My Digital Nomad Journey

I’m becoming a digital nomad – but I didn’t expect to feel like this

Some trips you take are just a holiday designed to unwind and reboot. But others are something more. They change something pivotal inside you. You come back home a different person. The changes might be so subtle no one even notices but you. Or they’re so glaringly obvious that you know it’s impossible to return to your life as it was.

When I returned from Indonesia, I came home with a plan to entirely reshape my life. I was finally going to start taking steps to live the life I’d always dreamed of – the life of a digital nomad.

campuhan ridge in ubud

Why a digital nomad – and why now?

In truth, I’d imagined for myself a digital nomad’s life of sorts well before “digital” work was even a concept. After my first overseas trip to Kenya as a 10 year old, I knew I was going to weave a lifestyle for myself that centred around seeing the world.

But the funny thing about dreams is that you can always find an excuse to not pursue them. My early 20s were defined by a cycle of working hard in Melbourne for a few months before buying a one-way ticket to new continents and staying there until I ran out of steam or money – whichever came first.

But those same years were plagued with an anxiety about how I could make this nomadic lifestyle more sustainable, maintaining the independence I had in travel while earning cash on the go. No overseas job – teaching, aid work, journalism – seemed the right fit.

It was after a big backpacking trip around Asia that I stumbled upon a Melbourne-based job opportunity that was never meant to be anything more than a quick way to save up for my next escape.

But it turned out the job – content writing for a digital marketing agency – suited my personality and my skills. Not to mention that my colleagues were awesome.

Still, uncommitted to the job in the beginning, I told my bosses travel came before anything else. And I guess they liked me, because they agreed to let me take off for ridiculous periods of time to appease my adventurous spirit.

When you finally realise the “perfect” life might not be your perfect life

It was the perfect setup, right? I could work the part-time hours I wanted when in Melbourne, devoting the rest of my time to blogging and novel-writing, and then take off for weeks or months during winter to escape the cold.

I felt liberated during those travel months. But those long 9-10 months in between made me feel claustrophobic. Endless, repetitive days shuttling between work and home. Hours spent in an office, barely glimpsing the sun or breathing fresh air. Days book-ended by a 3-hour return commute. The zombie shuffle with other 9-5 workers between platforms. It just didn’t feel right for me.

And for years, I battled with myself, knowing I had a unique situation, yet not the one I wanted. I was so loyal to my colleagues that I felt guilty disappearing for months on end. And during every trip, I resented having a deadline for my return. I wanted the ability to take off whenever I wanted, and the freedom to stay away as long as I could.

So instead, I waited for a catalyst – a change in bosses, or living circumstances, or love life – something that might just spur on the change I so desperately longed for.

And then Bali happened.

I recently travelled to Ubud in an attempt to settle down quietly away from the distractions of Melbourne and finish a novel. I thought I’d walk away from the trip with a completed manuscript. Instead, I found so much more.

Inspiring people who lived off a laptop and out of a suitcase. Open-air co-working spaces designed for digital nomads. The ease with which people were able to communicate with foreign brick-and-mortar offices.

And I realised three things:

  • There was no reason I couldn’t be one of these people.
  • If I really wanted a different life, it was up to me to pursue it.
  • I didn’t want to ever wonder “what if”.

My first step to becoming location independent

Now that I’d had this epiphany, I wanted that remote work situation to begin as soon as possible. So on my first week back in my Melbourne office, I arranged a meeting with my boss.

Maybe I was nervous. But I was so determined to begin my nomadic lifestyle right away that I knew I was going to achieve it, whatever the outcome of this meeting.

When we sat down, I stated my case. I was loyal to the company. I wanted to keep working for them. But pursuing this lifestyle was more important. Was there any way I could continue working for them remotely?

It was an immediate yes.

Cheers to that.

digital nomad amanda bensted

Is he the best boss ever or what? Honestly, I think his attitude was simply “we knew this day would come”. But it came with a warning too – my position may have to change, and my part-time workload could decrease even further.

I took it. I had already brain-stormed some ways to develop a supplementary income. Maybe I could freelance editing and writing services to other companies. Maybe I could finally monetise my blog, or crack into the paid travel writing biz. Certainly, I could publish a travel memoir (yes, this is a work in progress!).

Or perhaps, just maybe, I could find cheaper destinations that could allow me to sustain my reduced income lifestyle. That is all yet to be seen (and documented here, of course).

Anyway, a few weeks later, we trialled a “remote” work week, with me working from my kitchen table and communicating with my colleagues online.

As a digital marketing firm, this was fairly easy. We used Slack for instant communications, though I encouraged my colleagues to operate as if I were in a time zone incompatible with Melbourne’s 9-5 office life.

And in fact, I relished that week. I worked my own hours – generally 5 hours a day, broken up with walks along the beach, coffee catch ups with friends, and healthy lunch breaks. My days seemed more complete and fulfilling.

I usually began work before my colleagues arrived in the office, and I worked per project, not per hours. I found myself to be more engaged in what I was doing.

Even better, when I got back into the office, everyone supported me and stated their willingness to do what it took to make my digital nomad dream work.

What I didn’t expect from this outcome

With everything moving along at a rapid pace, what was my over-riding feeling?


Yep. Once I was told the life I dreamed for myself would soon become a reality, I felt sick in the pit of my stomach. It’s still there, a fear that I might not be able to sustain myself on my income, that I might miss family and friends and their important milestones too much, that I might not find remote-work-worthy destinations.

I’m becoming a solo, part-time, location independent worker. And that means I’m opting for a life of insecurity. Instability. Unpredictability. Unfamiliarity. A hand-to-mouth existence. A life of quick intimacies and just as sudden goodbyes.

All these things scare me to death. But they’re mainstays in a traveller’s life. And they’re what make me a better, stronger person.

And if it all goes to hell?

Then it would have all been worth it anyway, to rid myself of any future regrets.

My future is a gaping hole, a big blank canvas. And I’m inviting you to join me on the journey into the unknown. On this blog, I’m going to document my journey into digital nomadism and who knows, with you readers by my side, maybe it will all feel a little less daunting. 🙂


  • Reply
    Joshua Hoare
    August 15, 2017 at 5:17 pm

    Wonderful AJ,

    You are incredible and inspiring!
    Best wishes for your travels.

    • Reply
      Amanda Bensted
      August 17, 2017 at 6:01 pm

      Aw thank you Josh! Looking forward to what delights the world has to offer next 🙂

  • Reply
    August 15, 2017 at 5:16 pm

    I love this post so much AJ!!!! I want to hear all about the amazing life your living as a digital nomad as well as the perils and fears of the unknown!!
    Can’t wait to read more of your journey of becoming FULLY location independent!
    Congratulations girl!!!

    • Reply
      Amanda Bensted
      August 17, 2017 at 6:01 pm

      Thanks Judy 🙂 It’s thanks to all the encouragement from people like you that’s finally brought me to this point!

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