Chapter 8: Waking Up @ Portage & Main


this morning I woke up feeling cold, sore and disoriented. the small patch of grass I slept on was lumpy, but welcoming. It was a little surreal to have someone walking around and offering coffee to us as we woke up. I had quite the experience at this CEO Sleepout.

I arrived at Portage and Main at 6:30 last night. We all received a white t shirt and bright orange and green name tag so we could be identified. And then the speeches began. We heard from the programs who benefit from the CEO Sleepout, Kris Doubledee was there and we were even challenged to end homelessness in 10 years by several people. The speeches went on for about 2 hours, and I will admit it was hard to pay attention by the end of the formal program. The highlight for me was when Beverly of Red Road Lodge explained the impact that the arts can have in marginalized people’s lives to give them that spark of hope and confidence that could lead them to housing and reasonable employment. I was also very impressed with Candace Maxomywich who is a young politically involved woman who is very active and quite articulate.

At 9am, Robert Young had a brilliant idea of having people sign a document pledging their commitment to working on and implementing a 10 year plan to end homelessness in Winnipeg. It was called ENDING HOMELESSNESS IN WINNIPEG BY THE YEAR 2022. We got about 25 signatures.

Then, I had some visitors! Jenna Liiciious and Angie came by to say whats up! Jenna shared her beautiful singing with our group and brought the gift of her voice and her hand drum to all of us. Many people were inspired and moved.

At around midnight, myself, Jillian Taylor and Michael Anderson followed 2 other groups that had departed to check out the Salvation Army and Red Road Lodge. I was happy to once more connect with Al (and his dog Hunter) as he went into even more detail about what it feels like to have a supportive community like the Red Road Lodge staff to help keep him employed and feeling welcome. He emphasized how tight knit their community of 45 people becomes, and that turnover rates vary. Apparently Checque weekends and Saturday afternoons are the rowdiest times for those who work at the front desk at RRL. He also told me that in a few days, the arts resource centre would be closing due to lack of funding. That’s when My cell phone died.

After that I had a 2am date with Arry of Perfume Paradise and she gave me a great perspective. She explained to me how every CEO that was sleeping out tonight because of the compassion in their hearts to want to make an impact. She was happy and proud to be a part of an initiative that could raise over $100,000 to support programs that provide employment to homeless folks. As I was getting ready to depart from mine an Arry’s ‘date’, 2 interesting things happened

  1. she said to me “lions don’t have to roar. their presence is enough to silence a room’. This was shared because after speaking with many of these sleepout participants and hearing their own stories of why they were doing this, I was moved. And I felt defensive of them. And I wanted to respond in a negative way to people who were criticizing us. she reminded me of the teaching of humility and to remember that we are doing this event out of our compassion for others, and not out of malice for those who do not understand. she emphasized that their intention was not to simulate homelesness, but to raise money and awareness.
  2. and then, Gracie, my girlfriend showed up and spent the rest of the night huddled under our coats until the sun came up.

I remember walking away and having to pee.  My own personal pledge was to not take shelter, not take food and not use any of the bathroom facilities provided so I had to go down the backlane, find a corner and do my business there.

These small things like a place to go to the bathroom, or someone to sit and have a human conversation with you, are the things that many of us take for granted. This is homelessness awareness week, but I don’t want it to end here.

Let’s keep going, this is just the beginning, let’s do it together.

with love


there will be another chapter as I digest this experience and really percolate on what I saw and heard there

in the time being, check out the previous chapters in the CEO series


2 thoughts on “Chapter 8: Waking Up @ Portage & Main

  1. WOW Michael….you are the best!! You are so passionate about not just OUR people..but HUMAN KIND!!! You are a gently spirit who always reminds yourself about the 7 teachings and you are a great teacher with a very wise old soul! I love everything about you Michael – what an honour to say you are my friend….you keep on doing…making changes….bringing issues to light…. Keep strong my friend! In friendship – Haven

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