Two dozen politicians, community leaders and members of the media have just finished a day and night experiencing homelessness.

The Hard Night Out event, organized by the Manitoba Harm Reduction Network, was the second annual event pairing homeless people with others in the community. Organizer Daryn Bond says the event expanded this year to incorporate another struggle faced by people who live on the streets.

"We extended the event this year into the business day, so people could actually see a little bit about some of the barriers to accessing services," Bond told CBC News.

"Some people went to employment services, some people tried to get ID. Some people just went around to different places, so people would be able to see how they were treated."

Participants in the event also took part in a panel discussion last night at the Freight House Community Centre, where homeless people told their stories. The event wrapped up Wednesday morning with a breakfast at the Siloam Mission.

'Very entrepreneurial'

Winnipeg Chamber of Commerce boss Dave Angus participated in the event. He was paired with Grace and Leon, a couple who lives on the street, and was surprised to find they shared some traits with the people he works with every day.

"I've got to tell you, as somebody who deals with entrepreneurs every day, these people are extremely entrepreneurial," he said.

"We spent the day really looking for cans, because they crush them, they put them in a bag, and they take them to a place that gives them money for tins. They choose not to steal or engage in any criminal activity to get money. They, in a very entrepreneurial way, go out for ways to look for money and get by every single day."

Angus hopes the event helps raise awareness of the need to help the city's truly poor.

But he doesn't think it's as simple as simply giving such people jobs. Angus says many of the people he met simply don't have the life skills needed to function in mainstream society.

For that reason, Angus says the support systems to help people from the street need to be bolstered.