How Nomading Has Shown Anny Wooldridge What’s Most Important in Life

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This post is brought to you by a few of Anny’s travel must-haves: her laptop, an external hard drive, headphones, and a purse with coins from her travels that often comes in handy.

This is the latest interview in a series featuring digital nomads talking about their lives and lessons (click here if you want to be interviewed). The goal is to help demystify the process of making money online, wandering the world, and living an unconventional life!

Anny works as a freelance writer and primarily focuses on travel content. She shares our love of learning by experiencing new cultures. Be sure to check out her website if you’d like to read more insights about working abroad or about living in Columbia!

Thank you for sharing your story with Freedom Is Everything, Anny!

Key takeaways from Anny’s interview:

“If you have any desire to start nomading… go. You won’t regret it! That’s not saying it’s easy as being nomadic can be lonely, scary, and very intimidating, but it can also be exhilarating – you will definitely find out things about yourself you never knew before, and be prepared for life to never be the same!”

“Travelling around different countries being nomadic has taught me vast amounts about the world: every country has something different to offer. Travelling to other countries and experiencing different cultures gives you an alternative perspective on how people live their lives and shows you what’s possible and also what should be important.”

“It’s never smooth sailing, everyone has their own timeline, and it’s easy to get aggravated at things not coming together or getting rejected for pitches, or hearing nothing back. But consistency is key, keep plodding along, and things do come together. Try and fail, each failure will teach you something, and knowledge and experiences are what separates you from the rest of the field.”

“Be yourself – you are enough. In a world filled with filtered social media posts and images, ideas of how we should live, different definitions of success, and the idea that to be successful, you have to get the best car, get married, buy a house, etc. This isn’t the case; your path is your path, not anyone else’s, don’t let people tell you how to live.”

Table of Contents

Introduce yourself! 🙂 Who are you? What do you do for work? And what is your nomadic story?

Anny Wooldridge smiling while wearing sunglasses and a large sunhat with a garden behind her

Hi! I’m a freelance travel writer and marketing manager originally from a small city in England called Norwich. That being said, since graduating from University in 2013, I have never really stayed there for more than one month at a time – well, that was the case until the pandemic. Since 2013 I have lived and worked in Greece, France, and Colombia before becoming nomadic in May 2017, after living in Colombia for two years and establishing my freelance writing career.

My writing focuses on travel, except for a few months, which I spent creating content for a marketing firm. I love showcasing a country and exploring and creating content around the people that I meet. My writing has appeared in Matador Network, Culture Trip, World Nomads, and We Are Travel Girls, and I have also completed projects for Google and Google Trips, among others.

I’m also an editor, copywriter, and marketing manager; I work helping companies with newsletters, social media, creating graphics, and all things content.

Currently, I am living in England and waiting for the world to open up. Since becoming a digital nomad in May 2017, I have visited and travelled extensively in South America, Europe, Asia, Africa, and North America.

I love to visit new countries and visit the friends that I’ve made all over the world. You can often find me on my laptop working from anywhere and everywhere, in a Crossfit gym, drinking coffee, or water skiing.

What inspired you to start nomading? And how has nomading changed your perspective on life?

Anny Wooldridge looks at ancient ruins in Italy

What a question… Ever since I can remember, I have loved to travel. As a kid, we took family trips all around the world. I loved to get away from sleepy Norfolk and discover a new culture, wake up somewhere yet to be explored and meet people from all around the world with incredible stories.

I did the ‘typical’ go to University, get a degree, and apply for graduate jobs (I got rejected from them all – thank goodness). Upon graduating, I stumbled upon a job teaching beginners to water ski in Greece – which of course, I jumped on. I then found every job I could find that would allow me to travel, from being a nanny to being an English teacher in Colombia. It was only when I was living in Colombia that I started writing my travel blog to showcase my daily life in Colombia and stumbled upon travel writing.

Nomading hasn’t just changed my perspective on life; it has changed every aspect of my life in a way I could never imagine, most of which have nothing to do with my business or work. Each and every country I have visited has shown me something new, taught me a lesson, or opened my eyes to a new culture and a new way of living.

If you had told me while I was at University that I could work anywhere around the world from a laptop, I wouldn’t have believed you. Nomadic was something I never imagined I would ever be or even thought was possible. Growing up, you are taught that if you want to work an office job, your job has to be in an office – but that’s not always the case. And the pandemic has emphasised that. 

I always say I was working from ‘home’ before working from home was normal. Life is for living, and whatever the reason for doing your job, it’s not the be-all and end-all of life. Being nomadic has taught me mostly that work-life balance is essential and easier than you think.

Travelling around different countries being nomadic has taught me vast amounts about the world: every country has something different to offer. Travelling to other countries and experiencing different cultures gives you an alternative perspective on how people live their lives and shows you what’s possible and also what should be important. 

This quote by Nomadic Matt kinda sums up how I feel when travelling – “The more you travel, the more you realise that daily life around the world is exactly the same. The why is never different. Only the how. And to me, seeing those differences is what excites me the most about travel.”

Please tell us the detailed story of how you started your freelancing business.

Anny Woolridge with her back to the camera and her arms in the air while standing atop a tall hill that overlooks Bogota, Columbia

I started writing a travel blog and creating social media pages after my friends kept asking me lots of questions about Colombia. They couldn’t believe the images and content I was producing. And it kind of all started from there. I began to write more and more articles on my blog about different travel experiences and places. I then came across an advert from a top online travel publication that was looking for a Colombia destination writer. 

So while living in Colombia, I wrote over 90 Colombia-related articles for this company and used that work and my travel blog as a portfolio to pitch and gain other freelance content writing work. During this time, I was also working as an English teacher, but fortunately, I was working around 5 hours a day, so I could spend the rest of the day working on other freelance projects. Eventually, I gained enough steady freelance writing work that I was able to stop teaching English and go full-time into freelance writing. 

Since launching, what has been most effective to acquire/retain clients?

A portfolio of work is hugely important, whether that is on a blog when starting or working for other clients or publications when more established. I have found that mostly one thing leads to another; getting a byline in a major publication comes with a certain level of authority.

Networking and communication are equally important, in addition to being kind, honest, and open. I have had clients that I have written content for, created social media campaigns for, and worked with steadily since August 2017. Being yourself, producing good work, and being reliable are some of the ways I have kept these projects ongoing for such a long period. 

Creating networks, having an online presence, and maintaining a portfolio are ways I have continued to gain bylines in publications.

What advice would you give to someone who’s thinking about nomading?

Anny Wooldridge on a coffee farm in Medellin, Columbia picking coffee berries into a wicker basket

If you have any desire to start nomading… go. You won’t regret it! That’s not saying it’s easy as being nomadic can be lonely, scary, and very intimidating, but it can also be exhilarating – you will definitely find out things about yourself you never knew before, and be prepared for life to never be the same! 

Before moving to Colombia and again when changing to being nomadic, it was scary, and I was filled with anxiety, but that’s normal. It’s similar to any other time you leave behind your comfort zone or normal routine. But always in the back of my mind, I was just a plane ticket away from home. I always had the cost of a plane ticket set aside if I had the desire to leave my nomadic lifestyle behind, a safety blanket if I ever needed it. 

Before I became nomadic, I had an established website and regular travel writing features, so I had a steady income stream. I think it’s very important to have something stable and a form of income before jetting off long term. Or at least enough money to survive one or two months without working, which takes away some of the anxiety of the unknown. 

The internet has made the world hyper-connected. I have made friends all around the world through the power of social media through Facebook groups, expat groups, and local meetups. Often a simple Facebook search for expats or ‘digital nomads in x’ will give you no end of page and group options. I love meeting local people. In places like South America, I have found that the locals reach out and want to get to know you, ask questions about your country, and show you theirs. 

What is unique about the way you travel, and what advice do you have for someone that wants to travel with a similar style?

I love travelling long-term and really getting to know a place instead of just spending one or two weeks somewhere. Setting a base for a month or two allows you to take your time exploring, and because I am always working simultaneously whilst travelling, I often spend long periods of time on my laptop and need extra time to explore. 

Usually, I tend to get up early and explore before the masses arrive or work early and take a mid-day break to explore and get back to work in the evenings. But it totally depends on workload, or if there is something unique worth checking out in the destination on a given day. 

What are the 2-3 favorite places where you’ve lived/traveled to and why?

A side view of Anny Wooldridge as she stands on a hill that overlooks the city of Cartagena

Colombia will forever hold a special place in my heart. From my first trip to my last, each and every time I land in Bogota, it feels like home. I lived in Bogota continuously for a period of almost two years, which is where I started teaching English. I started my travel blog there, and I got my first freelance writing jobs there writing about Colombia. 

It’s a country with a troubled history and horrible reputation still, but it is one of the most biodiverse countries in the world. I have visited metropolitan cities in Colombia, the Amazon Rainforest, Caribbean islands, the thriving, colourful Caribbean town of Cartagena, the Pacific Coastline, rainforests, deserts, plains, snow-capped mountains, and more. 

Colombia, and specifically the city of Medellin, has recently become a favourite with nomads, and it’s easy to see why – with fast internet speeds, lots of things to do and see, and a greater value for money than western countries. 

Choosing another two is so hard. I have visited so many incredible places. But two more that stood out are Spain and Portugal.

Spain is another one of my favourite countries to be based in. There are cities filled with culture and history. There’s also so much delicious food, great restaurants, and the incredible cities of Barcelona, Cartagena, and Valencia should be on everyone’s bucket list.

Also, Portugal was another one of my favourite countries mainly because of the beautiful city of Lisbon, along with so many other coastal cities and of course nice weather year-round. Lisbon is high on my favourite cities list!

I’m also in love with Dubai, Egypt, Australia, and Peru. 

As a woman, what should other people who identify similarly (and who haven’t traveled much) know about traveling/nomading?

Anny Wooldridge standing on an empty dirt road in a village in Peru with homes on both sides of the road

As a woman travelling (often solo), it can be very intimidating, anxious, and really not nice at times, but the reward is greater than the risk. 

Before travelling to a new place, I read up on the culture, safe areas to stay in, what is acceptable or unacceptable to wear, and do’s and don’ts when in that specific city. There aren’t many places you will visit that you can’t find information about before you visit, whether on a blog or a simple Google search. 

Specifically, before arriving in a new country, I always check the airport’s transportation options to my hotel or apartment. For example, some South American countries I have visited have taxi scams or ‘fake taxis,’ so checking the safest option of where to get registered taxis or how to identify scams is essential to avoid any problems.

Another thing I do is to take note of how the locals behave; for example, on public transportation, are locals wearing their bags on their front so they can see them? This often shows that there is a problem with people stealing things from bags, for example— things like this and just keeping your wits about you and trusting your gut. These things are minimal compared to the joy and experiences gained through travelling.

What is one of your favorite travel stories/experiences?

Anny Wooldridge's back as she overlooks a lush tropical valley in barichara

When I lived in Colombia, one of my newly made Colombian friends asked me if I wanted to join her on a trip to the Amazon rainforest in like two days. I jumped at the chance and ended up living with and experiencing what it was like to live in the middle of the rainforest for four days. Sleeping in hammocks, cut off from the rest of the world, and staying in a family’s house, truly living as they do.

What digital tools do you use for your work/business?

I like to think I am pretty organised: I use Google Drive, Asana, Zoom, Apple Calendar, and Slack for different clients and to keep things orderly. I also like to use a good old-fashioned paper diary and notebook for daily tasks. I have recently joined a Digital Nomad Girls Inner Circle group, an online co-working space for female digital nomads. 

What scale is your business at today, and what are your future goals?

Anny Wooldridge holding a plastic cup with an orange drink in front of the city of Guatapé in Columbia

Currently, I have two or three projects ongoing at the same time, including the two regular clients I have had since 2017. I am continuously pursuing new publications and pitching new stories, in addition to updating my portfolio and searching for new angles. 

My income is in line with my peers in the UK, and it often varies from month to month depending on projects. I have also been lucky enough to make money through press trips or familiarisation trips with one of my long-term clients allowing me to travel to different countries and gain new experiences while gaining subsidised or complimentary travel.

In the future, I would love to continue working with my current clients and gain bylines in more major publications to continue to increase my portfolio. I love where I’m currently at and am excited about what the future might bring and be for travel when people start hitting the road again. And I have lots of bucket list destinations!

For someone interested in becoming a freelancer in your field, what’s the best advice you would give? And what books, podcasts, thought leaders, or other learning resources do you recommend?

It’s never smooth sailing, everyone has their own timeline, and it’s easy to get aggravated at things not coming together or getting rejected for pitches, or hearing nothing back. But consistency is key, keep plodding along, and things do come together. Try and fail, each failure will teach you something, and knowledge and experiences are what separates you from the rest of the field. 

Freelance websites such as Upwork are a great way to get started no matter what industry you are in, with a large variety of jobs in multiple industries. 

For travel writing-specific resources, the Matador Creators is a great place to find writing jobs as they publish what pitches they are looking for, particular articles, or on a specific destination. Other great resources are the Sian Meades-Williams newsletter, a weekly newsletter listing jobs or editors looking for specific pitches. Talking Travel Writing is great for tips and tricks within the travel writing industry. 

For more generic freelance writing jobs, Problogger and PitchWiz are great starting points. 

If you only had a few minutes to live, what are the most important life lessons you would share with the world?

The back of Anny Wooldridge's head while she looks over a terraced area in the lost city of Columbia

Be yourself – you are enough. In a world filled with filtered social media posts and images, ideas of how we should live, different definitions of success, and the idea that to be successful, you have to get the best car, get married, buy a house, etc. This isn’t the case; your path is your path, not anyone else’s, don’t let people tell you how to live. 

I love this quote by Benjamin Franklin: “Some people die at 25 and aren’t buried until 75.”

What do you travel with that you couldn’t imagine traveling without?

Some things I always travel with are:

  • My Laptop and external hard drive
  • Headphones
  • I have a purse filled with coins from all over the world, which has helped me out on numerous occasions.
  • My diary and a notebook
  • Google maps (offline)
  • Google translate (offline languages)
  • VPN – Express VPN
  • Travel Insurance – I like long term travel insurance from providers such as World Nomads
  • I have a small makeup bag filled with things I have picked up on my travels and printed out images. 
  • I always take eco-friendly products on my travels, such as a reusable water bottle, shampoo bars, and washable face pads.
  • I have a mobile phone plan that works in 71 countries. If not, I will pick up a sim card (pay as you go) in that country if I stay for a considerable time.

What’s your favorite book and why?

I have two current favourites which are actually newly released: 

  • Happy Sexy Millionaire by Steven Bartlett. In this book, he talks about how we are polluting ourselves and our mindsets with social media and explains different ideas about happiness and how to create a positive mindset.
  • Working Hard, Hardly Working by Grace Beverly. Grace has put my mindset and worries into words and helped me to identify different productivity methods, routines, and self-care.

What small change has made a big difference in your life?

As a digital nomad and working freelance, I would often work way more hours than 40 per week, taking on more jobs than I could handle and spending 12 hours on a computer a day. 

I have recently given myself set times to work, write, or create content, and then specific times to go to the gym or explore a new place, and I try not to work too much on the weekends. When I visit a new place, I conduct research and find all the things I want to do and make time for them while still being flexible to say ‘yes’ to unexpected opportunities. 

Tell us about a deep passion of yours! What has your journey been like, and what advice/resources would you recommend for someone interested in learning more about this topic?

Anny Wooldridge water skiing with a large wave spray behind her

I am a competition water skier. I have been water skiing since I was young and have participated in slalom and tournament water ski competitions in England, the USA, and Colombia. 

How can people learn more about you and your work?

You can connect with me on Instagram @annysadventures on LinkedIn and Twitter. You can also visit my website, which has valuable articles about working abroad and Colombia. It also has my portfolio

 

Lauren Allain
Lauren is a freelance journalist from Seattle. She travels the globe in search of the best grocery stores, bouldering gyms, and snorkeling locations. Her mission at Freedom Is Everything is to help others make the transition into location-independent lifestyles.