3 Challenges Every Remote Worker Experiences

A lot of people have been coming up to us asking: “is it real, being a digital nomad, or is it all a hoax?”. We can’t blame them for thinking that. If we weren’t living this lifestyle every day, we might also think it sounds too good to be true. That’s why we wanted to let you hear it from the horse’s mouth! We’ve interviewed 3 experienced digital nomads, who’ve been doing this for years and we’ve put their stories into a handy e-guide for you to read through.


In the interviews, they share their personal experiences on:

  1. Hurdles they encountered when transitioning into the remote lifestyle, and how they’ve overcome them
  2. How they combat the “lonely” aspect of a remote lifestyle
  3. Their best advice for people who still need to take the leap
  4. Many other tips on getting the most out of being a digital nomad!


As a bonus chapter we’ve included our own experiences of being on the road full-time. Spoiler alert: we never want to go back to the regular schmegular office cubicle! So, do you want to know what it’s really like? The e-guide with full interviews is only available to people on our email subscribers list. Sign up at the bottom of the page here to receive your copy!

Nevertheless, we also wanted to offer you a little sneak peek in this week’s blog post. We’d hereby like to introduce you to Nathan, Dave, and Victor!


What were the 3 biggest hurdles you faced when transitioning to the remote lifestyle, and how did you overcome them?


Nathan Morgan


My name is Nathan, I’m 27 and from the UK. My remote working experience started in January 2014. I’m currently based in Chiang Mai and I run several successful online businesses. First and foremost, I’d say I’m in the SEO (search engine optimization: In Focus SEO) business in its various forms. Being able to rank websites on Google has allowed me to start a number of online ventures, some of these include drop shipping physical products, lead generation, client based SEO work and more recently branching out into private labeling Amazon FBA sales. Diversifying how I make money is key to me.


  1. Earning actual money to travel and live

Let’s not beat around the bush. This is the hardest part. Like they say though, ‘where there’s a will there’s a way’. I had a monthly figure of X in my mind before I’d travel and see the world. Yes, I could have done it with less. I could’ve started traveling on my savings and let the need to make money motivate me (both approaches have their positives), but I was a little more cautious and chose to build up my businesses before I took the leap.


  1. My own mentality

Anyone who tells you that it’s not hugely intimidating to do this, that it’s ‘easy’ to just uproot your life and pursue your dreams, has probably never done it. For me, overcoming this was about making the transition as easy as possible. I researched popular remote working locations and weighed up the pros and cons. I decided that I wanted it enough to put the fear aside and do it anyway. I’ve never looked back since!


  1. Discipline

When you get to a new and exciting place full of interesting people and opportunities, it’s far too easy to get caught up in bright lights of it all and forget how and why you’re really there. Sometimes you have to be able to say no to that salsa class/drinks/meals out with new friends and get down to business. After all it keeps the whole thing going!


Dave Weatherall


Hi, I’m Dave Weatherall, creator of That Travel Blog; a blog for travel-preneurs and those who aspire to be one! In April 2014, at the age of 20 without a degree and no savings, I quit my 9-to-5 desk job to travel indefinitely. With my blog, my main sources of income are from affiliate marketing, Instagram promotion and guest blogging. I also make money while travelling with my team of digital marketing nomads; That Social Agency.


  1. Entrepreneurial freedom

Being your own boss is incredible but it can be extremely stressful when you have no idea what you’re doing! I experienced this feeling almost 75% of the time while transitioning to the remote lifestyle and the other 25%, I only thought I knew what I was doing! There’s no-one there to tell you what to do next, so you just have to go figure it out for yourself.

I continue to overcome this by seeking feedback and advice at every opportunity! Even if you run out of friends and family to annoy, there are countless amounts of people on the Internet who are ready and willing to critique you and your work. Just remember to not take everything to heart.


  1. WWW (Workspaces With Wi-Fi)

When you’re not tied down to an office-space, it is easy to waste a lot of time trying to discover exciting Wi-Fi cafes, e.g. cafes with power sockets, a chilled environment, non-pushy staff, and reasonably priced food and drinks.

I avoid spending too much time walking around by paying a little extra for a nicer hotel or Airbnb, with super-fast Wi-Fi and a space for my work. That way, I can cross out most of my to-dos while I am at home and save money on endless coffee, for exploring when I’m on a break.


  1. Saying goodbye to family & friends

I have been travelling on and off for almost 3 years. I miss my family and long-lasting friendships. I have 2 brothers who I rarely see which makes me especially sad.

But I also love constantly meeting new people and hearing unique stories. While I am young, I want to soak up as much ‘new’ as possible. This does mean saying goodbye to many meaningful relationships but it’s a worthwhile sacrifice (for the moment). Luckily, you can always decide to travel home for a bit. There’s no one telling you that you can’t!


Victor Kung


Hi there, I’m Victor Kung. I started living the remote lifestyle in February 2016 when I quit my high-paying consulting job at Accenture. I run a small web agency with my sister called Tandem Designs. On the side, I created a blog called The Remote Lifestyle, which chronicles my transition from a corporate 9-to-5 to living and working remotely.


  1. Giving myself enough financial runway
  2. Preparing everything I needed for my web agency
  3. Taking the leap


The first two are kind of related. Before I quit my job, I made sure that I had everything set up for my web agency, including:

– Website

– First set of clients

– Contract templates

– Incorporation

I also waited until I had enough projects to cover me for the next 3 months. To be honest, these things weren’t difficult. It was more about executing the game plan and going through my checklist.

The most difficult part was actually taking the leap. I had talked to family and friends about this already, so I was mentally prepared. However, actually speaking with my manager at work about this was a nerve-wracking experience.

Luckily for me, I’ve found everyone, including my colleagues at work, to be incredibly supportive. And that made it so much easier for me.



The Remote Trip

Share your thoughts