How to Live and Work Abroad as a Female Entrepreneur

Guest Post by Cassandra Le:

The fierce woman has arrived and she’s taking on the world!

She’s looking for more out of life than what’s expected of her. She doesn’t want to take orders from others and she isn’t playing into typical stereotypes. She’s kind, intelligent, bold, fierce, AND filled with adventure.

Her goal? A job she loves that allows her to live and work abroad.


Well, it just so happened that I decided to do all of that.

To be honest, I don’t think I knew I wanted this to be my lifestyle until I had a little taste of what it was like to live abroad.

For two years, I lived and worked in Spain. Afterwards, I moved back home to Corporate America and did all the things my friends were doing. I went out, I worked a 9-5 job, and I even thought about buying a car!

I then realized this wasn’t the lifestyle that I wanted, so I quit my full-time job and started my own business. To add to the excitement, two weeks later, I hopped on a one-way flight and moved permanently to Madrid, Spain.

How’d I do it? I’m sharing everything I needed to figure out beforehand, during the moving process, and what it’s like living abroad in a new country, culture, and whole other language!



If you’re like me, working for someone else just isn’t your cup of tea. And if we’re basically soul sisters – travel always calls at you.

When I started my business, I knew I wanted something that allowed me to travel and work. A job that only required my laptop, reliable WiFi, and an external hard drive (those are important, by the way), so I turned my lifestyle and travel blog into a copywriting and content strategy virtual studio for businesses in the tourism and hospitality industry. Now, I work with clients from all over the world in both English and Spanish!


How to live and work abroad as a female entrepreneur


You’ve already started your business, now it’s time to figure out if you can take it on the road with you! The first question to ask is where do most of your clients come from? Can they be found online or are they specifically based in one area? Here are some resources I’ve used to find clients online:

• Facebook
• Facebook Groups
• Instagram
• Pinterest
• YouTube
• Word of mouth (referrals or recommendations)
• Mastermind groups (paid or free)
• Membership sites (paid)

And if you’re unsure if your business can be taken abroad, these are examples of jobs that can be taken on the road:

• Writer
• Photographer (portrait photography, travel photography, etc)
Graphic Designer
• Digital Marketer
Website Developer
• Coach (productivity, life, success, business, relationship, etc)
• And more!

Most of these professions allow you to work from anywhere, with anyone.


Probably one of the hardest decisions I had to make was picking a new place to live. If you are from North America, we have so many options to live and work abroad – either through agencies, companies, or the government! Although most of these positions will require that you work another job, it’s still an opportunity to live abroad, explore a new culture, and have time to work on your business.

Some options for North Americans are:
• Working Holiday Visa (to Australia, New Zealand, or Ireland; available up to ages 30-35)
• Auxiliares de Conversación (program to teach English in Spain)
• Teaching English abroad (in Europe, Southeast Asia, Latin America)
• Travel & Work companies (for digital nomads)
o Remote Year
o GoBeHere
o Job Trippin’
• Coworking/co-living spaces (worldwide!)
• Etc.

The Visa Paperwork

As a North American, we have it a bit easier with a strong passport. United States citizens are able to visit countries in the Schengen zone for up to 3 months. Afterwards, you will need to leave the Schengen zone to “reset” your time. The Schengen zone includes MANY countries in Europe, allowing US citizens to travel around without needing to leave or go back home.

Something important to consider is how long you want to stay abroad and if you plan on permanently moving or becoming a “digital nomad.”

For me, my fairytale love story brought me back to Spain. I knew that if I were to move, it would be permanently and I needed to bring my business with me. My visa is a bit more complicated; because my boyfriend is from Spain, we needed to figure out the logistics to have me stay permanently in Europe.

If this weren’t the case, I’d be calling myself a “digital nomad” and moving every so often!

*Please consult an immigration lawyer in regards to the type of visa paperwork that you will need to take your business abroad or travel as a business owner in different countries.


Time to brand yourself.

Is travel or “new adventures” part of your brand? Is it something that your clients or audience know about you?

Some might say this part of living and working abroad isn’t as important, but I disagree. If your brand doesn’t already include travel as one of its values or inspirations, your audience might be confused about what you do or why you do it.

If your audience is confused, your future clients will be confused. Many clients may misinterpret your move and be unsure if you’ll be able to carry out responsibilities abroad or if you’re “just on vacation” for a long period of time.

Some tips for adding travel to your brand (from a copywriter and content strategist’s point of view)

• Talk about mini trips you’ve taken in your home country
• Introduce the excitement you feel from travel, adventures, exploration
• Share how new cities, countries, or cultures influence your work (or where you draw your inspiration from in general)
• Use social media to take your audience around your hometown – like a small tour

Make sure processes are in place before you can live and work abroad

When you travel and live abroad, you’re adding time zones to your schedule and your work. What does that mean? You could be in a different time zone than some of your clients.

Just because you’re sleeping doesn’t mean that you can’t be marketing your business! And just because your clients are sleeping, doesn’t mean that you can’t create processes to capture leads, grow your business, and more.

Certain processes need to be in place to make life easier: services, work, content creation, lead generation, etc – so that we’re not behind the computer ALL DAY!

Prep and automate as much as possible

After creating and defining processes, which ones can be automated and built into systems? I mentioned it earlier, but if you’re taking your job on the road – it’s time to take into account time zones and currencies.

Here are some processes that I automate and use systems for:

• Meetings
• Lead captures
• Automatic responders
• Automated invoices for current clients
• Social media scheduling

The last thing we want while living abroad is to spend all of our time behind our laptop – right? If adventure calls – we must answer!


How to live and work abroad as a female entrepreneur


Systems make sure our businesses work FOR us, while we’re able to save time and enjoy life – one delicious wine and beautiful landscape at a time!


While working and living abroad seems like a dream – it also means keeping track of a lot more details. As I transitioned to a different time zone than many of my clients, I also realized that I will be paid in different currencies.

Spain is part of the European Union, so I pay everything in Euros. My clients, however, are mostly from the United States – so I get paid in dollars. Also, what do you do about TAXES? There are sales taxes, VAT, income tax, social security tax, etc. What happens now?

I’ll break down some simple details to keep track of and a few resources I use, below.


My recommendation is find an accountant who works with “digital nomads” or expats. They’ll be able to help you understand the tax systems and what to do about your finances. (Also, where you will need to pay your taxes to – your home country or your new country)


Figure out how you will invoice people. For me, this means understanding where my clients are from. If they’re from the European Union, I bill in Euros. If they’re from the United States, I bill in dollars.


How are you getting paid?! Where are the transfers and deposits going?

*Again, please check with an accountant to see what to do in this situation, also take into account where your business is legally registered

Unfortunately, I do not have all the answers to tax and invoicing questions, but I DO have resources for getting paid. You know, the important things! Below are some websites and apps that I use to keep track of my own finances, transferring money, and more.

These are some apps and websites I use:

Transferwise (my FAVORITE website to transfer money, without all of the horrible commission rates and a great value for the exchange rate)
• Revolut (an online bank system, that even gives you a credit card)
• Stripe
• PayPal (US and Spain)
• Mint
• Square

There are so many options for payment, now that online businesses are becoming increasingly more popular! It’s best to do your research to find which apps or websites are best for the country that you live in. If you do consider moving to another country more permanently, I do recommend opening a bank account there.




Now that I have “officially” settled into my new home, I’m learning how to adapt as a business owner and expat.

Who thought it would be a great idea to start a business and then move across the Atlantic Ocean? Me, it was I.

Who else thought that moving to a country where English is NOT the native language would be a great idea, while also building a business? Again, me, my idea.

I would not recommend doing what I did to anyone, because let me tell you, it is hard. These past few months have been a HUGE learning curve. Here are some tips to make adapting and transitioning a little less rough and a bit smoother. (You know, so you’re not crying at home and asking yourself wtf are you doing…)


Moving to a new place means loneliness creeps up and gnaws at you. To make the transition easier, try to find a community (or various communities) that you can connect with. In any large city, there are numerous groups to connect with people over a common interest.

If you’re like me, you love meeting people. If you’re also like me, shallow connections actually drain you – and you’re looking for more meaningful relationships and friendships. Totally normal. One thing that I consistently have to remind myself is: RELATIONSHIPS TAKE TIME AND SO DO FRIENDSHIPS. Be patient with yourself.

These are some tools that I use to find online and in-person communities to connect with:

• Local Facebook groups
Digital Nomad Girls
• Local meeting spots
• Coworking spaces
• Local events in the area

*An important tip: don’t be afraid to hang out with other expats, as long as your friends are not only expats! I was so scared to hang out with only English speaking expats because I didn’t want to be in an “expat bubble”, I wanted to integrate myself into the culture and make local friends. It takes time – I’m still working on it!


Well if you’re taking the plunge to move your life across any ocean into foreign land – *high five* because the adventure is about to start!



From trying to grow my business and adapting to life as an expat, I have learned that I need schedules, hard deadlines, and a little accountability in my life. Transitioning to a full-time business owner requires mindset work and developing structure. How do you add structure to your life when you’re abroad AND working full-time on your business?

Things I’ve had to develop for myself to be able to enjoy my new home AND build my business:
• Daily and weekly schedule
• Places to leave the house and go to (coworking space, cafes, etc.)
• Understand the processes I have and refine them as I work/live my life
• Integrating “exploring” into my weekly schedule
• Patience, lots of patience
• Expat AND local community
• Morning and nighttime routines
• Networking events once or twice a month (for entrepreneurs, biz owners, expats, creatives, etc. — inclusive of coffee chats)

Some days I get to cross all of these off my list. Other days, I think that I am totally doing this wrong! The structure gives me balance and motivation, the free time gives me space to be creative and find inspiration. Try to test and see what works best for you! But, don’t spend all your time behind your laptop – you are in a new place, after all!


Of course when you move abroad, cultural differences are HUGE, which can lead to culture shock. I’ve dealt with culture shock and reverse culture shock, when moving back to your home country and feeling trapped. There will be days you feel sad, actually, there will be a lot of days you feel sad – totally normal.

Take into account the type of culture that you live in. What makes it unique, what are their values, what are their customs, etc? This is something I needed to consider when I decided that I wanted to try and break into the Spanish market and work with businesses based in Spain.

If you’d like to do the same in your new host country, some things to keep in mind are:


• What is the buying culture?
• What is the business culture? How do they run their businesses?
• How does the culture value work and free time?


All of these factors add to cultural differences in running a business and working with international clients. I am still working on rewiring my brain to understand Spanish consumers and what they look for, what they want, and the value they place on certain aspects. How can you use your home culture to leverage the type of business you’re running abroad?


What I should have said from the beginning was have patience and give yourself grace. It takes a lot of courage to pack up your life and move it anywhere, let alone another country! I’m learning that to live and work abroad takes a lot more tenacity than I expected and every day I learn something new about my host country and myself.

But, you’re a fierce woman and your mission is to take on the world!

There are a lot of other factors to consider, before working and living abroad, but this is a short breakdown of some important details to consider before making the decision.

And if you’ve already taken the leap, cheers to you! It’s time for the adventure!




Cassandra is the creator of The Quirky Pineapple Studio, a virtual studio that offers copywriting and content strategy for creative souls in the tourism and hospitality industry. Cassandra works to create a loyal community of clients through content and experiences. When she’s not working away on her laptop, you can usually find her exploring Madrid, taking short adventures with her boyfriend, or gallivanting through cobblestoned streets for the perfect Instagram shot!

Social media links:
Website – www.thequirkypineapple.com
Instagram – instagram.com/tqpineapple
Facebook – facebook.com/thequirkypineapple
LinkedIn – linkedin.com/in/cassandra-le


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