Covenant House: Sleep Out Next Generation

I looked outside with apprehension — pouring rain, dreary skies and a temperature of 2 degrees. I was participating in the Covenant House Next Generation Sleep Out tonight — sleeping outside with only a sleeping bag and piece of cardboard to raise money and awareness for the youth shelter. Not exactly perfect weather… but I was pumped to test myself in tougher conditions.

Gearing up for my first street sleep out

As Canada’s largest homeless youth agency, Covenant House Toronto changes lives by providing a wide range of services and support under one roof (crisis shelter, job training and counselling, onsite high school, health clinic, transitional housing, foodbank, culinary training school and mental health services). I visited the center a week before the Sleep Out and was blown away by the scope of the services. The operation is massive with a budget of approximately $25mm, of which the majority is raised through a private donor network and events like the Sleep Out. Covenant House supports up to 250 youth per day and the front-line staff are among the country’s leading experts, who help young people overcome problems like abuse, neglect, addictions, mental illness, prostitution and gangs. Antonia, Meghan and the other staff I met were so passionate about this cause it seriously made me think, “how I can have a more meaningful life?”

Covenant House makes a promise (“covenant”) to support youth every step of the way to independence. Youth workers develop a plan tailored to the individual needs and goals of each youth. Plans include all the objectives they set for their stay, such as looking for a job, going to school or learning life skills. Every youth at Covenant House is working towards independence with the careful ongoing support and encouragement of a dedicated youth worker.

My friend Andreas told me about the Sleep Out challenge (he’s a two year sleeper that raised more than $25K this year… $10K of which he donated himself!!!). At first, I was more interested in conquering the actual challenge: sleeping on the street in the “winter” and raising $2K through my network were both uncomfortable (I find it hard to ask for support)— to be honest, these are kind’ve selfish reasons, but they got me to take the first step and sign-up.

Three of my classmates — Andreas Antoniou, Shamez Virani and Event Chair Dave Armstrong

My initial goal for the Sleep Out was to raise $2K. I started with a personal email to a handful of high impact individuals with similar core values. The initial response was fantastic (THANK YOU!) and drove me to learn more about youth homelessness in Toronto — what I learned was pretty terrifying (but keep in mind, this is a positive story about inspiration and resilience):

  • It is estimated there are 1,000–2,000 homeless youth on a given night in Toronto
  • 50% of homeless youth come from middle- and upper-income families
  • 30% of homeless youth have been involved in some form of the sex trade
  • In Toronto, half of street youth surveyed said they had stolen food or eaten food that had been thrown out
  • 23% of women and 11% of men said they’d resort to trading sex for food

Because the Covenant House facilities were so impressive, my initial fundraising response was very strong, and the stories I heard during my initial trip to Covenant House were so shocking— I decided to stretch my fundraising goal to $5K. The larger goal required a lot more effort and certainly put me out of my comfort zone… I had to bother friends with multiple phone calls, drop-ins and even offer free consulting services. Sorry for the hassle everybody, but the result was totally worth it! As a group, we raised $370K and beat the target goal by 50% — far beyond the organizers boldest hopes. In addition to the $5K, I also enrolled my girlfriend Emily, my cousin Levi, his girlfriend Mercedes and one of my best buddies Brandon Farmer to join: Between the five of us we were able to raise $15K on pretty short notice!!

The whole group posing for a picture pre-sleep out

Again, being honest with myself, I think I was still primarily raising money because I’m competitive, but during the Sleep Out event, I went through a huge shift in mentality. The event started with a dinner in the gymnasium prepared by the Youth in the “Cooking For Life” training program. The dinner was followed by speeches from a panel of 4 former Covenant House Youth that had used the services successfully. The speeches taught me a lesson I really needed in both gratitude and human resilience:

  • I heard stories of youth being kicked out of their homes that really resonated, one at the age of 17 for admitting he was gay and another at the age of 19 for not performing to expectations in university.
  • Another girl left an upper middle class home due to abusive parents and came to Toronto by bus at 16 — alone. She spent time sleeping in abandoned apartment hallways and on park benches before finding Covenant House.
  • Jobs were tough to get because youth had no stable address and weren’t able to get ID. They also had no training or preparation in budgeting, credit, creating a resume, interviewing, etc. It was impossible to have any belongings because they would be stolen while sleeping.
  • There were terrifying stories of runaway youth being first coerced and then forced into prostitution / drugs. Some were even kidnapped and trapped in hotel rooms. The reality was worse than I’d seen in any movie.
  • For many this was the first time living alone (Covenant House supports youth between 16–24) and they had minimal experience with the household tasks of an adult (laundry, cooking, groceries, bill management). Most had no education regarding nutrition or healthy lifestyle. Imagine being homeless with none of the tools required to improve your situation and massive fear dealing with the struggle alone. I remember being terrified going to university at 18 and spending the first few days alone without friends/family — crying because I was on my own for the first time — I can’t even imagine what that would be like with no support or shelter.

I’m embarrassed to say that prior to the event I had a misconception about homeless youth — I’m not sure why, but I had the feeling most homeless youth were homeless due to their own choices (ie. dropped out of school, got addicted to drugs, etc.). Watching the speeches, I realized that I could’ve easily been in the same situation — the only tangible difference between us was environment. This filled me with a lot of gratitude. I had been stressed that day about some menial deadlines I was facing at work, and listening to these inspirational stories immediately put me in the present moment — “wow, I am lucky, the support I have had and life I have lived is incredible”. This was a very powerful reminder that I take life for granted every day. Being in the present moment with gratitude is what makes life feel valuable and real. It wasn’t just gratitude though, I was also inspired. The stories of the resilience of these youth and the kindness people have shown at Covenant House made me proud to be a human being.

  • I heard about individuals getting guidance around all of the issues outlined above. Youth excitedly explained their first job, first managerial position, first ever home in which they lived alone — fully financed on their own. Many of these were options available through Covenant House guidance.
  • Youth talked about career / interview counselling and using the Covenant House as a stable address for employment. One youth talked about being accepted into University (she had initially applied as a joke and couldn’t believe she was accepted). One former youth also had gotten a job a Fairfax, a premier financial firm.

For the first time, I started to clue into the magnitude of the Covenant House Mission. Covenant House is a foundation building youth’s self-esteem and bringing out the best in people who have been challenged beyond what most can believe. The mission is to help those who can least protect themselves access their strengths so that they can truly build a new life.

Being honored with a Scarf for raising more than $5K was has me feeling exhilarated

I spend so much of my time concerned with “I”, how can “I” improve at work to get that promotion, “I” need more time to exercise this week, “I” need to make more to support my family, “I” want to buy that new house/car/clothes to feel good, “I” want to be happier, “I” need a vacation, “I” want to spend more time with friends etc. This is the way the mind works, but what really makes us happy is focusing on the “we”. Hearing about the struggles of others, their resilience and the help they received — this is what builds our sense of “we”. The “we” is what really made me feel connected to others. I thought, life is hard and “we” really are in it together. Thinking of others is truly what it means to be human and I was so fortunate to feel that at Covenant House — finally, I realized, this was the real reason I was donating my time and effort. So again, thank you to all my donors for taking part, I hope you feel the same as you have earned that good karma!

The rest of the evening was empowering — I haven’t felt that sense of pride in some time. Extreme pride in my friend group. Classmates Dave Armstrong, Shamez Virani and Andreas Antoniou who all sat on the event committee (Dave was the Event Chair and over the last three years has grown the event at a rapid pace — he also gave a fantastic speech). Extreme pride in the Covenant House Youth — watching those in the cooking program beam as the room exploded in applause for the food and presentation! Extreme Pride in humanity — watching volunteers around the room bidding up the price of auction items, smiling and supporting an amazing cause. The evening was empowering, everybody there was empowered for those few hours and looking around, I realized that I fiercely want to empower people. That’s the way to live life and is an amazing personal mission!

Just before the Sleep Out, we sat in on an intimate talk with a former “Gang Member” that now spends his time counselling youth on the pitfalls of that lifestyle. This was one of the most captivating / terrifying stories I had heard from somebody live. At the age of 13, his father left and his mother forced him to start dealing crack cocaine to support his family. He spent years involved in drug dealing and the prostitution trade and served multiple sentences in prison. After his last stint in prison he decided to become a symbol for youth, and quit illegal activities in order to spend more time at home with his daughter. However, while he was in jail, his daughter resorted to street life to survive. Listening to his daughter’s story and learning about the pimp’s name tattooed on her back was crushing — knowing what that meant and knowing first hand what she had to endure was something he said he would have to live with forever.

That’s my beautiful girlfriend Emily

After the dinner and speeches it was time for The Sleep Out, which was much harder than I expected. It was raining fairly hard and was quite cold for an evening in April (it would snow during the morning hours). My feet got wet in the rain on the walk over and were cold the rest of the night. The cardboard was extremely uncomfortable on flat concrete and it was both cold and raining. I have been basically living in the jungle for the past few months, so was surprised at how hard it is to sleep on the street! Emily and I were both pretty sore and tired at work the next day. So as a donor — you definitely “stuck” it to us. The charity funds were certainly! When we all woke up around 5am, it continued to snow. Keep in mind, this was for a single evening in April (I can’t imagine living homeless full-time during the winter).

This was the standard cardboard setup

Overall, what a great practice for building gratitude! Despite the uncomfortable physical conditions, the event was fun and I woke up energized. Luckily, I was able to share a sleeping bag with my lovely girlfriend and was surrounded by friends and positivity = and I was again reminded, a connection to others, compassion and support is what we really need to get through hardship. This is the most important thing a human being can ask for and the Covenant House lives this mission by providing connection, support and compassion to those who need it most. Now the questions is, how can I get more involved for next year!

Thanks for reading! Please recommend the article to help build awareness (button at the bottom) and feel free to share the link with friends or via social media. Also, if you are interested in participating next year or becoming a donor — feel free to email me at for more info.

One of my Best Buddies Brandon — He’s aiming to get his entire Tim Horton’s Empire behind him next year