Talking to the Homeless and the Theatre of Everyday Life

by Scott - 23 Comments

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Every time I step on a subway and hear a declarative “Excuse me” my ears perk up. I quickly scan the rest of the car to find the eyes of a person who has fallen on hard times. As I rise up from my seat and move with purpose towards the man, I feel the curious gaze from those around me grace my shoulders.  
No words. No hesitation. Just open arms. I go in for a strong 2 second hug. Then I ask him his name and tell him mine is Scott. We usually talk till my stop at which point I make my way to the door. A smile rests firmly on my face as I step off because an explosion of joy has just filled my heart.

Talking to the Homeless
Anyone who has taken the time to truly get to know me on a deeper level knows that I have a heart for the homeless. I try to talk to at least one homeless person most days. It helps me maintain the life perspective I strive for and feels extremely rewarding to have a tangible effect on others. When I started this about 9 months ago it was a bit uncomfortable. Now it’s just something I do.
I started talking to the homeless after I realized that a dramatic paradigm shift needed to take place.

People walk by the homeless everyday and feel good about themselves when they give them a dollar. “Yeah” they think, “I’m making a difference. Did my good deed for the day. Heaven here I come!”
I’m not saying a dollar for a hot meal doesn’t help. It does and I know these people are grateful for it. The problem is that this is a band-aid solution. What these people really need is our time, energy, expertise, and resources. This combination is far more effective at getting them off the street and on to leading more sustainable lifestyles. I plan on writing a ton of posts on this.

For most of us, it’s unrealistic to think we can effectively do our day jobs while devoting our time, energy, expertise and resources to help every homeless person we encounter. So I decided that a good middle-ground solution that I could practice on a daily basis is to just to stop and talk to them for a few minutes. It saddens me that I never have to look far.

Describing these interactions as personally rewarding is a vast understatement. And I’m pretty sure the value chain exists on both sides of the equation. I can’t tell you how many times I’ve heard the phrase “thanks for actually talking to me” muttered. What a sad commentary on the time allocation preferences of our society.

My favorite time to talk to homeless people is on the subway which is why I painted the picture above. On a subway you have a captive audience and exponential network effects exist on the offline world. Within this theatre of our everyday lives, you’re presented with an incredible opportunity to show people what humanity is all about. Without fail, the people that witness these interactions start opening the wallets in the aftermath. It’s kind of funny. Now if I could only get them to shift their paradigm to one in alignment with a more sustainable solution.

I’ll never forget one time following a subway interaction when this wall-street looking guy who probably was wearing a custom suit more expensive that my entire closet grabbed my hand. He looked at me with a tear in his eye and just said thanks. I also will never forget when this Filipino actress/tv host  whose pretty easy on the eyes came over and talked to me afterwards. Yeah, we still keep in touch : ) NBD

I’ve wanted to write about this practice for a long time because it has had an incredible impact on my life. I’m just a better, more thoughtful person.

But until now I always hesitated to share this because there are certain aspects of my life that are sacred. For better or worse I tend to silo these things off from most people. I do this mainly because the idea of drawing attention to them in a way that could be perceived as self-promotional never sat well with me. This is the same reason why I’ve been intentional about being alone when I talk to homeless people. 

I’ve come to realize siloing off these parts of my life is an selfish act. If I share them with others there is a greater chance to have a positive influence on the world around me. This was my motivation for writing this post. If you’re reading this and think otherwise go pound sand. Ultimately, knowledge is life’s richest currency and we should always share it when it can make those around us better. Nothing is cooler than finding out an accomplishment or something cool about someone else without them telling you. However, I liken this to wasting food on the table of making the world a better place.

If one person who reads this takes the time to talk to a homeless person in the next month I’m chalking this up as a win. A Shutout if they do it on the subway.

Man that felt good.

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23 comments, add to the conversation.

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  3. Erin Domingo


    Thanks for sharing this! I got chills reading it. I’ve always wanted to talk to the homeless myself, hear their stories and help them. Reading this gives me the courage to do so. I graduated with a degree in packaging design, and I came across this student project that I wish I had thought of myself. 
    Check it out:



    1. ScottBritton

      Compassion and my belief the position I’ve been put in is largely total luck. We don’t choose our parents. These people got a crappy hand and need those who’ve got good ones support


      1. Darius Tan

        Very interesting – I’ve always believed this about the education we got and the “rules of the game” when going to school and getting a job, but never extrapolated it to homeless people. Nice insight.


  4. Ryan Ridgway

    This post literally made me tear up man! It’s always comforting to hear that there’s still a bit of good left in the world. Call it right or wrong, but I live in the 3rd richest county in America, so it’s rare that I see a homeless man/woman. I do go downtown often though and always “slip them a few dollars” – That isn’t enough though. Thanks for reminding me of the true value of a warm caring conversation. Just curious, what do you talk about when you approach them? I’d assume the nature of some topics would be pretty personal. Thanks – Ridg


    1. ScottBritton

      Wow thanks man.

      I usually just approach them and say “hey how you doing, I’m Scott, I just wanted to say hello.” Then i follow this by “so how long have you been out here” which kind of launches into a personal story from which you can navigate the convo


  5. Edward

    Hey Scott, I’ve been reading your blog for a couple of weeks and this is my favourite post so far. I can feel the internal conflict that you had in posting this, and just want to thank you for sharing.


  6. Cain McCallam

    Sitting here in my cosy bed, in a semi detached house in London i thought to myself what if i were outside right now? my following trail of thought lead me to ask myself why no one talks to the homeless and maybe i should… so like most my thoughts i googled it too see what came up and if anyone shared a mutual thought.. Im so happy i found this article it was truly beautiful and confirmed to me that i should follow in your footsteps! Cain


  7. Post Author Scott

    Cain that is awesome to hear. To be honest, I haven’t been doing this as much as I should, but this comment inspired me to get back on the bandwagon. Let’s do it! I hope you have a wonderful day


  8. Karen

    Hi, Scott!

    Thanks for writing this! I was actually searching for how I can help homeless when I came upon this website. It really helped me, and I would like to thank for that 🙂 It is delighting to hear that there are people like you out there and I hope others will start doing the same.
    I’ve always wanted to help this one homeless who lives near a library I often go to.
    I’m sorry for saying this, but to be honest, what I’m most worried about is the risk of getting hurt by contacting a homeless. This homeless who I want to talk to, lives in a secluded place… so I’m a little afraid 😛 Should I just go talk to him without thinking about any dangers? Please tell me if there is any danger in talking with a homeless person, and perhaps a suggestion on how to approch him?
    Thank you very much!



  9. Post Author Scott

    Hi Karen! I can’t really make a recco whether a particular person is safe to approach or not, but I think you can steal be a servant by simply talking to them and leading with giving food : )


  10. Jim McCord

    Thanks Scott. Great article. I have been randomly talking with homeless people for 12 years. Life changing. I posted your article on my facebook page today. Tried finding you on fb but couldn’t. Try to friend me… Thanks and let’s stay in touch…


  11. Karen Sv

    I wouldn’t start by asking them how long they have been living on the streets, this may embarrass some of them and they have been humiliated enough in this demeaning lifestyle. I would just ask how they are doing and maybe what are their concerns or interests, hobbies and maybe you can actually do something to help alleviate a concern they have( did you see the cop who bought a homeless guy a pair of shoes in the winter because the guy was getting frostbite from holes in his shoes?)- something like this would be truly helpful and wouldn’t take much.


  12. Nicole A

    I just had my first real interaction today. My roommate and I had been talking about attitudes toward the homeless, how we avert our eyes so we don’t feel bad, and how it must feel to sit on the sidewalk all day and watch thousands of people pretend you don’t even exist.

    So today after I grabbed a quick brunch at Panera, I wrapped up that bit of bread they give you as a side, along with a small cup of water. I found a man sitting just off the street corner, and as soon as he saw my intention he started saying, “Oh, God bless you young lady, God bless you!” Then he said, “Hey! What are you studying?” then “Would you sit down for just a minute?” If I left him then, it might have ruined the positive effect of what I had just done. So I sat, and let him talk. He said he had been wanting to tell his story for the longest time. He told me how his family was killed in a car accident when he was 3, how he still doesn’t know how to deal with that. Then he started to recall some of his long-forgotten memories.

    He asked me just one favor, but promised not to tie me to it. He asked me to find which train company hit his family’s car. 15 minute Google search. It’s my plan to print out the newspaper clipping and give it to him next I pass by. A little “time energy and resources” on my part, and yet I made his whole month. The last thing he said after our handshake goodbye was “Don’t forget me!” I shook my head that I wouldn’t, and soft tears welled up as I continued on my way.


  13. Lidia e

    Hey Scott!

    Just wanted to say how random it is to have stumbled upon your writings, but it hit a big chord with me. Ever since moving to NYC a few months ago and always have being a humanist kind of person, it’s been an indescribable feeling seeing and interacting with the outstanding amount of homelessness, but also the opinions that some have about the homeless. It’s just sad how some don’t longer look at them as people, when they dont even have the slightest clue what some of these people have to go through and how their situation puts them in a much harder place to attain a stable lifestyle. I began more and more to break away from the majority and actually lend an ear, engage with them like I would any other being, smile at them and wish them the best and if I have anything to help, I do so. I’ve gotten some to tear and have teared a few times myself. In times I’ve inspired a few but they really inspire me, that we as humans have an endless capacity of compassion we dont always share but when we do can make all the difference even if only in that moment.


  14. Maddie

    I’m 14 and I see at least one homeless person everyday on my walks to and from school. I always try to at least smile at them and acknowledge them, which is more than what most people I know do. I usually don’t have money with me though, so whenever I can’t give them anything but a smile, I feel guilty. I was thinking about how no one ever talks to them, and then I found this article. So my question is this: How do I start a conversation? I’ve got really bad social skills in general, and I know that I would have to be careful what I ask them about, as it may offend them.


  15. Rita

    I’m grateful to have read all of these comments, as you’ve all encouraged me to take the “next step”. If we don’t change anything about our everyday life, we aren’t really moving forward.
    TODAY is the day.
    I’m thankful for the opportunity I have to make a difference today.


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