CEO Sleep Out Tips for First-Timers

Our community is taking strides to raise awareness and much needed funds for homeless programs in Winnipeg. For the fourth straight year, CEOs and community influencers will be sleeping out on the corner of Portage & Main to help end homelessness in the city’s downtown.

Some have been participating in the event since its launch; however, this year, we are welcoming 50 new participants. This will be my second year, but I’m certainly no veteran.

Since I was at last year’s event, and someone gave me some tips and tricks for sleeping outside; I thought I would share some insight of my own.

Here goes:

1. Wear layers -
2. Make sure you have comfortable footwear
3. DO NOT; I repeat, DO NOT bring a tent.
4. Wear pants with pockets and leave valuables at home
5. Get there early to snag a good spot (but not before me, just saying)
6. Don’t forget your sleeping bag 
7. Coffee has a dual purpose, whether you drink it or not, you will have to have some coffee – not only to stay warm but to stay awake through the tours.
8. Be prepared to socialize, mingle, and meet new people – I met some people at last year’s event that have turned into great friends, colleagues, and acquaintances. You may not meet everyone, but be prepared to socialize with most.
9. Charge your phone before going, you’ll be asked to use social media throughout the evening
10. It is very likely, and highly probable that you won’t sleep… AT ALL. You’ll try, and you may succeed, but if you do, you certainly won’t know for how long. Just saying.

Remember, the CEO Sleep Out is in no way meant to mimic or ridicule the homeless – we participate in the event to raise funds following up-to, and awareness throughout our experience.

Last an certainly not least, it will change your perspective on homelessness – however, this is not something that you can prepare yourself for, because everyone takes something away with them in their own perspective.