My quest to become a digital nomad – I’ve been shown the plate, now I want to eat it

Want to become a digital nomad? Read lots of ‘inspirational’ blog posts, encouraging you to ‘just quit your job’ and start working online? Feeling overwhelmed about where to start?

I’ve certainly been there. With a degree in English Literature and experience working in account management, I’ve learnt soft skills but there’s no one thing.

When I left the UK 6 months ago, I didn’t know this world existed. Since then, I’ve been shown the menu, had a bite of an entree. And now I’m hungry for the main course.


How to become a digital nomad - monkey eating banana

Here’s my journey so far.

I left my job in the UK – December 2016

After 5 years of working in London ad agencies, I was burnt out. Constant 12 hour days, with abuse coming right at me, from every angle, that made me feel like a human punch bag. One day, it got too much. On a whim, I booked a flight to South America.

I wanted to do something productive

I didn’t want to bum around travelling, so I decided to learn Spanish. But if you’re not a natural linguist like me, it takes a LOT of effort & is expensive if you take lessons. 

So I set off, nervous but excited, off on my trip that began in Guatemala. Day 1 my bag was stolen which included my passport, phone, money, bank cards and ID.

I refused to let this ruin my trip; I couldn’t go home on day 2. But it did cost me a lot.

I arrived in Medellin. I had no idea what to do.

As I couldn’t work in the country without a visa, I thought I had only one option if I didn’t want to spend a load of money living here:

  • Get a job on (the website that offers accommodation in exchange for some work)

Lucky break number 1. I started chatting to a random Aussie in a cafe. He had a spare room in his house, and  I was looking for a house… so I moved in. Without realising, I’d just moved into a nomad house.  Australia was a screen writer and our other housemate, Portugal, was a UX designer.

They opened up my eyes to this world of business communication via Slack, Skype & Upwork – but I didn’t believe that I could join this world. I’m not a UX designer, app developer. What would I do?

So when I was offered a workaway job in a small hotel in Cartagena, I went.

I worked in a hotel. It was awful.

8 hour shifts, every day. All the workers shouted at me using Cartagenan slang. I had no idea what I was doing, and was treated like total mierda. 💩.

But I didn’t think I had any other options, so ended up slaving away, miserably, here for 2 months – until my new passport arrived.

Lucky break number 2. One of the guests in the hotel worked as a virtual assistant and transcriber. She explained how she could work anywhere she wanted – just before she started tapping away by the hotel pool. This put things into perspective; I was working for free in a stressful hotel for 8 hours a day. She was making more money in one hour than I was in a whole week.

Plus, I was already lukewarm to the idea of remote work from my Medellin friends, Australia & Portugal.

So I asked her if they needed any more workers, sent her my CV, and pretty instantly…

I was hired! My first remote job!

I started transcribing interviews with people in the American navy. Random AF.

It was flukey. The company had just won a new client so instantly they had a lot of work. But I realised – if you don’t ask, you don’t get.

Yes it was boring but it provided me with constant work for about 6 weeks. 4-8 hours a day, at a rate of $20 per hour – working from cafes or sometimes even my bed, it was almost too easy. And how relaxing! It funded my trip to Providencia, my exploration in Medellin coffee and views, and more. I’d had a small taste of the remote working life…

And then the project ended.

I didn’t want to go back to the days of working in a hotel, for bosses that shouted at me, or clients that treated me like pants. I was desperate to keep the flexibility of being able to work in my favourite cafe at whatever time of the day took my fancy.

So I looked online to see what else I could do and I found Upwork, the world’s largest online workplace.

The Upwork journey begins

 How to become a digital nomad

I felt pretty intimidated by Upwork. The amount of jobs is great, but blimey, I had no idea how much competition there would be for every role. With my transcription experience, I applied for virtual assistant and transcription roles.

With no reviews, it was hard to bank my first job. However, I relentlessly kept on searching and applying. Finally, I found someone who wanted his grandma’s handwritten diary transcribed. I applied with a personalised cover letter pointing out minor grammar mistakes in her diary, and…

Lucky break number 3

I was hired AGAIN!

It took about 6 hours and I only earnt $30, but I didn’t care; I was off. I got a glowing 5* review so surely, they were all going to flood in now. Again, I was wrong.

And I’m unemployed again.

So I apply for more jobs… so far I have applied for at least 20, have got through to the interview process of a few, and have dodged some scams too.

To follow my journey and see if I succeed in the journey, click here.


  1. Pretty cool story and scary at the same time, keep the good work because at the end the only way to know it’s by trying ! And may try to do the same in the future ( travel)

    1. Thank you! And exactly – I’m refusing to be defeated!! It’s tough but a hustle which hopefully will pay off 🙂

  2. Ups and downs as we go) If you like a life to be as a roller-coaster ride, then be a freelancer, at least, starting as a new one is always a good idea 🙂

  3. I too am on a journey to find a new career and hope that being a digital nomad is part of that. Thanks for sharing, it is great to be able to read about some of the difficulties not just the glossy brochures selling you the easy life. I look forward to sharing more of your journey

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