Interview with Digital Nomad Copywriter – Cassandra

Last Updated on August 13, 2020 by Charmaine | The Canadian Wanderer

Cassandra Le is a copywriter and content creator at The Quirky Pineapple Studio. She moved to Madrid, Spain to become a location-independent entrepreneur. Her journey is so inspiring and it’s an honour to have her featured here today. I’ll let her take over!


What is your name and where are you originally from?

Hi everyone! I’m Cassandra. I’m originally from Washington, DC.

Where do you currently live?

I am currently living in the capital of Spain, in Madrid. I’ve lived in Spain before, in small towns outside of Toledo and Córdoba, but this is my first time living in the city.

Getting Started

How did you build up your copywriting career?

Before working full-time as a location independent copywriter and content creator, I lived in Spain as an English Teaching Assistant for two years. That’s where I first fell in love with the country, language, culture, and of course, the food! After working two years as an English Assistant, I returned home to the United States and found a full-time job as a Training Coordinator in a large environmental engineering/consulting company.

I worked as a Training Coordinator for a year and a half, and used my full-time salary to invest back into my blog turned online business, the Quirky Pineapple Studio! While working as a Training Coordinator, I interacted with international delegates from countries in Southeast Asia, Latin America, Africa, the Middle East, and Central Asia. I was even more inspired to work hard on my online business to visit the countries they came from.

After quitting my full-time job, I decided to pursue my business full-time. I am now a copywriter and content creator for businesses in the tourism and hospitality industry! My experiences with travel, event planning, and my studies have all led me to this job I created for myself, allowing me to travel and work anywhere I have reliable WiFi!

Madrid, Spain

Choosing Location

Why did you choose to work in Spain?

I chose Madrid, Spain because my boyfriend is here! He’s originally from Toledo, the first city that I lived in when I was here in 2014. That’s where we met, actually! We were in a long-distance relationship for a year and a half, while I was back home in the United States and he was here in Spain.

Madrid is the best city for the both of us because this is where his job is located, there is a large expat community for me, and since it is a city, there are a lot more opportunities to network and grow my business here.

What visa allowed you to stay in Spain?

Yes, I definitely do need a visa to stay! Currently, what we have is something called “pareja de hecho”, which is a government document that recognizes that we are in a relationship (or domestic partnership). Because my boyfriend is a Spanish citizen, this allows me to stay in Spain by receiving a residency card. The residency card is my visa to live and work here in the country.

Digital Nomad Path

Why did you choose this career/nomad lifestyle? Was there a turning point that led to the decision?

I feel like I’ve been dreaming about this for a LONG time. I’ve always been a blogger. I started blogging when I was 13 years old! I dabbled in a lot of different platforms, from Xanga, Myspace, Tumblr, Blogspot now turned Blogger, and finally, WordPress. I loved everything about blogging, writing, creating content, sharing photos, etc. I told my parents when I was 13 that I wanted to become a full-time blogger, so everything I’ve been doing since then, has kind of led me to where I am now.

I don’t think I was adamantly looking for the “nomad lifestyle” or to live it. Maybe at one point, I entertained the idea, but I do love having a home to come back to after a long trip. The turning point to pursue my blog/business, the Quirky Pineapple Studio, full-time came when my boyfriend and I were deciding what to do about our relationship and our goal to physically be together by 2018.

That’s when I really started to amp up my business, rebrand, re-launch, and start offering more services to allow me to work online and from anywhere. I knew that with the audience I was growing, I would be able to create a business and find work to keep me stable in Spain.

Her Experiences

What experience do you need to do your job? How did you get started?

Well, I think some experiences you’d need is understanding branding, marketing tactics, content strategy, and having personal experience in the blogging sphere and social media realm. Another aspect I find to be really important is having customer service experience and being able to work with people from all over the world with different backgrounds. That is really important! Also, understanding common trends in the tourism and hospitality sphere is very useful.

I’ve always been involved in the customer service industry since my parents own their own beauty business, and I was helping there. I’ve always had an interest in event planning, traveling, and writing, so from all those three topics, I’ve dived deeper into understanding them and seeing what works and doesn’t work. I also studied a Bachelors of Science in Hospitality Management in university and have experience as being a lifestyle and travel blogger.

I think from all of those aspects, it led me to create the Quirky Pineapple Studio and focusing specifically on the tourism and hospitality industry.

Cassandra Le, founder of The Quirky Pineapple Studio

The Best and Worst Parts

What is your favorite thing about the job?

My favorite thing about this job is being able to work with people from all over the world and bringing their vision to life! I love having client meetings and seeing them get SUPER excited about their project but not really having a clear idea of how to get there. That’s where I come in and work with them to develop their brand story, come up with content, and create a tailored strategy for them!

The best part is taking all of their jumbled ideas and words, then writing out their website copy in a way that speaks their brand’s message and shares the heartfelt passion behind it! The hospitality and tourism industry is EXTREMELY reliant on human interaction, and that’s exactly why I love working in it.

What is the least favorite thing about the job?

I wouldn’t call it my least favorite thing, but probably the part about the job that isn’t always fun is all the backend work that most people don’t see. It’s when I have to go in and log details about a client and their project, creating invoices and contracts, or trying to figure out my taxes and finances!

All of those things are necessary to keep my business floating and on track, but those aren’t the creative things I love. They’re things I HAVE to do to make sure that I can keep running my business!

gold ipad beside stylus
Photo by Jess Bailey Designs on


What does a typical day in your job look like?

Since I’m still new at this “digital nomad” lifestyle, I am trying to figure out the best way to structure my days. Currently, it’s a lot of trial and error to see what I need to do and what works best for me and how my energy/brain functions.

This is what is currently working so far:

  • Wake-up at 7am (Don’t actually get out of bed until 7:30/8am)
  • Breakfast, setting goals for the day, and morning journaling
  • In the “office” by 9/9:30am (this usually varies depending on what time I wake up, but my goal is to be in the “office” by no later than 9:30am)
  • After this, my day usually varies on what type of work I have and which project deadline is approaching. I usually switch from checking emails, writing blog posts/planning out my own content calendar, self-promotion/looking for leads, and client work.

For me, my energy levels are usually highest in the morning. Towards the afternoon, around 5/5:30PM, is when I start getting restless and my energy levels and motivation are dwindling. I try and close up my “office” (aka, shutting down my laptop) and answering the last email by 5:30/6PM.

Final Advice

What is your advice for someone who wants to do something similar?

My advice would be to figure out “why” you want to do this in the first place. Do you want to travel the world? Do you love the job that you’re doing? Why do you want to create a location independent lifestyle? If any of your answers revolve around “because I want to be like…” – then I’m going to tell you to go back and think about your answer again.

It’s definitely NOT easy to do this, and I’m learning that now. Everyone really glamorizes having a location independent lifestyle or being their own boss, but it’s actually quite lonely! In the end, I know my reasons for pursuing this type of lifestyle, and why I wanted to create this business. I think having that in place before doing #allthethings to get there to “be like someone else” is important.

Jobs on the Road - Copywriter, Content Writer and Blog Coach Interview with Cassandra Le, Founder of The Quirky Pineapple Studio. Work Abroad | Remote Work | Entrepreneurship | Madrid, Spain


Cassandra is a copywriter and brand/blog coach for the creative, fierce soul. She works with businesses and entrepreneurs in the hospitality and tourism industry, to help them hone in on their voice and connect with their community to increase visibility and profits. You can usually find her frolicking through cobble-stoned streets, scouting out the best street food, or blogging at The Quirky Pineapple Studio. She believes that there is a fierce diva in everyone and is on a mission to make sure others harness their confidence!

To learn more about her, you can visit her Facebook page, Instagram or Twitter.

The Jobs on the Road is an original series that focuses on how real people make money on the road while traveling. This series is meant to inspire and to show you how real people can maintain the best of both worlds: traveling and building a career. If you are interested in participating or to learn more about the project, please view here