Working as a digital nomad

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

I’ve read so many blogs that say nonchalantly – hey quit your job and become a digital nomad. As though it’s super easy to find work online.

If you are like me and don’t have a technical skill (like coding, design etc), this world can feel totally out of reach.

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

Monkey - shown the plate now I want more







Here’s my journey so far.

I left my job in the UK – December 2016

After 5 years of working in London advertising agencies, I was burnt out. I was working 12 hour days (with no overtime pay), with loads of stress and abuse from clients that made me cry in the toilets. Spontaneously, I decided to go away & have a break.

I wanted to do something productive while traveling

I didn’t want to bum around traveling, so I decided to learn Spanish. But if you’re not a natural linguist like me, it takes a lot of effort and is expensive. 

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. (If you need tips on how to cope in a similar situation, click here)

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. I ended up living with him and his Portuguese designer friend for a week. They opened up my eyes to the world of remote work. Australia was a screen writer and Portugal was a UX designer.

However, I still didn’t believe that I could join this world. I’m not a UX designer, app developer, etc. My background in account management gave me client-relationship building skills but I didn’t think this gave me skills to work remotely. So when I found a workaway job advertised in a boutique guesthouse in Cartagena, I booked a flight immediately to go there.

I worked in a hotel in Cartagena. It was awful.

8 hour shifts, and I was micro-managed, patronised and generally treated like “mierda”. 💩.

However, I didn’t have any other options at the time, and ended up working here for 2 months, while I got my life back on track. I got a new passport sent here from the UK, took Spanish lessons every day and had free accommodation.

Lucky break number 2. One of the guests in the hotel worked as a virtual assistant and transcriber. She was paid in dollars and could work anywhere – i.e. from the pool in the hotel. This started to put things into perspective; I was working for free in a stressful hotel for 8 hours a day. 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 as fuck.

I know I was very flukey, as the company had just won a new client so they had a lot of work. But it also made me realise, if you don’t ask, you don’t get.

Yes it was boring but it provided me with constant work for about 6 weeks. Anything from 4-8 hours a day, at my set rate of $20 per hour – working my cafes or sometimes even my bed, I couldn’t quite believe how easy it was. 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 that 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


I’m not going to lie – I felt pretty intimidated by Upwork. The amount of jobs is great, but blimey there’s a lot of competition for every role. I applied for virtual assistant and transcription roles.

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

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 Upwork 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.

If you want to follow my journey and learn some tips along the way, click here.


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  1. I can’t wait to learn more about your journey!

  2. 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)

    • hats

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

  3. 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 🙂

  4. 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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