mom, I’ve embraced a life filled with adventure and discovery alongside my family, and I’m excited to share the lessons learned throughout this incredible journey.
The Spark for Change
On our first international trip as a family to the Virgin Islands, our son was just 7 months old. David took video calls from our condo, blending work and family time, which felt both exciting and liberating. It gave us the confidence to keep planning!
Our tipping point came in the summer of 2018 when I lost my job as the main provider for our family. By then, David had been the stay-at-home parent for our son for almost six years.
While I was unemployed, we relied on our short-term rental income and David’s online teaching. We realized that if we could make life work in Chicago, we could do it in more affordable countries.
So, we created a one-year plan to turn our vision into reality. With remote income and determination, we just needed time to declutter and complete our to-do list.
However, I also faced fears that loomed large during this transition. Beyond a fear of failure, I worried about whether we could sustain ourselves while traveling and how our son would adapt to a new educational environment.
Planning the Transition
To get ready for our big move to full-time travel, we first focused on our finances. We looked at how much money we were making from our short-term rental and David’s online teaching.
And, we created a budget to help us understand how much we could spend while living in cheaper countries. This planning showed us that if we could manage our lives in Chicago, we could thrive in other places too.
David had online teaching so I looked for remote work opportunities that would let me keep a flexible schedule while supporting our family.
Logistics were another big part of our preparations. From visa requirements and time zones to housesitting opportunities and repositioning cruises, we had so many exciting twists to our travels even before we left.
As we started to declutter and downsize our belongings, I felt both excited and nervous about leaving behind the comforts of home. To this day, I still miss my SodaStream and my InstantPot!
Embracing the Digital Nomad Lifestyle
Adapting to life on the road as a traveling family required flexibility and creativity. For work, I found freelance writing opportunities as well as travel blogging while David continued his online teaching.
Worldschooling became our approach to our son’s education. After a good few months of decschooling we started out with an unschooling approach, learning through our travels.
Overall, our unconventional method proved both challenging and rewarding, as we balanced structured learning with real-world experiences. One of our unexpected pleasures has been watching our son initate his own education!
One of our main challenges was maintaining a sense of routine and stability while constantly on the move.
To this day, it can still be a challenge but we overcame this by establishing flexible daily schedules and creating familiar rituals, regardless of our location. For example, we always have family reading time before bed.
On top of this, managing work commitments while exploring new places required careful planning and time management. It still does! We plan out work, family, and sightseeing time in advance so that we can fit everything in.
Lessons Learned Along the Way
My family’s journey has been transformative, teaching us far more than we ever anticipated. We’ve discovered that flexibility and adaptability are our greatest strengths.
Worldschooling our son has shown us that education extends far beyond traditional classroom walls. He’s learned geography, language, and cultural understanding through direct experiences that no textbook could replicate.
Traveling has fundamentally changed our perspective on work and life balance. My corporate HR background, with its structured environments and predictable routines, now seems like a distant memory.
While I occasionally miss the professional camaraderie and clear career progression of my previous roles, the freedom and personal growth we’ve experienced far outweigh those nostalgic moments.
The most profound lesson has been understanding that success isn’t defined by a job title or a corporate ladder, but by the richness of experiences and the strength of our family bond.
We’ve navigated challenges together, from managing remote work to adapting to new cultures, which has made us more resilient and connected.
Our son is growing up with a global perspective, understanding that the world is vast, diverse, and full of opportunities—a lesson that no traditional education could provide as authentically as our travels have.
Struggling to plan your travel adventures?
As a former HR Director and full-time worldschooling mom since 2019, I’ve got answers. You don’t need to do this alone.
Advice for Others Considering a Similar Path
Transitioning from a corporate career to a location-independent lifestyle isn’t just a dream—it’s achievable with strategic planning and determination. First, leverage your existing professional skills.
My background in HR taught me that transferable skills are your greatest asset. Look for remote work opportunities that align with your expertise, whether through freelancing, consulting, or online platforms.
Financial preparation is crucial. Start by diversifying your income streams and building a robust emergency fund. Consider options like freelance work, online teaching, or creating digital products that can generate passive income.
Research affordable destinations where your money can stretch further, and be open to housesitting or other cost-saving travel strategies.
For those feeling stuck in their current careers, remember that your professional experience is valuable. Network with digital nomad communities, join online groups, and connect with families who are already living this lifestyle.
Websites and podcasts, like those offered by Our Offbeat Life, can provide practical insights and inspiration.
The key is to start small, be patient with yourself, and understand that this transition is a journey—not an overnight transformation.
Your skills, combined with careful planning and a willingness to adapt, can open up a world of incredible opportunities.
👉 While we have global health insurance for our day-to-day lives, we also elect travel insurance with SafetyWing for our spurts of fast travel adventure!
