How I Screwed the Cubicle


This Monday, I was asked to share my story at Dojo Bali, as part of their monthly Lady Boss event. ‘How I screwed the cubicle,’ the theme read and I was one of three boss women sharing their stories of how the hell we ended up in Bali.

Captured at Dojo Bali during my talk.

Captured at Dojo Bali during my talk.

Now, you get a little used to telling that part of your story. The usual repertoire as you meet people around here is telling each other where you’re from or what brought you to Bali. And as usual, you get good at compressing your whole life story into a maximum of two sentences:

I was working in social media agencies for years but was burnt out and decided to travel the world while freelancing remotely. And here I am.

Seems simple enough, right? Pedestrian, even. The poor millennial girl couldn’t hack it in the cut-throat world of corporate life and fucked off to the island paradise of Bali.


But, in truth, this has been anything but easy and I’m not sure if I’ve truly left the cubicle behind yet.


The thing is: it’s hard to completely shake off everything we' know. We have been preconditioned to respect the linear path we’re supposed to follow. And I’d happily resigned myself to following that path and probably thriving in it. I wasn’t ever supposed to be the girl that was disruptive or different. I played by the book and I put my head and just got shit done.

But getting even a taste of something a little different slowly undid the ties of convention. Every crazy entrepreneur success story strikes that weird part of your brain about whether that could be you. Every influencer who’s making their money travelling the world starts ticking away at your imagination. Every opportunity to join them too seems a little less hard to just apply for.


I can’t exactly pinpoint the moment I thought that that girl could be me - maybe because I still can’t quite believe it.


I know the triggers. There was the trip to Vietnam - one of the first times I had let my inhibitions truly go and embrace the crazy, impulsive side that tends to spill out when I travel. I remember putting that thought out there: why not me? I could live and work on this island for a couple months and put my life on hold, right?

Travel Tiff - captured on the Vietnam trip that started this whole thought.

Travel Tiff - captured on the Vietnam trip that started this whole thought.


I told a friend, half believing this was another one of those crazy ideas that I would never follow through, half realising this was setting a fire in my heart that i hadn’t had before.

I’ll eternally be grateful for Viv for recognising that flutter too and holding me accountable. It took me just putting the thought out there and another to acknowledge it for things to start manifesting. From there, it just seemed to fall into place.

In my mind, I was going to wait until September so that i had at least made it to a year at my new job. But as my deadline came closer, it seemed less and less likely. I’d just push it back a month, maybe two, till it was a better time.

But there was never going to be a good time. And by that point, this thought, this possibility had started to manifest in my mind and I couldn’t shake it off. When the Nomad MBA eventually came around and I was compelled to leave on a tight deadline , there was no turning back.


Because the thing is, a thought like this cannot be unthought.


I’ve felt grateful for the people who’ve reached out to me over the past year wanting advice about their own doubts and thoughts of leaving. And frankly, the answer is the same. If you’re thinking about it already, that thought is likely never going away, and only going to compound. And if you’re at the stage to ask me about it, you already know what the answer you want is, because you know I’ll say just do it.

And while I’ve gotten good at taking that leap off the deep end, learning to fly has been a different story. I’ve fallen in love the discomfort of making myself thrive in a completely new place because of one, stupid ‘fuck-it’ decision.

But I was merely faking it till I would hopefully make it. I barely knew what I was doing and doubted myself at every turn. I thought about quitting constantly and I’m still a little surprised that I am still here. And it wasn’t until I eventually caved and went back to Sydney, and my old job, that I realised why.


The first time I left was all about escaping.


While I was eventually shortsighted to think of it as merely a sabbatical, the reasons behind my initial escape were clear. I was burnt out, stuck in a cycle of negativity and could find no escape except for a complete detox and fresh start.

Sure, I was able to discover so much more out there. I realised the potential I had to actually be a digital nomad, to actually thrive away from home. I learned more about myself that I had ever dreamed possible. And this was all even within the first month.

I loved all the perks - from the beachside offices to the spontaneous adventures and all the glamour of this lifestyle. As much as I wanted to be real about the difficulties of such a lifestyle, I was still in awe that it was even a part of my reality. The things that this life was not - monotonous, expected, corporate - were driving me more than the things that this life was.


And returning back to my old life - even for just three months - made me realise that this wasn’t just about running away, but something I was running towards.


Now, for me, this lifestyle is more about making it, then faking it. I still barely know what I’m doing but I know that this is what I have to be doing. I am gaining so much more, not just avoiding the negative things of my previous life. I feel alive, in control and excited for anything else to come.

The face of somehow who’s happy with the choices who’s brought her to this point.

The face of somehow who’s happy with the choices who’s brought her to this point.


I’m not running away any more. The cubicle no longer seems like a backup plan or safety net. It feels like chains that keep me from truly accepting a new way of thinking about work and life. It’s holding onto the person of the past who had not had this thought nor seen what it could manifest.

So how did I screw the cubicle? Well it’s taken me two years and countless doubts, setbacks and temptations but I’ve finally cut the ties. There’s no turning back now.