Downtown Chicago with Ms. Brenda

Most people have encountered a homeless person at some point in their life.  Maybe the person was on the side of the road, at a stop light, with a sign.  Maybe the person was sitting at the entrance to the Metro.  Maybe the person was sitting on the corner of a street in a wheelchair.  Maybe, you’ve seen all three scenarios; all in the same day.

How do we react when we see homeless people?  Many of us pretend to not see them.  Many are afraid.  Some of us want to do/say something but don’t know what to do or how to say it. 

I am not here today to criticize or to explain away moral obligations. 

I spent yesterday in downtown Chicago with a group of people.  Our sole mission was to give out packages to the homeless and to pray with them.  You see, Chicago is about to get hit with another Arctic blast.  The temperatures here will be at zero and wind chills in the -30s.  If you’ve ever been to Chicago, you know it is always windy and with an arctic blast, the wind gusts are 30+ mph.  These temperatures could easily kill those that have no shelter.

So we got our packages ready and headed down to Chicago on the Metro. 

I’m not going to regale you with the stories we were told or with the experiences we had.  We all know what the homeless face.  We all know that some are there because bad things have happened to them and others because they did bad things.  So what is this post about?

After we were done, the group discussed why so few people come to aid the homeless. It occurred to me that a lot of the reasons we gave boiled down to one thing: ignorance.  Many have fear, but the fear is based in ignorance.

So I want to address some of those for you and to explain ways to overcome.  Maybe you aren’t afraid but you just have no idea what to do or say.  I will go over that too. 🙂

Let’s face it.  Many of us are afraid of being attacked.  There are reasons that homeless people are homeless.  Some of those reasons include criminal activity.  I am not going to tell you that this is not real.  It is.  However there are ways to mitigate this. 

  1. go in a group – do not go alone.  This should be obvious, but there is safety in numbers. 
  2. stay above ground – that may sound funny to many, but if you live in a major city, you know that often times the city has layers of roads.  Stay in the areas where most of the foot traffic is.  If you notice that there aren’t many people around, change your location to a place that has more foot traffic.  This is important for your safety.
  3. go in daylight during a busy time – choose a day where people are in the city.  Go when it is daylight and don’t go in areas that are not lit properly. 
  4. do NOT take money – best practice is to not even have it on you.  Keep a credit card in your pocket and that’s it.  When you are asked for money, you can legitimately tell them you do not have any on you.  This will eliminate any need for fighting. 

Mental Illness
Many of us do not know how to deal with mental illness.  It is a scary thing, sometimes, to face.  Unfortunately, the mentally ill are often homeless because their families won’t or can’t pay for their care.  Often, wards of the state are turned out.  There is no way to avoid this possibility.  But here are some reassuring things.

  1. not all homeless are mentally ill – many homeless are not mentally ill.  Society has taken steps to try and provide for those that are mentally ill, resulting in fewer being on the streets.  That does not mean you won’t run into someone though.
  2. they are God’s too – remember, God created all.  Treating the mentally ill with kindness will usually result in a calmer time with them.  This is not always the case, but it never hurts to treat them with kindness just like everyone else.
  3. groups ensure safety – sometimes, a mentally ill person can be violent.  However, by going in a group, you can significantly decrease any problems associated with this. 

The biggest obstacle we face is fear.  It is mostly fear of the unknown.  What do I say? How do I talk to them? What if I offend them? It goes on and on.  Let me set aside some of these.

  1. What should I say? – say whatever you want.  Here’s the thing, they know they are homeless and many will even truthfully tell you why they are.  Ms. Brenda in the picture explained to the kids that she was there because she didn’t listen to her mom, got in a gang, started drugs, etc.  She was able to get her life together, but couldn’t manage to keep enough money around to get a home.  She was very straightforward.  When we asked what she needed, she told us. There was no awkwardness.  We either had what she needed or we didn’t.  We asked her if she would like us to pray for her.  She said yes.  Others have told us no.  Respect their wishes.  The take-away here is that the homeless are less pretentious than the rest of society.  So while your co-workers may lie about their lives, pretend things are fine or try to manipulate you, the homeless usually just tell you straight up when you ask.  So just be genuine.
  2. What if they ask me for money? – many people do not want to give the homeless money because they don’t want to participate in their vices.  This is a legitimate concern.  That is why you should go without any money.  Have a debit/credit card on you and your ID, but leave everything else at home or in your car.  You can legitimately say you don’t have any money.  An even better way of saying this is something along these lines… “I don’t have any money on me, but I do have ______________ things.  That is why we are here.  To pass out _________ to those who need it.”  This leaves it positive but also sets the boundaries of your generosity in a polite way. 
  3. What if I offend them? – this is easy.  Just say that.  Often times you may want to ask something or say something that you aren’t sure if it’s offensive.  So say it.  “I don’t want to offend you, but would you mind if we pray for you?”  Believe it or not, sometimes people are offended by prayer.  They will tell you if it is.  One person told us it was offensive to him for us to pray.  We respected his desire.  But then it’s awkward right?  So just move the conversation forward. “Well here is our Christmas gift to you.  We wish you a very Merry Christmas.  Please take care.”  The homeless understand your generosity and they understand they need it.  Offense is usually not an issue. 

So if you see a homeless person and want to do something to help, do it! It will be greatly appreciated.  Do you have more questions? Something I didn’t address?  Leave me the question in the comments!  Let’s all work together to share love. 



  1. Loved your commentary. I think it addressed many issues regarding the homeless. Bottom line is, they need help so if you can, do!

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