By Maisha Hasan, Local Journalism Initiative Reporter

There are very few moments in our lives where we end up in someone else’s shoes. And in the case of those less fortunate than you, there are even fewer moments where you want to put yourself in their shoes. United Way Halton and Hamilton (UWHH) present an opportunity for the previous notion to be considered, and in the name of a good cause. In their signature event “Sleepless For Our Community,” on February 21, hundreds of Halton residents will spend a night sleeping in their cars to gain a small taste of the struggles faced by those experiencing homelessness every night

This event offers an opportunity to connect with all members of the community — not only with fellow participants but also with those the cause seeks to support. With Sleepless For Our Community, UWHH aims to inspire lasting change through collective action.

Last year, more than 60 determined community members took part, spending a night in their own cars to raise awareness of the challenges faced by those experiencing homelessness and to support agencies working to help them. This year, participation has already grown, with 87 people registered so far—and UWHH hopes to see even more sign up before the Feb. 14 deadline. Fundraising efforts have also expanded: last year’s event raised over $265,000, and organizers are aiming for $300,000 this year. 

Kristen Jacob, the Vice President of Marketing and Communications for United Way Halton and Hamilton, shared her insight on the upcoming event. Answers have been edited lightly for flow and clarity.

Why is this event individually focused?
It’s an individual-based event and the reason for that is because for…folks in our community who are unhoused and who do not have secure living, it can be challenging — there is a sense of isolation felt where you are in the cold, in the evening, by yourself. So for the Sleepless For Our Community event, we do encourage people to do this in their driveways. Really, this is a gesture of wanting to come together for an act of solidarity for participants and help drive conversations around poverty and poverty-related issues. We do encourage individual participation just to get a sense of that isolation and a tiny glimpse into what folks in our community go through on a day-to-day basis, and many folks don’t have the opportunity to just go back indoors.

How does security work for this event? 
We always make security the number one priority. We do offer a checklist of safety tips for everyone: make sure they’re dressed warmly, have blankets, make sure their vehicles are parked in a safe location like a driveway or workplace parking lot, have your phone charged and handy, let someone have your location, pack food and drinks. And if you’re feeling unwell or cold, just go inside, we don’t want to put anyone’s lives at risk.

Where are all the funds from the event going?
All of the funds raised for the “Sleepless For Our Community” event go directly toward United Way-supported programs that are addressing poverty in Halton and Hamilton. This includes programs like transitional housing, food security initiatives, mental health support, job readiness programs, and things like financial literacy training. All of these programs try to create a pathway out of poverty for people, ensuring people have access to the tools and resources they need. So every dollar raised through this event goes towards these programs that are providing stability, dignity, and an opportunity for those people in our community who are the most vulnerable.


Executive Vice President of People, Culture, and Strategy Carrie Fletcher, of St. Joseph’s Healthcare in Hamilton, previously participated in the Sleepless For Our Community event and shared her experience of sleeping in her car for a night — alongside her teenage son.

Was there a process for setting your car up for the night? 
Yes. I did the community event with my 15-year-old son last year so that he could also get a small taste of what being homeless and out in the cold felt like. It in fact was one of the coldest nights of last winter for last year’s event. I took tips and tricks from individuals who had participated in the past including putting multiple layers of blankets beneath our bodies and overhead, wearing hats and mitts, and cracking our windows to get some fresh, yet very cold, air in so the condensation from our breath didn’t frost everything up.

How did the overall experience impact you and your understanding of the unhoused crisis? 
It really provides just a small glimpse into our housing crisis, but a glimpse we didn’t have previously. Even just being in the car at the set time to start the evening and being awake, it forces you to think through what those who live on the streets or in an encampment are going through. We still had the luxury of blankets and pillows for our house. The safety of being in our driveway, the knowledge that a warm house, indoor plumbing, and a cup of coffee awaited us in the morning. I think it was more profound for my 15-year-old son, who has led a more privileged life, to open his eyes to the youth who experience homelessness. It led to good questions and discussions with him. Those who are housed will never fully understand the crisis, but the more people that we expose to even a night in the cold, the more conversations that get sparked, and the more advocates we will have to find solutions.


Registration for this event closes on February 14. Participants each raise money for UWHH; adding a bit of competition is the “Scoreboard” tab on the registration page. Here you’ll find the participants ranked by the amount of money they’ve raised so far. Click on a participant’s name to find their personal fundraising page to support their cold night in the car and UWHH. 

Event sponsors include TD, Cogeco, Reliance, and First Ontario Credit Union, whose employees — along with UWHH team members — are among the event participants, highlighting a shared commitment to addressing poverty in the community.

If you are unable to participate but would still like to donate, visit the United Way Halton and Hamilton website.