Dispatches From The Road: A Survivor’s Guide To Sydney

It’s a little endearing when everyone you know in Sydney keeps telling you how Sydney hates you and wants you to die.

The resume of dangerous places you’ve been to and survived doesn’t count for anything here. It doesn’t matter if you’ve ever taken a stroll through the Tenderloin or moved through areas of New York where people casually talk about the time some guys with guns broke into their apartment and stripped their housemates naked and left them bound and gagged for hours. It’s all meaningless.

“Don’t get mugged,” your friends still tell you.

“You’re not from here. These people can smell it,” they say and then they give you the finger as they drive away while you will smile at the thought they are at least looking out for you.

Dear Family…

Sydney is Australia’s New York. It’s big and busy, so it’s big city rules here. People aren’t nice because they don’t have to be. It is fast and constantly moving and if you are not paying attention, you will miss everything.

That is your first lesson. Sydney is all about the little details, so keep your eyes open. The next is that you’re staying at a hostel in the Central Business District (CBD), it’s probably going to be a dive. Embrace the grit. You’ll be attracted to the cheap prices of an 18-person dorm, but you will quickly find backpackers from the British Isles have taken over and formed their own little clique. These are the kind of people who are working for a few months to afford a ticket back home and have seen hundreds of people pass through here. Now they have ice in the veins.

Which makes life somewhat more difficult. There is nothing more terrifying than a horde of British backpackers at the best of times. They are a bloody thirsty people with a habit of travelling in packs and colonising hostel dorms like Britain still owned the world and they were setting up the Raj. Soon the place smells of wet towel and they are smuggling in goon for pre-drinks before heading out into the Friday and Saturday night Sydney carnage.

But it’s okay. That is why you will be spending as little time in your hostel as possible.

Here I am in Sydney…

Once you come to this realisation, you will need to find stuff to do with no money in a place where everybody looks at you and instantly sees dollar signs. From transport to hostels to food, everything is set up to get you to consume and to consume costs money. You are here primarily to stimulate the local economy. That’s what travel’s about and it’s worse when you turn up in a big city.

Seeing some cool stuff…

So make your money last. If something’s FREE, take it. If it’s discounted, exploit it. If you can, scam it. Nicely. Art Galleries and public art festivals like Vivid in Circular Quay want to be your friend. Let them. Wait until some people in a cafe get up before sitting at their table to make it look like you bought coffee. Do not be fooled by the $10 cafe breakfast deals. Buying yoghurt and a banana from Coles or Woolworths and liberating cutlery from Starbucks is cheaper. Learn how to hang out in public space without getting arrested for loitering. Make friends, they will show you things you never knew existed. Do anything except go back to the hostel before 11pm where you will have to deal with the Brits in your dorm.

That’s the end of lesson two. Lesson three is that being broke sometimes means putting your morals second. This is particularly important if you’re from San Francisco. Ignore whatever ethical problems you might have with supporting a duopoloy that controls 80 percent of the domestic Australian grocery market. Dropping $30 in groceries from Coles or Woolworths is going to be cheaper than paying $20 a night for dinner.

The fourth lesson is that most people in Sydney really do hate the place. They’re unsatisfied with what they have. It doesn’t matter how much cool stuff you find or how much you love the city, everyone’s gonna be an asshole. Everyone assumes the worst. There’s too much traffic. Too many people. Everything’s too far away. People are mean.

And in some ways they are right. If Sydney were a person, it would be a 40-year-old, divorced white man in a $3000 tailored suit who does Krav Maga every day after lunch as part of a company initiative he introduced to teach confidence at the negotiating table. He is fun to drink with, so long as he is buying the drinks. Just never forget that from the moment you met, he has been trying to screw you.

You must temper the cynicism by looking around you. At its best, even a single day in Sydney feels like living in a Cat Empire music video. It costs nothing to chill out on the Opera House steps and watch the world go by. Summer feels like one long party and even in Winter, there are days when the air is warm and the sky is endless and blue and just sitting on a park bench or being taken for a drive through the suburbs feels like it belongs on a postcard. The kind you send back home with the word “jealous” scrawled on the back in capital letters and the question mark heavily double emphasised.

And just casually hanging out…

That being said, you still have to deal with the people. You will get bad service in cafes for not wearing a suit, but the moment you put on a shirt people in the street will start trying to bum change. Getting into some bars means being paddled by the Security Guy whose aggression level is more extreme than the combined brutality of every name on the LAX security-staff payroll.

In order to cope, you will need to leave the CBD. Which is necessary anyway, as there is more to Sydney than the cluster of skyscrapers downtown. It is big enough for its own neighbourhoods with their own unique character, even if this is Australia and the country hasn’t been around long enough for anyone here to really get to grips with what this means.

Newtown and Enmore should always be your priority. Mostly for the counter cultural vibe. These are areas where godless Marxists paste up newspaper adverts for their newspapers, radical feminists travel in packs, Mexican restaurants seem to be a thing and dudes sit outside bars wearing tattoo sleeves down to their wrists. Good people.

But that isn’t you’re only choice. There is Bondi, a playground for rich kids where the uniform is all skin. Bikinis, bare chests and board shorts are everywhere. Wetsuits turn up in the cold. It is also quintessentially Australian and every year thousands of tourists bus over in summer to almost drown after getting caught in a rip-current. Life or death, the main thing is that beaches are free and Sydney is all about its beaches.

Darlinghurst is home to the city’s Madi Gras and Crown Street down by Central Station has its own vibe. Then there’s Glebe. Which is interesting in that it’s basically a metaphor for Sydney itself: it comes in two halves. You know you’ve moved from The Other Glebe to the Yuppie Glebe when you walk down Glebe Point Road and stop seeing people drinking cans of Jim Beam around 10am and start seeing Jaguars parked out the front of multi-million dollar Victorian manors.

In the end, the core skill is knowing how, or where, to recognise a friendly. Find them in places like the Gertrude and Alice bookstore cafe in Bondi where the staff are chatty and will smile and talk to you even as you slur your way through the conversation because the mattress you slept on last night is what they also use at Gitmo when waterboarding or electric shock no longer has an effect. If the sleep deprivation is too great, probably just stick to reading.

Found this bookstore…

Otherwise there’s Sedition barbershop, run by the Anarchist barber of Darlinghurst. When you visit, remember to pay attention to the details. Notice the wall of cock on your right as you walk in and the bust of Lenin draped in an Orthodox cross on a shelf. The place is run by Michael Joyce, artist, pacifist and Anarchist. Today’s newspaper will be open on his table and he will talk to you about it. Be ready. He is all class war, but the conversation that follows will be worth the $30 cash you hand over for that haircut. If you can’t afford it, pick up a six-pack instead, introduce yourself and hang out for an afternoon. Michael Joyce will appreciate it and what you will get from that time will be priceless.

Met this guy…

Whatever you do, pretty soon the walls are going to close in. You can’t run forever. At some point you will need to plunge back into the heart of the city and when you do, you will feel the anger and resentment boiling up. Your natural instinct in this moment will be to turn the anger outwards, into pure, unfiltered rage where you shred the next person who so much as brushes past you on the street. This is wrong. Sydney will push you to your limits, but do not give in. You are better than that. Act accordingly.

Do not, for instance, respond to getting bad service in a cafe by heading back to where you are staying and putting on whatever outfit makes you look like you might be carrying a switchblade just for funsies. Then, absolutely do not walk back up George Street in the direction of the business district to find the Glitziest, suitiest cafe where you might sit down at a table both in sight of the register and next to any group who looks like they’re living in MadMen. Do not order a coffee and take your time reading a newspaper, all the while remaining keenly aware the serving staff are terrified of you and are looking for any reason to press the silent alarm under the counter.

Likewise, it is wrong to encourage your bad habit of introducing yourself to people as Vice Magazine Australia’s editor Royce Akers, by upping the stakes and introducing yourself to everyone from The Rocks to Sydney’s business district as the lovable, if eccentric grandchild of the Sydney property developer Harry Triguboff.  No matter how many drinks it gets you, it is dishonest and it does make you a bad person.

If you do find yourself trolling Sydney, it is a sign you have been here too long. You’re becoming a Sydneysider.

Do not panic. Remember the final rule: know when to make an exit. Rise the next morning from the uncomfortable hostel bunk after spending the night listening to doof-doof club music pound up through the floor from the pub below, pack your bags, check out and head to the nearest train station. No one will know who you are and no one will care. That’s okay. As a wise lady once said, everything is transient. The main thing is that you will have won. You survived.

Heading to Brisbane next…

But there is a catch. This is Sydney and it is trying to screw you. You won’t see it coming and when you think you’ve won, it will get you with the $15 one-way train ticket to the airport you won’t quite be able to process until the guy behind the counter hands you back shrapnel. He looks at you kinda sideways, waiting for the next person in line, but you don’t move. You just stand there, feeling a little broken, thinking to yourself, “Fuck you, Sydney.”

“Fuck you.”

Love, Chester, your over-caffeinated T-Rex. xoxo.

Sydney is the fourth installment in a travel series about Australia.  If you want more, click to read about Canberra, Melbourne and Adelaide.