6 Challenges of a Working Digital Nomad

6 challenges of a working digital nomad via Birds of a Feather Press. Advice for travel bloggers working on the road.
Kelly Sheldrick
Kelly Sheldrick

Columnist: Kelly Sheldrick from Cycle Trekkers


I love working on the road as a digital nomad … most of the time. It definitely has a lot of positives. Working where and when I want, being my own boss and being able to fulfil my travelling dreams are definitely a few of them; however, just like with any job it still has challenges, and here are six I’ve experienced during my cycle trekker adventures:

1. Finding a reliable internet connection

WiFi is definitely becoming more widely available, however it is still something to be mindful of. Even while cycling through Canada, I found finding regular internet access a bit of a challenge.

2. Being self-motivated

Self-motivation is critical to working on the road. Unlike a job that has set hours, working on the road requires you to work when you can, as opposed to when you want to. It’s easy to get distracted by events going on in the new city you’re visiting, or to find the motivation after a long day of travelling.

3. Finding a quiet place to work

This can be a major issue – one that I’m currently experiencing as I write this post.

4. Travelling with a laptop or tablet can be a pain!

Working on the road means carrying extra equipment, with that comes additional insurance cover, extra weight and extra valuables to worry about, as well as more breakables.

5. Being organised while living an unconventional life

Living on the road can be a bit chaotic – delayed flights, dodgy hotels, missed buses, “Bali Belly”, sudden change in travel plan. All these things occasionally happen and can put a bit of a kink in your digital nomad lifestyle. This is why it’s important to embrace an organised, but flexible and chaotic lifestyle.

6. Working online can become lonely!

There is definitely a risk of becoming isolated, and a little bit lonely when your job just involves you, your laptop and the digital world.

Over the coming weeks we’ll look at each of these challenges, and Jay and I will share some tips and advice about how we overcome them.

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Kelly Sheldrick

Kelly Sheldrick Bio

Kelly is The Nomadic Times contributor here on Birds of a Feather Press. She’s a a digital nomad currently cycling around the world. She has visited over 20 countries by bike and over 65 countries in total, 10 of which she has worked in. Kelly funds her travels through a combination of digital nomad work, which includes travel writing and blogging on her website Cycle Trekkers (www.cycletrekkers.com), teaching English (both online and in person) and picking up the odd seasonal or casual job along her travels.

She has written two ebooks about her adventures, which are both available for purchase on Amazon: Cycling Canada: Coast to Coast Trip Notes and France to China by bike.

Visit Kelly’s Author Bio page to connect with her on Social Media.


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Author: Jay Artale

Focused on helping travel bloggers and writers achieve their self-publishing goals. Owner of Birds of a Feather Press. Travel Writer. Nonfiction Author. Project Manager Specialising in Content Marketing and Social Media Strategy.

2 thoughts on “6 Challenges of a Working Digital Nomad

  1. One of the major pains of working on the road is finding great internet speed, which has been a problem for me for the past couple of months in Latin America. Even the speed in Mexico City, where I am currently based, is a quarter or half the speed in Europe/US/Asia.

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