I was up before the sun on a bleak Winter’s day. The wind was so strong it bent gum trees in half and whipped the rain in sideways. Rain so cold and fast it felt like splinters of ice pricking my cheeks as I struggled to my car to begin the daily ritual:

Phone Charger: Check

Full tank of Petrol: Check

Clean Car: Negative

The floor on the passenger’s side was coated in a dry red dust from the boots of a miner I had taken home after a long stint in the Pilbara. I reached beneath my seat where I kept my best friend, my hand vacuum. It was a birthday present from a mate who found my new career hilarious. It came with a note, “Gotta keep the stars up!” in reference to an Uber drivers rating out of five stars. Midway through removing the Simpson Desert from my car I received a text from my Mum. I thought it strange she was up so early. The text read:

“Time to get a real job please. Not safe out there!”

Beneath the text were five links to vacancies on the online job board Seek. I smiled, shook my head and closed the message without opening the links. I had a real job. Taxi drivers aren’t questioned on the legitimacy of their profession, so why am I?

It turns out my mum was woken from her slumber by a terrible nightmare. I had been kidnapped, killed and stuffed in the boot of my car by a rogue passenger. “You just don’t know who is getting in your car!” she protested later that morning.

I wasn’t annoyed by her opinion on how safe I was driving for Uber. You would need to be the world’s dumbest criminal to commit an offence in an Uber. (A) You are being geo-tracked (B) An electronic record is being kept of your movements. Apparently, Uber passengers are the ones at risk, with AM shock jock Ray Hadley declaring, “your next driver could be Ivan Milat.” Rather incredible claims that Australia’s most notorious backpacker killer could be moonlighting as an Uber driver while imprisoned at Goulburn Supermax. Crazy stuff Ray!

I was, however, slightly incensed by her dire opinion of my current employment. Mum wasn’t the first person to cast a judging eye over my current lack of “career prospects”. The inevitable small talk question of, “So what are you doing with yourself these days?” had plagued me since I started driving for Uber. My response of, “I’m driving for Uber,” would be met with, “yeah but what else are you doing?” followed by a shrug of the shoulders, a “fair enough” and a roll of the eyes. It made me think, what is considered a legitimate job in Sydney?

At times, Sydney is a living, breathing stereotype. Here is a list of the professions of my passengers on this day:

6:30am: Madison – Bondi: Yoga Instructor

7:15am: Daniel – Coogee: Digital Media Account Manager

7:50am: Lloyd – Vaucluse: Financial Services Consultant

8:15am: Dariah – Balmain: Artistic Director, Film

Most would agree, a very impressive list of professions. So far, one particular group has been grossly underrepresented by my online diary. Where are all of the people from the Sutherland Shire? I asked my passengers what they think people from the Sutherland Shire do for a crust:

Madison: “Surf instructors and tradies…. yeah heaps of tradies in utes.”

Daniel: “Mainly hairdressers I reckon.”

Lloyd: “oooh who was that guy from that show The Shire? The rapper….. Riff Raff? haha heaps of rappers apparently.”

Dariah: “Probably tradies…. yeah plumbers, electricians and carpenters.”

I wasn’t satisfied by these answers. Until now I had avoided driving for Uber in The Shire. No it’s not because I don’t want dirty floors from tradies boots or aspiring rappers spitting me their next big hit, it’s simply because there hasn’t been a big enough demand down South to warrant an expedition. That all changed when I saw the Uber map light up in the deep South. It changed from green to crimson, to bright red, which means supply is building. Wish me luck.

Beep. Beep. Beep, Kelly – Como

Breathtaking. Acres of wild bushland kissed by glistening rivers, bays and inlets. Como was magnificent. No older than 25, Kelly emerged from a timber mansion on a hill overlooking the Georges River. She wore a floral, floor length dress, apparently called a maxi, which had a split down the left-hand side. Clutching a small black bag, apparently called a clutch, she crept precariously down the steep driveway on impossibly tall stilts, apparently called stilettos. She was gorgeous. Tanned with shoulder length auburn locks and teeth so white they sparkled as the sun caught them.

“Heyyyyyy! This is the first time I’ve used Uber in the shire!” Kelly exclaimed as she gracefully entered my car. “Just down to Northies in Cronulla thanks. Do you know where that is?” she asked politely.

We made our way toward Cronulla Beach and its most popular nightlife haunt, Northies. Kelly and I chatted away about Uber, shire life and whether John Snow would return in the next season of Game of Thrones. Kelly doesn’t rap, cut hair or fit downlights. She is an architect at one of Sydney’s leading construction firms. Kelly and I parted company on the corner of Kingsway and Elouera Road. I watched her disappear into the bustling crowd at the beachside bar.

Shire-folk don’t live up to their reputation. Not a single hairdresser, tradesman or rapper encountered in the eight hours I spent down South. Contrary to popular belief, people from this part of the world travel widely, although I wouldn’t blame them for never leaving. It really is a beautiful part of Sydney.

I was about to turn off my app after dropping a group of lads to the bushland suburb of Menai after a night out at a local club called Carmen’s. The boys thought it would be hilarious to pretend they were doing a runner, which is impossible using the Uber app. I wasn’t even annoyed they left all their doors open as they ran screaming down the street. Well played. As I walked around my car closing the doors my phone lit up once more. One last job and then home to bed I thought. Rule #1 of being an Uber driver. Never let your guard down, not for a second. My night was about to come alive.

Beep. Beep. Beep. Jack, 3 minutes

I pulled into Llanberis Drive in Menai. Towering brick and stone houses with perfectly manicured lawns filled one side of the street. Directly opposite was thick bush as far as the eye could see. I parked out the front of the address entered into the app and waited. It must have been about five minutes before I picked up my phone to call Jack. I had my windows down because the last group had been smokers. Even though they didn’t light up in the car, I could still smell the acrid tones of Winfield Blue hovering in my backseat. I went to call Jack but froze when I heard chaotic rusting from the wild bushland to my left.

I frantically activated my central locking, raised my electric windows and put my car into drive. What on earth is that!?

I could make out a large figure scrambling up the embankment and over the silver guardrail. Only when the beast met the glow of the streetlights did I realise it was a man. Shirtless, about 6ft 2” in his early twenties, with wiry, curly hair like a tuft of steel wool had been sewn into his scalp, the beast approached. He was wearing ripped, blue jeans and was missing a shoe which gave him a ghastly limp. He was carrying a wine bottle in his right hand, which he swigged with vigour. He made his way to the front of my car and gave me the “thumbs up” signal. Could this be Jack? I had never seen a smile so wide. The enormous whites of his eyes gave him a maniacal quality, compounded by the image of the man throwing his head back and chuckling like a kookaburra as he reached my car.

I lowered my window slightly and asked, “Is that you Jack?” Before Jack could open his mouth the furious screams of a man echoed down the driveway of the house Jack had entered into the app. High powered security lights turned night into day as the sound of an electronic garage door opening woke the neighbourhood dogs.

“Ha! Looks like we’re off here son!” said Jack casually as he opened my passengers side door and sat down. “Ahhh here he is! HA HA HA!” laughed Jack, pointing toward the house. An elderly Asian man wearing a dressing gown emerged from the garage. He was brandishing a metal rake and screamed, “Where the f#!k is he!” Jack reached across my lap, lowered my window and yelled back, “Oi! Close but no cigar champion! HA HA HA!” The man hurled the metal rake down the driveway at my car but came up short. I put my foot down and sped out of Llanberis Drive.

“HAHAHAHA! You little Bewddddy!” roared Jack as he slapped himself on the knee and took another generous gulp from his bottle of wine.

“Mate! What the hell happened back there?” I asked as my mind tried to digest the chaos. Jack went on to tell me a story that defied belief.

“HAHAHA! Where do I start? I have been knocking off this Chinese bird who lives in that prison. No joke, it’s a prison! Her old man is strict as, the c#!t has cameras everywhere! She had to sneak me into the house in the boot of her car. Anyway, I’d been out partying and had at least a bag and a half of whizz fizz up my snout before I even got there. I went to absolute town on this bird right, but I couldn’t finish! I The gear was that good I just couldn’t get one away. She fell asleep and I’m laying there with full blown hard on. I thought f#!k it, I’ll finish it myself. I crept downstairs to her family’s computer room to find a bit of inspiration. On my way, I passed this cabinet full of wine so I pinched one of the old man’s bottles of red. Anyway, after fifteen minutes of searching, I found a top video on RedTube and went to work. I was going hammer and tong for at least ten minutes when I was interrupted by her mum screaming. She was standing at the door watching me. I got up to run but tripped over my jeans which were around my ankles at the time. I managed to get one shoe on when I heard her old man thundering down the stairs, so I grabbed the wine and legged it out the front. I had to hide in the bush across the road and only just had enough batteries to order an Uber. Thank f#!k for Uber!”

I listened on, mouth gaping, to Jack’s tale of debauchery. “I’ll tell ya what! This isn’t a half bad drop!” Jack announced, offering me a swig from his bottle of wine. On closer inspection, Jack was drinking from a bottle of Penfold’s Grange, 1992. He had unknowingly pinched a bottle of $500 wine. “Must have been a good year!” He laughed as he polished off the rest of the bottle.

I dropped Jack home and immediately went offline. I sat in my car for five minutes wondering if other Uber drivers were coming across as many colourful characters as I have in my short time as a driver. I also spared a thought for the poor woman over in a house in Menai spraying her computer with disinfectant before deleting its search history.