Should I Give Money To Homeless People? (4 Questions Behind The Question)

In my year of working for Seattle’s Union Gospel Mission, I’ve been asked this question more than anything else.

“Should I give money to homeless people?’

In response, I have several questions for us to think about:

1. What Will I Trust?
When I walk by a homeless person standing at a street corner on my way to lunch, I will trust something. I may trust the words of the cardboard sign they are holding. I might trust they will use the money I give them for what the sign says it will be used.
I may trust a predetermined decision I made awhile ago. Perhaps it’s even something someone at my church told me that led me to the conclusion to never give money to homeless people. I trust this is the wisest course of action and I may even be right.
I will trust something in that moment. There’s no getting around it. Lately, I’m daring to choose Jesus as the one I trust. I’m trying to ask him what he wants me to do as I pass by a homeless person.
To be honest, it freaks me out and I think that’s why I’d rather trust anything else but Jesus. I’m scared to death of what he might say. It’s because I know his reputation and what he’s told people to do in the past and I’d rather just not go there.
Homeless in New YorkAlso, he tends to be unpredictable. For instance, he never healed a person the same way twice in the Bible. So, there’s been times he’s just asked me to pray for the person. Other times, he’s asked me to sit down and have a conversation with the person. A couple times, He’s even asked me to give the person some money. There was this quiet peace that came with that decision almost as if God knew what the person would do with the money and it was going to be something healthy. I’m wondering if it was maybe even an answer to prayer.
What are you trusting?

2. Am I After Comparison Or Compassion?
Sometimes I wonder if the predetermined decision, “Never giving money to homeless people” is just as unhealthy as the statement, “I always give money to homeless people.” Both allow me to pat myself on the back for a job not well done. With the first statement, I pat myself on the back for being wise. The second statement, I pat myself on the back for being generous. If I’m not careful, both of the decisions are really more about me than the homeless person. I’m not sure either decision leads me to a greater sense of compassion for those around me.
The more I am involved in this work, the more I see Jesus cutting through my motivations like an expert surgeon determined to get to the cancer inside. Most of my life, I settled for comparison. I’d walk away from an experience with someone in poverty and be really thankful for having so much.
Just imagine if you and I were getting out of the car on our way to the grocery store. My four year old son, Sawyer was in the back and as we were piling out of the car, he accidentally slammed his finger in the car door. I stop and see him in pain, crying for help, and look to you stating confidently, “Wow, aren’t you glad you’re finger isn’t in this door? I don’t know about you, but I’m so thankful all of our fingers are working.”(1)
You’d probably look at me like I was crazy. Quit being so thankful and help your boy! And you’d be right. See, there is a giant chasm between comparison and compassion. Compassion is a deep awareness of the suffering of another coupled with the wish to relieve it. My friend Scott calls it a bitter pill we choose to hold in our mouths, taste, and then swallow. If my compassion is not growing in an interaction with a homeless person, something has gone wrong.
Have you moved beyond comparison?

3. Did I Notice Jesus?
I know this can sound trite or some kind of platitude for the holidays but I actually think it’s true.

“‘Lord, when did we see you hungry and feed you, or thirsty and give you drink? And when did we see you a stranger and welcome you, or naked and clothe you? And when did we see you sick or in prison and visit you?’ And the King will answer them, ‘Truly, I say to you, as you did it to one of the least of these my brothers, you did it to me.’” (2)

When I take time to discover Jesus in the eyes of homeless people, everything changes. I no longer feel like I’m some hero offering up inspiring charity and I start to feel like the one that is poor.(3) Finding Jesus humbles me terribly. My exchange feels less like a guilt trip and more like worship.
If you ask most homeless people, they will probably understand the gospel better than you do. This is partly because they’ve had countless people preaching to them on the street over the years and partly because they’ve experienced God in ways we’ll never quite understand. Jesus kinda has a reputation of showing up in the least expected places. Who knows, you may be the one walked away blessed.
Has he surprised you lately?

Did I Learn Their Name?
I’ve learned this year at the Mission, it’s never just a housing problem, or a hunger problem, or an addiction problem. It’s always a relationship problem. This forces homeless people to cease to be problems to be solved and they become people to be loved. Sure those other needs are relevant but they are merely symptoms. The disease is a lack of relationship.
The reality is, God may not be asking me to bring a homeless person home and begin a longterm relationship with them. However, it’s amazing how simply shaking someones hand can restore some dignity. It’s remarkable how looking a homeless person in the eye can restore value. Even merely learning their name can reclaim their worth. One time I gave a homeless person a hug and some money and after the tears in their eyes, I’m convinced they needed the hug much more.  I will never care for the marginalized until I create margin in my own life. If I’m not interruptible, I will never hear. If I’m not willing to be inconvenienced, I will never notice. Busyness is the enemy of compassion. I must not merely stop at the obvious physical need but move beyond to the more costly and transformational need of love.
In what small way are you addressing a homeless person’s relational need?


  1. This illustration was borrowed from our awesome President of Seattle’s Union Gospel Mission, Jeff Lilley. He leads the entire organization to greater compassion every day.
  2. Matthew 25:31-46
  3. Matthew 5:3 “Blessed are the poor in spirit, for theirs is the kingdom of heaven.