His crate is his stage, and he performs to crowds focused only on the departing train at the end of the tunnel. Commuters walk to a different beat – the pulse in their white earbuds. Regardless, Kit Sherring sings and strums for those who are listening.

It’s the same song as yesterday, and the day before, but he plays with no less gusto than a year ago. Yet this is no surprise, because he’s got a strong incentive.

If Kit doesn’t make enough, he and his brother – who’s rapping at Circular Quay – will spend the night on Sydney’s streets.

Roughly 272 people are dispersed across the streets of central Sydney on any given night, while a few hundred other homeless people will sleep in crisis and temporary accommodation beds.

However, there are many other homeless people: those who are neither on the streets, nor have been able to secure a bed in crisis accommodation, but spend the night elsewhere.

One homeless guy the other day told me he woke up and his shoes were gone. Off his feet!

Arlie, a young man who’s under 25 might be on a friend’s couch, or in a 24/7 internet café. Kit and his brother might be in backpackers’ accommodation. Others still, might be in a 24-hour gym or some other overnight business that provides an unintended sanctuary.

The most important thing is getting inside after dark. A night on the streets is the scariest part of being homeless. If not in a bed, Kit, aged 27, and his older brother must find somewhere where it’s dry, private, and where they have less risk of being attacked. When it’s raining, this might mean finding an abandoned house.


The pedestrian tunnel under Central Station where Kit busks to raise money for accommodation. Photo: Clara Janssen

Kit explains the risks that face those who can’t get inside by dark,

“You get thieves in the night,” he says. “One homeless guy the other day told me he woke up and his shoes were gone. Off his feet! Like yeah. How do you sleep through that, for one. But yeah, that stuff happens all the time.”

Rosalind, a small woman, leans against a pillar at Central Station, holding out a disposable cup containing a few coins. She is about four metres and $8 away from the pork roll with salt and gravy that she hungers for. Yet, she straightens her posture and a smile spreads across her face as she tells me that despite spending her share of nights in homeless shelters, she’s now off the streets. She has her own home, and only has to come to the station for food.

While shelter is the greatest need for a homeless person, it is also the hardest commodity to acquire. Food, which is also a necessity, is easier to come by. Free food vans are scattered across the city, giving out food in abundance every night. There are often also passers-by who are willing to buy food for homeless people. Shelter however, is what homeless people are always chasing.

It just felt like I was being kicked aside.

In Sydney’s city, services for homeless people are plentiful and bystanders remind homeless people of this often. Kit says that he’s told “probably 70 times a day… they say it like I’m an idiot”.

Yet all of these services come to an end. Despite the vast array of services, once you’ve used them, you can’t use them again. For example Headspace, which is a mental health service, ends when recipients turn 25. Despite the great strides Kit made with Headspace, the limit on it left him frustrated.

“I just felt like, as soon as you’re over 25 your mental health isn’t important anymore,” he says. “It just felt like I was being kicked aside. That I still had so much work to do, and I had to do it on my own. Or I had to figure out a way to pay for it, you know, and I couldn’t pay for it.”

Many shelters for homeless people also end up being short-term solutions to a long-term need. Depending on the homeless shelter, homeless people may be able to stay for five days, 28 days, or three months before facing the service’s inevitable end.

Shelters such as Matthew Talbot Hostel offer support to homeless men through case workers who continue to help homeless people once their stay has ended, while organisations like Mission Australia Blacktown also provide case management support, involving an assessment with the client, and the assigning of a case worker to each homeless person, to help them find housing.

During the process of organising temporary accomodation for homeless people, many organisations such as Link2Home will also begin the application process for a homeless person to receive permanent housing, by placing them on the housing waitlist. Depending on availability, the wait for permanent housing may take years.

The success and speed of this support depends on many factors including the “client’s willingness, income, and engagement,” says Michelle from Mission Australia Blacktown.

Yet, many homeless people do not pursue this support because they are more concerned with finding shelter for the day at hand, than organising shelter to meet their long term need. As a result, many homeless people end up jumping between organisations as they use up their temporary accomodation from each one.

Most people think he’s in his 40s… He’s 28.

At the mention of homeless shelters, many homeless people I speak to shrivel up their faces or physically retract. The overwhelming implication is homeless shelters are not pleasant places. When asked about them, Kit describes them as “dingy” and “cold”, but also acknowledges expectations can’t be too high for a free service.

Even so, there’s another reason why Kit tries to avoid homeless shelters.

It was drugs that drove him to homelessness a year and-a-half ago, and Kit’s seen first-hand the harm and devastation that drugs can cause in the life of his brother, who was a heroin addict.

“Most people think he’s in his 40s… he’s 28,” Kit says.

As he sips his Pepsi, he tells me that his avoidance of homeless shelters is an extension of his efforts to escape the way of life he was once involved in.

“I’ve tried to avoid them pretty religiously,” he says. “Not because they’re dangerous or anything, just because that was the life that I used to be involved in and that, that’s what I want to stay away from. You know?”

Since then, Kit has deleted the contacts of his drug addict friends, his drug dealer contacts and now doesn’t have a phone at all, but a battered tablet with a broken screen.

These are the conscious decisions he has made to escape his old habits. “I don’t want to be sucked back into it. Into that world. And it’s so easy to fall back into it,” he adds.

Despite the monetary, physical and emotional cost of this drug, a high proportion of the homeless community in Sydney is still dependent on heroin. In a tumultuous reality, the only peace many can find is that which comes from drugs. But falling back in, as Kit describes it, looks like “disappearing off the face of the earth, not caring anymore… it’s not pretty”.

Railway Square YHA Backpacker Accomodation above Central Station

Railway Square YHA Backpacker Accomodation above Central Station’s pedestrian tunnel. Photo: Clara Janssen

For Kit, the temptation to cave-in is strong on a high earning day busking, but instead, he and his brother put their earnings towards beds in backpacker accomodation.

Kit points across the station as he shows me the “less nice” and the “nicer” one. Of course there are others too, but Kit’s learnt the hard way that the $20 price tag isn’t such a bargain when bed bugs are involved. The better ones are $40-$50 – a lot more busking!

He borrows my phone to text his brother.

“Hey bro…just going back to the tunnel,” he types.

Soon Kit might not only have a secure bed, but a couch and a fridge as well. The Neami Way2Home scheme promises department housing with a 10-year lease, and in the three-month wait, clients are given a hotel room. That’s why it’s imperative that Kit is back in the tunnel to retrieve his birth certificate from his brother.

We might not be hearing the strum and song of Kit Sherring in Central Station’s tunnel for much longer, but that’s only because “hopefully everything will be sorted soon… so yay!”

Main photo: Homeless busker Kit Sherring. Photo: Clara Janssen