The Illawarra's business and community leaders are being urged to forgo one night of comfort to help make a difference to the lives of those less fortunate.
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The Wollongong Vinnies CEO Sleepout was launched on Thursday.
The St Vincent de Paul Society's Wollongong Central Council is calling on Illawarra business and community leaders to commit to spending a winter night outdoors on Thursday, June 20.
Read more: The hidden faces of the Illawarra's homeless
About a dozen CEOs have registered so far; more than 30 took part in 2018.
The event aims to raise funds in support of Vinnies' frontline services.
This year's sleepout will be held at the University of Wollongong's Innovation Campus for the first time in the event's eight-year history.
Wollongong-based Anna Tydd, executive officer of the Implementation Advisory Group will be participating in her first CEO Sleepout.
"Vinnies do such amazing work, so if I can contribute in this way then that's pleasing," she said.
"Considering the comfort that most CEOs generally experience in their lives, one night of sleeping outside is very minor, and it's just such an important cause."
Meanwhile, Danny Munk from the Aster Group (Wests Illawarra) is participating in his fifth CEO Sleepout.
He has raised more than $100,000 for the cause to date, making him the sixth highest fundraiser in the state since the inception of the national event in 2006.
"Each year is a learning experience both in regards to what's happening outside in the community and how the homeless situation is impacting us, but also understanding that it's not something that's shrinking - it's growing," he said.
"People in our community that can't be guaranteed a roof over their head or a warm bed of a night, means there's still things that we need as a community to fix.
"It impacts everyone, and everyone needs to get on board."
As part of their night in the cold, participants will hear first-hand from people with lived experience of homelessness and housing stress, and learn more about the valuable grassroots assistance Vinnies provides.
Vinnies' Wollongong Central Council executive officer Peter Quarmby said they weren't aiming to trivialise homelessness by hosting the sleepout.
"I suppose the biggest take-home message for the people participating is we've got the choice.
"We can go home, and there's a nice doona waiting for us at the end of that sleepout.
"The reality is for so many people, they don't have that choice. So they're either sleeping rough, couch surfing or just have no security of housing.
"We hope to foster awareness of the reality of the issue - young people, women and families resorting to couch surfing, overcrowded accommodation, living out of cars or sleeping rough - and focus on educating and supporting business leaders so they can best assist those experiencing disadvantage and homelessness."
Organisers have set a fundraising goal of $200,000, following last year's $170,000 record total for the Wollongong event.
The $200,000 fundraising goal for the 2019 event will help support the continuation of existing homelessness and mental health services across the Illawarra, Shoalhaven, Macarthur and Southern Highlands.
The public can sponsor a participant or donate here.
The 2016 Census figures showed that in NSW, the number of people experiencing homelessness increased by 37 per cent between 2011 and 2016 to more than 37,700.
Homelessness in women aged over 55 is on the rise, and NSW has seen a 36 per cent increase in the number of 12-24 year-olds without stable, secure and appropriate housing, with family violence being a key driver of this statistic.