Self Reflection Questions
Understanding, Reflecting, and Engaging: A Guide to Exploring Homelessness, Bias, and Privilege
Why These Questions Matter
This section is an invitation to pause, reflect, and get uncomfortable. Homelessness and addiction isn’t just about “bad choices” or “bad luck”, it’s the result of complex systems shaped by colonialism*, capitalism*, racism*, and patriarchy*. Too often, unhoused people are spoken about instead of listened to, and reduced to stereotypes instead of recognized as full human beings.
These questions are here to help you examine your own assumptions, blind spots, and privilege. Some will feel simple, others may sting, and a few might challenge you to rethink the stories you’ve always believed about homelessness. That discomfort is not a sign to turn away, it’s a sign you’re growing.
We encourage you to sit with these questions slowly. Journal about them, talk about them with a friend, or just notice what feelings come up. This isn’t about guilt, it’s about awareness, empathy, and beginning to see how we are all connected in systems that either uphold or challenge inequality. This is how we begin to create change.
*Key Terms and Concepts at the bottom of the page
How to Engage With These Questions
These questions aren’t meant to be rushed through, they’re an invitation to pause, reflect, and grow. Here are some ways to engage:
Journal privately – Write down your answers, reactions, or even just the emotions that come up. Notice where you feel defensive or uncomfortable—those moments often hold the most insight.
Discuss with a friend – Pick one or two questions to talk about with someone you trust. Sometimes saying things out loud helps uncover perspectives you didn’t know you had.
Group conversation – Use these questions in a book club, classroom, yoga circle, or community gathering. Each person can choose one question that resonated with them and share their thoughts.
Pause in daily life – Carry one question with you during your day. Notice how your thoughts or behaviors shift when you see or interact with unhoused people.
Creative reflection – Draw, paint, collage, or use another creative outlet to express what comes up for you. There is no “right” answer—just exploration.
Social accountability – Share a question (and your reflections if you feel safe) on social media. Invite others to think about it too—sometimes the ripple effect is bigger than we realize.
Reflection Questions
1. When you see someone who is unhoused, what’s the very first thought that crosses your mind? Where do you think that comes from?
If your thought is something like “why don’t they just get a job” or “why don’t they go to rehab,” pause and consider: What barriers actually exist to getting a job, going to treatment, or “saving money”? How does a lack of housing, stigma*, untreated trauma*, or systemic racism* make those steps nearly impossible?
2. Do you tend to feel fear, pity, annoyance, or compassion when you pass an unhoused person? Why?
Have you ever asked yourself where those feelings come from? Are they rooted in personal experiences, stereotypes, or media portrayals?
3. Have you ever asked someone who is unhoused their name or how they are doing? If not, what has stopped you?
If it’s fear, what exactly are you afraid of? If your fear is of being attacked, where does that assumption come from? What might shift if you simply smiled or said hello? Do you avert your eyes when you see someone unhoused? If so, what feelings are you avoiding: embarrassment, guilt*, shame*, sadness? What would happen if you leaned into that discomfort instead of away from it?
6. Do you ever assume people on the street are there because of “bad choices”? How does that belief uphold systems that keep people unhoused?
Think about a time when you made a series of bad choices because you were hurting, stressed, or not in a good headspace. What safety nets kept you alive? Friends? Family? Being white? A savings account? A job that gave you second chances? How might your life have looked without those supports?
7. In what ways do you benefit from a society that criminalizes and marginalizes unhoused people (e.g., policing, bylaws, gentrification*)?
Consider: when parks are “cleaned up,” when benches are designed so people can’t sleep on them, or when shelters are over policed, whose comfort is being prioritized? How does your own sense of safety, convenience, or property value increase because someone else is displaced?
8. When you donate money, food, or time, what does that give you emotionally? What power dynamics exist in that exchange?
How might those power dynamics be harmful? Do we sometimes assume we know what’s best for unhoused people instead of asking and trusting them? How does it feel to give without control, without judgment, and without conditions?
9. How have colonial* policies (e.g., land theft, residential schools, displacement of Indigenous peoples) directly created pathways to homelessness in Canada?
If you’re not familiar, pause and research: How does the destruction of land-based ways of life, the intergenerational trauma* of residential schools, and the ongoing removal of Indigenous people from their territories show up today in housing insecurity and overrepresentation of Indigenous people on the streets?
10. What role does anti-Black racism* play in how people are treated by housing systems, police, and shelters?
Why is it important to examine anti-Black racism? Because when we see how anti-Blackness operates, we start to see how all systems of oppression are connected. If you are white, imagine how you might be treated differently in the exact same circumstances if you were Black, Indigenous, or a person of color.
12. Whose voices do you trust most when learning about unhoused individuals: professionals, media, politicians, or people with lived experience? Why?
What happens when we center people with lived experience as the experts of their own lives? How might that shift the way services, supports, and solutions are designed?
13. What would happen if you lost your job, had a medical emergency, or left an unsafe relationship tomorrow? How many paycheques away are you from being unhoused yourself?
And beyond money, what about your relationships? If you had family or friends to fall back on, you might be able to figure things out. What happens if someone has no support system, no savings, no cushion?
15. When you see police moving unhoused folks out of parks or public spaces, whose comfort is being prioritized?
What values are being centered: public image, property values, middle-class comfort, or human rights, dignity, and safety?
16. What privileges allow you to look away from homelessness when it’s inconvenient or uncomfortable?
What stops you from making eye contact, offering a hello, or even acknowledging someone’s existence? How does privilege allow you to disengage while others don’t have that option?
20. What would a truly supportive, human-centered community* look like to you?
What would it mean to build a community that centers care, dignity, and connection over profit, property values, or appearances? What role could you play in creating that?
Key Terms & Concepts
Anti-Blackness
A specific form of racism directed at Black people that includes systemic discrimination, stereotypes, and violence. In housing and policing, anti-Blackness shows up in overrepresentation of Black folks among unhoused populations and disproportionate criminalization.
Blind Spots
Areas of bias or privilege we can’t easily see in ourselves. They shape how we perceive others and can lead to harmful assumptions if left unexamined. Reflecting on blind spots helps us grow in awareness and empathy.
Capitalism
An economic system that prioritizes profit and productivity. Under capitalism, people who cannot “contribute” in traditional ways—because of disability, illness, trauma, or systemic barriers—are often devalued and excluded.
Colonialism
The process by which powerful nations took land, resources, and autonomy from Indigenous peoples. In Canada, colonialism continues today through policies and systems that displace Indigenous communities, limit access to housing, and disrupt cultural continuity.
Gentrification
The process of wealthier people moving into historically working-class or marginalized neighborhoods. While it often brings new development, it also raises rents, displaces long-term residents, and erodes cultural and community roots.
Guilt
A feeling that arises when we believe we’ve done something wrong. Unlike shame, which attacks our sense of self, guilt can motivate repair and accountability if approached with compassion.
Human-Centered Community
A community that prioritizes care, dignity, connection, and support for all people—especially those who are most marginalized—over profit, appearances, or convenience.
Intergenerational Trauma
The transmission of trauma from one generation to the next. In communities affected by colonization, residential schools, slavery, or war, trauma shows up not only in individuals but also in family dynamics, cultural loss, and systemic oppression.
Patriarchy
A system where men—especially cisgender, heterosexual men—hold primary power in social, political, and economic life. Patriarchy intersects with colonialism and capitalism, shaping who has access to housing, safety, and belonging.
Power
The ability to influence or control resources, decisions, and systems. Power can be visible (like political authority) or invisible (like social privilege). Reflecting on power means asking: who benefits, who is harmed, and who is left out?
Privilege
The unearned advantages and opportunities you have because of aspects of your identity (such as race, gender, class, or ability). Privilege doesn’t mean your life is easy—it means it isn’t made harder by certain systemic barriers.
Shame
A painful emotion that tells us we are bad or unworthy. Shame thrives in secrecy and silence, often keeping people from seeking help or connection. Healing shame often requires compassion, vulnerability, and safe community.
Stigma
Negative attitudes or stereotypes that mark someone as less worthy or “other.” Stigma often surrounds issues like homelessness, addiction, or mental illness, creating barriers to care and belonging.
Trauma
A lasting emotional response to deeply distressing or harmful experiences. Trauma affects the body, mind, and relationships, and can be both individual (like an accident) or collective (like colonization or systemic violence).