Preparing for a Digital Nomad Experience

Becoming a “digital nomad” was NEVER part of my plan.

I distinctly remember in the 6th grade, when we went through an exercise to plan where we saw ourselves in 5-10 years, I wrote about how I moved to New York City and owned a luxurious apartment. I imagined myself in the fashion industry and was a writer or editor. In my mind, I envisioned myself as a renowned editor or writer working with publications like Vogue and Elle.

Now, I’m preparing for a digital nomad experience in Latin America with Job Trippin’ for 2 months.

I work as a copywriter and content strategist for businesses in the tourism, hospitality, and gastronomy industries and I do NOT live in a luxurious apartment in New York City. Instead, I find myself in a 35 m² home with my boyfriend in the hustle of Madrid, Spain. So, when I talk about being a digital nomad – this was NOT part of the original plan, but dang, it’s been WAY better than what I imagined!

READ: First Month in Spain & Home Tour!

While I’m prepping for this experience in two Latin American countries, Argentina and Chile, it’s time for a bit of reflection on everything that’s lead me to this point – because you know, I’m emotional and think it’s important to share this!

I break down my step-by-step process, emotions, and thoughts to prepare for this digital nomad experience – because this will be my first time!

Thoughts & Emotions as a Digital Nomad

While I don’t consider myself to be a “true” digital nomad (I don’t move every few months), I do consider myself location independent. To me, being a digital nomad sounds extremely stressful and tiring! I definitely prefer having a “home base” and traveling every so often on shorter trips, than long trips and living somewhere new. I’m also an extrovert, but it’s definitely tiring to continuously put yourself out there! I’m also not a fan of small talk or shallow conversations, so much so, that I would rather be by myself than have small talk with people (yes, I know, I sound cynical).

Since this will be my first time traveling as a “real digital nomad”, I’m EXTREMELY RELIEVED that I don’t have to do any planning, booking, or Googling during the two months I’ll be in Latin America! Job Trippin’ will be taking care of all the logistics and planning for me – so all I have to do is show up and enjoy! (Hallelujah, less stress!)

Quick note: I know I could probably plan a digital nomad experience in Latin America by myself (and it would be cheaper), but since this is my first time in Latin America AND traveling as a digital nomad – I feel relaxed and excited that someone else is going to take care of everything for me!

Expectations as a Digital Nomad

I’ve taken work on the road before – while on small weekend trips, while traveling through the south of Spain, or working from the actual road and writing out copy and content for clients (without Internet, hah); but this will be my first time traveling as a digital nomad and moving so often! Job Trippin’ is the only program for remote workers focusing on Latin America, and their trips last for 6 months in 6 different cities.

I’m a bit nervous about the experience and honestly, don’t know what to expect! These are some of my ideas:

  • Meeting remote workers or other digital nomads from around the world
  • Learning about different types of jobs that are able to be taken on the road
  • Living in different cultures and expanding my network
  • Getting a bit annoyed with group travel (I’m really not a fan, to be honest)
  • Practicing Spanish with different accents and idioms
  • Traveling and exploring new countries and cities
  • I will most likely get tired of moving (or not… who knows!)

READ: Traveling in a Group (& How to Survive!)

My goals for the two-month trip are:

  • Meet with businesses in the tourism, hospitality, and gastronomy industries in Argentina and Chile
  • Work on The Quirky Pineapple Studio’s visibility strategy
  • Secure at least 4 new clients from Argentina or Chile
  • Collaborate with 3 other people who will be participating in this trip

Looking to amp up your website copywriting to attract English speaking tourists or expats to your locale? Let’s set up a time to chat, so we can get your website ranking with organic SEO and connecting with your audience! Schedule a Clarity Call today!

How I’m Preparing to be a Digital Nomad

During my time in Argentina and Chile, I’ll be going through a hybrid of work and travel! I will continue to work with clients and onboard new ones – but I can’t forget the fact that I am also in a new country and continent!

So, just because I’ll be traveling doesn’t mean that work has to (or can) stop. I’m prepping everything ahead of time so that my systems are seamless and my clients won’t be able to tell that I’m working from my coliving home or hiking through Patagonia!

Here’s what I’m doing to prepare:

  • Automate as much as possible (emails, invoicing, contracts, etc. – I’m using Dubsado, to keep track of all these things!)
  • Plan ALL of my content ahead of time (I usually plan at least 3 months out)
  • Batching all content (blog posts, newsletters, social media posts, etc.)
  • Schedule my content to be shared (this comes after batching!)
  • Set up auto-responders and automated workflows (also through Dubsado!)
  • Ensure my meetings and calendar is up-to-date with timezones and time differences (my scheduling tool for that is Book Me Like a Boss)

Business doesn’t stop just because I’m traveling, and it is DEFINITELY unprofessional to make your clients wait or have a poor experience because you were exploring a new country and had limited access to WiFi!

READ: Work & Travel, Glamorous or a Pain in the Ass?

Digital Nomad Programs That Make Life Easier (but really)

There’s a lot that goes into becoming a digital nomad. If you’re like me (a bit of a control freak), having someone plan everything for you makes life A LOT easier. The excitement and recent trend of becoming location independent or a digital nomad have recently peaked – the rise of programs to help digital nomads and location independent workers has grown!

Job Trippin’ is just one of the many programs that make the transition into this lifestyle easier because they’re taking care of everything for you! The program cost includes:

  • Transportation between cities in the planned itinerary
  • Private rooms in coliving spaces (hello, PRIVATE ROOMS = PRIVATE BATHROOMS!)
  • Coworking spaces with 24/7 Internet access
  • Spanish lessons (hallelujah – probably what I’m most excited about!)
  • Medical insurance (very important, y’all)
  • Networking opportunities and group trips!

The only things I need to take care of on my end are:

  • Flights to and from my first city and last destination
  • Personal food and shopping costs
  • Any trips I decide to personally take on my own

I’m super excited to be heading on the road with a group of other remote workers and digital nomads, learning from them, and exploring two new countries! I might not be the renowned writer or editor for large publications like Vogue or Elle, but I’m able to work with businesses in three industries that I wholeheartedly believe in and enjoy – while being able to create a lifestyle that I love.


Make sure to keep up with my adventures as I’m discovering Buenos Aires, Argentina and Santiago, Chile on Instagram! I’ll be sharing the entire journey through Instagram Stories! 

Tourism, hospitality, or gastronomy business in Buenos Aires, Argentina or Santiago, Chile? Let’s work together to revamp your website copy and create a content strategy to build a community of loyal clients! Schedule a Clarity Call to see how we can work together!

*This post is sponsored by Job Trippin’ but all opinions are my own. This post also contains affiliate links. This means, if you decide to purchase anything through them – they help keep TQP Studio going! 

Have you traveled in a digital nomad program before? Got any tips? Share them in the comments below as I prepare for this adventure!

Enjoyed this post? You might like these, too:
Live & Work Abroad as a Female Entrepreneur Pt. 1
Live & Work Abroad as a Female Entrepreneur Pt. 2
How NOT to look Dirty While Traveling
Are You the Snobby Travel Friend?

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The digital nomad experience is filled with... excitement, frustrations, stress, and a lot of planning. That's why programs like Job Trippin' make it easier -- The Quirky Pineapple Studio

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