Last night, I joined Covenant House’s Sleep Out: Executive Edition. For one night, I lay outside with only a sleeping bag and layers of clothing between me and the cold. The weather was mercifully chilly, but fortunately, no rain. Still, the ground was hard, the night was long, and the cold crept in despite my preparation.

Before we went outside, we gathered. Covenant House leaders shared about their work, and we participated in a group activity: if you were homeless tonight, what ten things would you pack into a bag? I found myself stuck. I didn’t know what to choose. Were my picks about what I wanted, or what I truly needed? That uncertainty was unsettling; and it reminded me that for homeless youth, those impossible choices are a daily reality.

We also heard from three young people at different stages of their lives. Their stories were raw and honest. What they needed most was not advice or quick fixes, but compassion, presence, listening, acceptance, and support, the kind of care that allows them to discover and live out who they are. They also carry trauma from broken relationships, abuse, neglect, and the harsh realities of street life. What they need is not judgment, but a community willing to stand with them, to listen, and to honor their dignity.

And let me be clear: we were not pretending to be homeless. There were over forty of us together. Staff blocked the alley, stayed overnight to watch over us, and made sure we could access the washroom, or even go inside for a hot drink or food if needed. I felt very safe and at peace there. That safety was a privilege, a reminder that my discomfort was temporary, while for youth on the streets, the risks, uncertainty, and trauma are constant. I am deeply grateful to the staff and leaders who guided us, cared for us, and shared their passion for this ministry.

In the past few years, I have reached out and served the homeless in different ways. Yet this night, though not truly a first-hand homeless experience, opened my eyes in a new way. It led me to think and act with deeper compassion and greater humility, reminding me that presence and solidarity matter more than assumptions or solutions.

This one night reminded me of four truths:

• Presence matters. Sleeping out did not solve homelessness, but it bore witness to it. It said: We see you; we care, we will not forget you.
• Preparation is a privilege. My nervousness and my bag choices showed how little I understand the daily calculations homeless youth must make—and how much courage it takes to live with so few certainties.
• Community is hope. Covenant House offers shelter, meals, counselling, and unconditional love. It is a reminder that compassion, acceptance, and support can break cycles of despair.
• We must fight stigma and trauma. Homeless youth carry stories, challenges, pain, and trauma. What they need is not judgment, but listening, presence, and solidarity.

I am grateful for those who supported me, donated, and prayed. Together, we raise awareness and resources for youth who deserve dignity, safety, and hope. My discomfort was temporary; their struggle is ongoing. May we continue to walk alongside them, not just for one night, but for the long journey toward justice and compassion.e dignity, safety, and hope. My discomfort was temporary; their struggle is ongoing. May we continue to walk alongside them—not just for one night, but for the long journey toward justice and compassion.