Travelling the World as a Female Entrepreneur: 9 Lessons Learnt From 4 Years Abroad
As a female business owner/operator and full time digital nomad, my journey has taken me across the globe, blending my love for travel with the realities of running a business.
In this blog, I’ll share some of the top destinations that have shaped my entrepreneurial journey, as well as the lessons I’ve learned from being a solo female traveller.
How I Started my Digital Nomad Journey:
I first launched Gifting Owl to the world in 2019 with my Co-Founders in Brisbane, Australia. Gifting Owl is a global experience gifting company, where you can send a loved one on an adventure for their birthday, Christmas or any special occasion.
We had no idea, obviously, that 2019 would also bring with it once-in-a-lifetime border closures, travel restrictions and was arguably the worst time to launch a travel business since the GFC. Fast forward to 2021, we were still managing to weather the storm (just), and I decide to pack up my life in Australia to move to London for a couple of years, to be closer to our UK and European customers.
Spoiler alert… Life in London didn’t last long. Not when I realised that I could work from well, anywhere. I did a 2 week stint in Lisbon, as well as another in Croatia, where I packed my laptop and calculated that I was spending more money on my 4-share flat in London than my Airbnb in Croatia.
Of course it was a miserable January 2022 when I finally pulled the pin, packed my life into a backpack, and booked a month-long stay in Tenerife. The rest is history… What started in London led me to explore Europe, Latin America, and Southeast Asia, and I’m currently writing this very blog from Palawan, Philippines (ie. Paradise)!
I’ve learned countless lessons along the way—from navigating different cultures and overcoming challenges to discovering destinations that offer the perfect balance.
1. The Best Destinations for Work and Exploration
• Lisbon, Portugal
When I first decided to dip my toes into the world of digital nomad life, Lisbon, Portugal was my very first stop. I packed my laptop and booked a room at a hostel and a desk at a coworking space across the street.
It quickly became obvious why Lisbon is a top digital nomad location. With its thriving digital nomad community, reliable internet, and easy access to natural attractions like beaches and hiking trails, it felt like the perfect blend of work and exploration. The city’s safe atmosphere, great food, and vibrant energy made it an ideal starting point for my journey.
• Crete, Greece
Another of my favourite destinations for work and exploration is Crete, Greece. I’m a beach girl, so choosing a Greek island with reliable internet and a digital nomad community was a no-brainer.
It’s safe, there are weekly digital nomad meetups. I even hired a car and explored the island solo, oh what a feeling!
2. Destinations for a Perfect Blend of Productivity and Relaxation
• Tenerife, Spain
Finding a place that offers both the opportunity to work and recharge is essential as a solo entrepreneur. For me, Tenerife, in the Canary Islands, was the perfect mix. I spent my first month there, trying to escape the winter chill of the Northern Hemisphere. Tenerife is known for its year-round sunny weather and digital nomad community. I stayed in a quaint little town in the north called Garrachico, in an Airbnb ‘Villa Slowly.’ It had the perfect internet connection, kind local owners, a breathtaking view, and a peaceful atmosphere that allowed me to focus on my work while also connecting with nature.
• Limassol, Cyprus
If you’re looking for a destination that offers both natural beauty and a thriving digital nomad scene, Cyprus is hard to beat. I spent time there at ToHani, a co-living space, and was captivated by the stunning sunsets and crystal-clear beaches. The digital nomad community is huge, and the affordable cost of living made it an attractive place for both work and play.
Cyprus is also outside of the Schengen area, which is handy if you need a close destination that won’t use up those precious Schengen days.
• Lake Atitlan, Guatemala
Another standout destination was Lake Atitlan, Guatemala. Surrounded by volcanoes, Lake Atitlan is pure magic. It’s the ideal spot to reset, set new goals, and get creative. There’s a vibrant community of creatives, locals and travelers alike, and the reliable internet makes it a great place to work. The peaceful, picture perfect surroundings are perfect for those moments when you need to reflect or brainstorm.
3. The Power of Smaller Towns Over Big Cities
As someone who has spent time in big digital nomad cities like Medellín, Buenos Aires, and Santiago de Chile, I’ve learned that a thriving digital nomad scene doesn’t always mean it’s a great place for solo travel. While these cities offer plenty of coworking spaces and meetups, I quickly realised that I’m really not a city girl. In my experience, despite their active digital nomad communities, large cities can feel lonely, especially when you’re on your own.
Instead, I’ve found that I’m much happier and more productive in smaller towns, as long as there’s access to reliable wifi and natural attractions. I prefer places where I can connect with nature and meet like-minded people.
4. What to Look for When Choosing a Destination
When I’m considering where to live and work, a few factors come into play. First, I think about whether I’ll actually enjoy spending time there. I love being close to the water—I’m an amateur freediver, so places with access to snorkeling sites and marine wildlife are always top of my list. I also value destinations with rich cultural experiences and unique local offerings.
Next, I consider practical factors like reliable wifi, affordable accommodation, and easy access to basic amenities like grocery stores and transportation. Of course, safety is important, but surprisingly, it’s not always my top priority. Some of the most ‘unsafe’ places have turned out to be the most welcoming, and others I thought would be fine turned out to be a bit risky. It’s all about trusting your instincts and being prepared.
5. Challenges Faced as a Solo Female Entrepreneur
As a solo female traveler, safety is always a consideration. I really recommend doing your research on walkability in the exact area you’re staying. Sometimes a difference of just 1 or 2 blocks is the difference between staying in your Airbnb after dark every single night (I’m looking at you, Colombia) and being able to go out for dinner.
But in all honesty, some of my most memorable travel experiences have been in places that are not necessarily deemed ‘safe’ for solo female travelers. Interestingly, some places that I initially worried about turned out to be some of the most welcoming.
Another little lesson is that in my experience, many digital nomad ‘meetups’, networking events and language exchanges can be dominated by men, and feel more like speed dating than networking… It’s not to say you shouldn’t go, just try to find some female friends when you walk in the door. That way you can tackle the chaos together.
6. Networking and Meeting Like-Minded Entrepreneurs
Building connections as a solo female entrepreneur can sometimes feel daunting, but I’ve found that staying at independent co-livings has been one of the best ways to meet other like-minded people. Some of the best co-livings I’ve stayed at include:
- Sundesk in Taghazout, Morocco
- Lokal in Tbilisi, Georgia
- ToHani in Limassol, Cyprus
- Balu in Medellín, Colombia
- Flow Coliving in Puerto Escondido, Mexico
Even if you don’t stay at the co-living, these places often host networking events and meetups where you can connect with other digital nomads. It’s also a good indicator that if a town/city has a co-living/s, there’s a strong chance that other digital nomads are nearby, as well as good wifi.
If you prefer coworking spaces, I recommend attending as many events as possible, don’t just rely on office water-cooler chit-chat. These are great opportunities to meet people in a more relaxed setting.
7. How Solo Female Travel Has Helped My Career
Solo travel has impacted my career for the better, I’d say mostly by making me more adaptable. When you travel, similarly with business, situations come up daily that you need to problem solve and/or adapt to.
Traveling solo has also made me a quick decision maker. I’ve had to handle all sorts of situations on my own. From accidentally booking a month-long stay in a dangerous neighborhood in Santiago (don’t recommend!) to navigating language barriers and cultural differences. Sometimes you get it wrong, but the important thing is how you recover and learn from those experiences.
Ultimately, solo travel has helped me become more self-reliant and confident in my decisions, whether in business or life.
8. A Lesson on Privilege
The most important lesson is how incredibly lucky I am.
Lucky to be from a country that has given me so many opportunities. Privileged to have grown up without worrying about clean water, or my next meal. Growing up with access to education and health care. Growing up surrounded by a strong entrepreneurial spirit, and the chance to travel and explore.
Not everyone has the same privileges or access to resources, and I never take that for granted. Australia’s supportive environment for entrepreneurs, combined with the freedom I have as a solo traveller, has allowed me to build a business that connects with people across the globe. It’s a constant reminder that I am fortunate to have the opportunities that many can only dream of, and it motivates me to keep pushing forward.
9. The Strangest Part is Coming Home
It’s a feeling you long for when you’re abroad for a long period of time – the familiarity, the comforts of home. For me, that’s a surf club beer with my mates, a hug from mum, a swim in the creek, not having to open google maps, vegemite on toast… (argh, stop making me homesick).
But after months or years of travelling, the strangest part is always coming home.
People ask me “how was your trip?”, and expect I can give them a one sentence answer of how you spent the last years of your life in several different countries.
The transition back can be a little disorienting, almost like re-acclimating to a version of myself that no longer fits with the place. But it’s also a reminder of how many lessons I’ve learned and how far I’ve come.
Traveling the world as a female entrepreneur has been one of the most rewarding experiences of my life. I’ve learned that every place offers something unique, whether it’s the freedom to work in beautiful surroundings or the opportunity to meet new people and grow my business. There will always be challenges, but the lessons learned along the way are invaluable.
If you’re a female entrepreneur thinking about combining work and travel, my advice is simple: take the leap. You’ll never look back.
