Going on holidays in the gig economy

As I plunged into my breakfast, breathless at the divine threesome that is crème fraîche, avocado and poached eggs, I nursed a growing anxiety about meeting that day’s deadline. My dreadful hangover wasn’t helping, and on any other day, this would be a fairly normal state for me.

But I wasn’t working from home like I usually do in Singapore. I was at a café in Melbourne, where I was supposed to be on holiday. Next to me sat my quietly fuming partner, who was picking at her fried chicken and waffles after being told that I would not be accompanying her to the State Library of Victoria – because I had to catch up on work.

Across the road, at a trendy café sporting whitewashed walls and canary yellow chairs, an impossible queue snaked out of and up the cobblestoned alley. This was the heart of winter, but we were warm, comfortable and fed. All the same, we were miserable.

We were three days into a weeklong trip, and every day so far had devolved into the same mundane routine. We’d sleep in a little, then I’d work on a story before we headed out for a late breakfast. After some sightseeing, we’d settle into one of Melbourne’s many coffee shops where I would work some more. Dinner was always followed by one too many drinks, and by the third day, I was struggling to meet deadlines.

When I finally reached the peak, I pulled my phone out to find an 800-word angry email in response to a story I’d recently published. Reading it from my perch looking out across the city skyline, I experienced a poignant combination of relief and amusement

Such is the life of a freelance writer – every vacation ultimately devolves into a working holiday.

I’m not alone in this. The rise of the gig economy has made freelancing an increasingly popular alternative to more structured “corporate” jobs. There are the obvious reasons for this – some people desire more flexibility, while others refuse to be constrained to a stuffy cubicle in a nondescript office. For those in a creative field, there’s also the potential to make more money than if you were to work full-time for a single company. And there are the little things: going shopping on weekday mornings sans the weekend crush, taking post-lunch naps, heading out on trips anywhere, anytime – as long as you deliver on deadlines.

But what often goes unexamined is the toll a freelance lifestyle can take on both you and those close to you – specifically, the lack of a structured schedule and demarcation between work and everything else. Ultimately, being a freelancer is only truly ideal when you’re single and have no friends. I might have accepted that my days will be punctuated by work regardless of where I am, but this is not normal for most – and it’s selfish and unfair to inflict on other people the fickle irregularity of my freelancer’s life.

Several months later, I found myself on a solo jaunt in Hong Kong. I had just consumed a huge dim sum breakfast somewhere in the hilly region of Tai Po, where laundry lines decorate low-rise houses in a village still largely untouched by urban development. This was followed by a hike, and as I was trekking up a particularly challenging flight of stone steps, my phone buzzed in my pocket.

In an effort to leave work behind for this trip, I had opted – for the first time in four years – not to bring my Macbook Air along. “Whatever it is, it can’t be that important,” I thought. When I finally reached the peak, I pulled my phone out to find an 800-word angry email in response to a story I’d recently published. Reading it from my perch looking out across the city skyline, I experienced a poignant combination of relief and amusement.

Surveying the vast density of Hong Kong’s urban landscape, I made an elevated decision. “I don’t have to deal with this right now.”

What a feeling it was as I shoved my phone back into my pocket, proceeding to forget all about that email. Happily, I walked on.