CEO Sleepout - A day in the life

Australia, Jun 26, 2024

Published by Logicalis Australia
Topic: CEO Sleepout - A day in the life
Expert: Anthony Woodward, CEO, Logicalis Australia 


Hi all,

As you may know, I’ve just completed my 13th Vinnies CEO sleepout, to raise awareness and funds for homelessness.



What is the Vinnies CEO Sleepout?

The Vinnies CEO Sleepout is a one-night event held on one of the longest and coldest nights of the year. Hundreds of CEOs, business owners as well as community and government leaders sleep outdoors to support the many Australians who are experiencing homelessness and people at risk of homelessness. Over the past nearly 20 years Vinnies has raised over $90m in the fight against homelessness.

Next year is the Vinnies CEO Sleepout 20th anniversary. Will I be back? I will keep coming until homelessness is in the past.

What happens at the sleepout?

I have been getting a lot of questions about what happens at the sleepout, so I thought I’d answer this in the form of a timeline. 

5pm Thursday: Arrive home from work and school pickup, and pack my sleeping bag, a pillow, water bottle, lollies (for the 3am grind), headphones, eye mask and tracksuit. Change into thermal woollen top and warm jacket plus sleepout beanie from a prior year. Uber to the event.

6pm: Arrive at White Bay Cruise Terminal, Glebe and check-in.

6.30pm: Take part in the ‘lived experience’ pilot, where we role-play someone facing the threat of homelessness. I play the role of Amanda, who is escaping domestic violence with her young children, and had to leave her home urgently without any money, ID, or phone.  

First stop, Centrelink: no ID, no payment.  

Service NSW: no money, no replacement ID.  

Back to Centrelink : definitely no money with no ID. Here’s a referral to a GP as you seem to be getting anxious.  

GP: I can write a script for your anxiety, but it’ll cost you $$ to fill. Maybe try Vinnies – they may be able to help.

Vinnies could fill the script, for free, sort out some emergency accommodation for tonight, and some cash to feed myself and the kids. This is how Vinnies close the gap between those in danger and government services, which can’t help if you’re on the run.

6.45pm: Hear from a Vinnies customer: She and her four kids were shut out of their Mosman home by a controlling husband who thought she would leave and drained all her bank accounts while she was flying back to Australia. She spent 8 years, including through Covid, in various forms of temporary accommodation, home schooling 4 kids, and self-representing through the family court system against her ex’s expensive legal team who saw that she ended up with nothing - not even her own pre-marital assets, or maintenance payments. Vinnies were able to help with renting suitable accommodation, financial support for the basics – groceries, furnishings, etc – and now with a legal strategy to try and get some of her own assets back through the court system.

7:30pm: Formalities begin with Deb Knight (nine media) MCing as we hear from others who have had the need to lean on Vinnies, including those escaping family violence, those who lost their job and then their housing, those with severe alcoholism. Matt, for example, went from a high flying stockbroker to meth addict on a park bench with nothing, having lost both parents, his job, and his home, before Vinnies saved him.

9.30pm: Dinner of soup, bread roll and cookie from Our Big Kitchen, charity food providers who work the streets every night.  


10:00pm: Closing of formalities with the winner for the highest fundraising team announced. You can find out more on the leaderboard here: Fundraise for Australians experiencing homelessness - Vinnies CEO Sleepout 

10:30pm: Set up the sleeping bag and cardboard lean-to  


11:00pm: Try and get warm, set up my trick hip cushion in the form of my warm jacket folded up inside the sleeping bag. Drift in and out of sleep.


1:00am: 10 degrees. Hip A is very sore. Rest on the back for 5 minutes. That’s sore. Turn to hip B. Doze for 20 minutes. Leg Cramps! Must be the cold. Got to stretch out. Rinse, repeat until 3am.

3.00am: 9 degrees. Do I really need the loo? Hold out for 20 minutes. Nope, I’ll have to exit the sleeping bag and sort that out.

3.30am: 9 degrees. Back into the sleeping bag and into the right/left hip dance. Drift in and out of sleep.

5:00am: 8 degrees. I actually got some sleep, through exhaustion.  

5.30am: Do I smell bacon? And coffee? Time to get up and get in line for some.

5.45am: Packed up, brekky roll and coffee in hand, reflecting on the night with some of the other snorers. 


6:00am: Uber home to start the day.

This was one night. Tough, but compare that with years of homelessness and wondering about your safety every night.

Thank you all for your supporting donations and good cheer, including attendance at the Logicalis Sydney breakfast and Melbourne afternoon tea over the last few weeks.

It’s not too late to donate:

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