Seeing the Human Behind the Cardboard Sign

Feb 28, 2024
These days it's hard for me to move about on the streets of the city that I have loved so well and called home for 35 year now. Sometimes I find myself thinking that Chicago has changed so much in the last few years, and other times I think that the things that I am less comfortable with have always been there, but I'm just noticing them more now than I used to notice them. Part of the reason I am noticing more lately is because certain things have found their way into places that they used to previously steer away from. For example, there were almost never shootings in the Gold Coast and the Loop even though they happened regularly in other areas of the city. 

Another possible reason I am noticing more things that make me uncomfortable is because I am a parent now. Keeping myself protected and safe is important of course, but keeping my daughter safe and protected is an inherent responsibility that I hold more precious than life itself. Of the many things that I notice more in Chicago these days, the thing that I noticing the most is the huge number of people on the streets asking for help. Each time I go to my local Trader Joe's, I see a minimum of four or five families sitting somewhere in or near the parking area holding cardboard signs asking for assistance. I struggle with the fact that I can't help more people than I am able to help. It makes my heart hurt in ways that I prefer not to have to experience. Maybe I need to experience this though, << Test First Name >>? 

Then there are those parts of me that actually shame myself for being uncomfortable with having to look at so much hardship on my playing field of life. Who am I to complain about being inconvenienced by having to look at things that make me uncomfortable as I drive around in my comfortable SUV and return home to my safe apartment in a "good" neighborhood? As hard as it is for the families living on the streets of Chicago, I can only imagine how much harder it must have been where they came here from. 

I also think about what is going on in places like Ukraine, Gaza and many other places around the globe where families are struggling to have access to simple, basic needs like shelter, water and a place to exist without the threat of bodily harm present in their world 24 hours a day, 7 days a week. I have had the privilege of a relatively easy and carefree life compared to most, yet I struggle with my own fears and challenges. It's all enough to make me never want to leave my house again, but then I need groceries so I go to Trader Joe's or I need to work my shift at Joe's, so I take the train downtown and have to look at things that make me uncomfortable again and again. 

Over time I find that I can get de-sensitized by it all and I stop looking at the faces of the people behind the cardboard signs who are asking for help. It's strange to me, because in every other aspect of my life I tend to show up as someone who welcomes the opportunity to sit with others and see their struggles with them. It happens in my coaching relationships. In happens in the multitude of men's community work that I do. Why is it then that I have such a tough time looking at families in need on the streets? Is it possibly because many of them are not white like me? Perhaps my discomfort is tied to some degree of inherent racism that I have epigenetically carried on despite my efforts to unpack the systemic patterns that exist in my world.

Anything is possible, but I think the three primary reasons that I am uncomfortable with seeing families on the street are: 
  • I am someone who has learned to tie his own self worth to my ability or inability to carry the burdens of others
  • I realize that I do not have enough resources to help them all
  • If it weren't for the immense amount of loving support I have received in my life, I might be out there on the streets too
So my coping mechanism as of late has been to just stop looking at the faces of those in need so I don't have to feel uncomfortable. If I don't make eye contact then I don't have to deal with the emotion of seeing hope in their eyes, only to have it dashed when I walk straight by without offering any resources or even a smile. The funny thing about coping mechanisms though is that they work for a while, but eventually the stuff inside you that makes you uncomfortable must come up to the surface and be processed or else it eats you up. One of my ways to process big feelings is to write, so here I am. 

I haven't always been a person who looks away from people on the streets in need. In fact about ten years ago, I met a woman living on the streets who changed my life. Her name is Kelly and she continues to loosely be a part of my life to this day, not because of anything in particular that I did, but rather because of what she did to teach me about trust, perseverance and love. 

One day while leaving work at Joe's downtown, I walked by Kelly as she stood on the corner of Grand Avenue and Wabash holding a sign that said something like, "Trying to raise money for bus fare to California so I can find my family." In my years in Chicago I have encountered thousands of individuals on the streets asking for help. On rare occasions I have handed out a couple of buck or maybe a five, but the VAST majority of times I have been asked for money I have either ignored the ask or said something like, "I don't have any cash on me." Something unique about Kelly caught my eye though. She had a little rollaway suitcase. She stood less than five feet tall. She looked to me like someone's little sister who had run away from home, but then regretted her decision and decided that she wanted to go back. 

I originally walked right past Kelly without pausing, but a little voice inside me told me to go back and ask a few questions. The word "family" on here sign pulled at my heartstrings, so I grabbed a $5 bill out of my pocket and walked back to her and decided to ask her a few questions. I asked her about her family and how she wound up in Chicago if she was from California. Kelly told me that she had run away from a foster home in California where there were abusive parents and that she had some step brothers and sisters. She was hoping to find some of those step siblings and reconnect. She also told me that she had wound up in St. Louis living with an abusive man who stabbed her in the neck with a pair of scissors; she even showed me the scar on her neck. Kelly showed me her bus ticket that had already expired and said that she needed $20 to change the ticket so she could return to California to try to find her family. 

After a five minute conversation, I put my $5 bill back in my pocket and grabbed a twenty. I gave the money to Kelly with an invitation to email me when she reached her destination. I told her that I would be happy to send her some books that I like about the power of thought and how to create your own reality with action and intention. I promised her that I wasn't trying to sell her on any religious ideology, but if she like to read, I had a good library that I would be happy to share with her. In retrospect, I recognize that a part of me that was feeding my ego by trying to be a hero, but I also legitimately wanted to help. Kelly took the money along with a business card with my contact information. I figured there was a really good chance that I would never hear from her again, but I remained hopeful. What happened next began an odyssey that I never could have predicted. 

The next day I got an email from Kelly telling me that she went to the Greyhound bus station to change her ticket and found out that she the ticket was not eligible to be changed and that she would never be able to save up enough money to buy a new ticket so she wanted to know if I wanted my $20 back!  I was blown away. Not only was I not expecting to hear from Kelly again, but there was no way I thought she would offer me my money back. 

I'm not sure exactly what happened next because there so many nuances to the story of our journey with Kelly, but I do know that we started to meet up once every few days in the area near Joe's. After a few meetings, Kelly was comfortable enough with me to let me take her to Big Bowl for a meal. It took a little time for her to see that I wasn't some creep who was looking to take advantage of her. While we sat in Big Bowl, Kelly told me what it was like to try to make enough money on the streets to get a room once in a while and buy some food.

I have no idea what prompted me to try to give her advice as to how to ask others for help, but I suggested that she try to engage more people in conversation and smile more often. As I think about now, I feel a ridiculous to have pretended to know how to be better at panhandling than someone who had actually survived on the streets, I guess that I was just enthusiastic about helping, AND there was that part of me that still wanted to be the hero. I have been dealing with that hero part of me for my whole life. Sometimes it shows up as a good samaritan and at other times it shows up as a shadow part my inner people pleaser. 

A few days after our lunch at Big Bowl, Kelly met up with me and excitedly told me that she had made more money begging in one day (her word not mine) than she ever had before and that she credited me with coaching her on how to look at people, engage them in conversation and smile. Boy did my ego and hero parts love that little affirmation! Kelly then asked me if I would be willing to hold her money for her until she saved up enough to get a room in a house on the west side of Chicago. She said if she had it with her she would be too tempted to to spend on food of for one night in a motel. She was hoping to resist those temptations and save up enough for a deposit on a room for a month so she could get a fresh start. She then proceeded to tell me that she knew a man who had a room that she had rented previously and that she needed to get $250 together to rent the room again.

I talked it over with my wife Christiana and we decided that we would give Kelly the money to get the room right way so she could get off the streets and then she could pay us back over time as she got her feet underneath her. We gave her one caveat and that was that she had to meet us at the house so we could see the room and meet the man she was renting from. Only then would we give her the money. By that point I was feeling a bit protective of Kelly and wanted to make sure she wasn't being take advantage of. Kelly said she was embarrassed for us to see the place because it wasn't in a good area, but we told her that we didn't care and that we wanted to see where she was going to be. 

So on a Saturday afternoon, Christiana and I met Kelly at a home in the Garfield Park neighborhood on the west side of Chicago. I felt VERY uncomfortable as we got closer to the address that she gave us, but when we got to the home, we met a decent man named Steve as well as his mother and Aunt. They had lived in the home for decades. The street that the home was on was a single block of fairly well maintained houses in an area that was otherwise overrun with vacant and dilapidated buildings. The bedroom Kelly was going to get was a tiny room on the second floor. All it had it was an old mattress lying on a dirty floor. We paid Steve the $250 and he gave Kelly the keys. Her smile was worth every penny and a whole lot more. I'm tearing up as In write this thinking about what it felt like to see someone who had been homeless be handed a key to a place she could call home, regardless of what kind of neighborhood the place was in or what amenities it might come with. Stainless steel and granite? Not a chance! This was a roof and a mattress and nothing more. 

At that point in time, my wife and I were very active in Mike Dooley's Infinite Possibilities community. In fact that book  was one of the many books I wound up sharing with Kelly over the next few months. We traveled to three of four conferences a year, with Mike and the group fro IP, often speaking and serving as weekend leaders. We decided to reach out to some of our network of friends and share Kelly's story. Nearly everybody wanted to help. We started a GoFundMe page and ultimately raised over $3000 to help cover Kelly's basic expenses as she started to create new possibilities for her future. We even called the GoFundMe page Kelly's Bridge as a symbol of the bridge to a new life. 

One of the expenses that the money helped cover was Kelly's seizure medication. I was managing Kelly's money and giving her what she needed as she needed it. She had no recent banking history and no ID with a permanent address so we had not yet gotten around to helping her open her own account and there was no way she could be wandering around with cash on her person. Christiana and I were preparing to leave town for an IP conference that summer so I got Kelly a debit card for the account the GoFundMe page was tied to so that she could access money on her own while we were gone. Up until that point Kelly had no idea how much money there was in the account. While we away at the conference Kelly called me and told me she had a medical emergency and that she needed to withdraw some money from the account. I told her to do what she needed to do and that ultimately it was her money, not ours. That was that last I heard from Kelly for the rest of the year. She took all the money out of the account and disappeared. I was devastated. At that point Kelly had become like a daughter or a little sister to me. I created the story inside my head that she needed me and that I was helping her fix her broken life. Ultimately, it wasn't so much that I felt betrayed, but rather It was more a matter of the fact that I missed our daily interaction. I was sad. 

Many months later, leading up to the Christmas holiday, I got an early Christmas gift in a call from Kelly. She was in a hospital in the western suburbs and had apparently had a stroke. Kelly apologized profusely and told me that when she saw how much money she had access to that she decided to do something she had always wanted to do. She took the money and went to Florida to be with her daughter who was living with another family because Kelly couldn't take care of her because Kelly had been addicted to heroin for years since she was 16. Kelly was actually in her mid 30s. I thought she was in her early 20s. I was stunned. 

Needless to say I was overwhelmed on many levels. The first part of my overwhelm was joy to know that Kelly was okay. Another part of me was overwhelmed with gratitude that Kelly cared enough about me/us to call us from a hospital bed and share her truth. There were also parts of me that were angry and felt taken advantage of. I have since learned that it is okay for all of these emotions to co-exist at the same time and while it can be confusing, to try to push down or mask any of these parts of me that had differing emotions is only stunting my own healthy processing. 

I can't possibly recount all the chapters and nuances of my story with Kelly in one already way too long blog post. There is a much longer story to my journey with Kelly and someday Kelly and I hope to tell it together. She is actually a terrific writer and can write brilliant and inspiring prose when she isn't paralyzed her PTSD and ADHD, two labels she has carried as a scar from a lifetime of immense challenge on the streets. For the purpose of this piece of writing though, I think what I want to leave you all with is a short list of just a few of the many things that Kelly taught me about life that I never would have learned if she had not emailed me and offered to give me my original $20 back. Here they are in no particular order, and they barely scratch the surface of the lessons she has inspired me to learn: 
  • The cycle of homelessness is relentless. Once you are on the streets it is nearly impossible to break the cycle because without an address you can do almost nothing
  • A persons actions are not always representative of who they are in their heart. The true Kelly is the person who offered me my $20 back and not the person who took the money and ran. Her choice to take the money was driven by her hopes to reunite with her daughter and create a new life
  • Every addict on the streets is somebody's daughter or son that at some point had a wound that felt like it would never heal. The tipping point into the cycle of addiction is a razor thin liner that I have walked on in my own life and if a few things had gone differently, I could have been there too
  • If you want to help others, it's a good idea to check in with yourself and figure out which of your own needs you are trying to fulfill. While my intentions were good, I had a desire to control Kelly's life and fix her because deep down inside I had so much fear about how little control I actually had over my own life 
  • And most importantly I think, that there is a human with their own unique life story standing behind every cardboard sign. Even if there is little you can do in terms of money or time, everyone deserves and can benefit from a smile, some acknowledgement and energetic kindness

So starting today I am going to start going through my city with my eyes wide open again. My hope is that instead of living in fear of what I see that I will be a beacon of even more kindness on an everyday basis. I'm thinking back to a moment in December when I was so moved by the holiday spirit that I did stop and take notice and I bought some presents for the children of families that were asking for help in Lincoln Square. That's who I am inside, even if at times I have had to look away to protect my energy. If you missed that story about the Spirit of Christmas Present or if you want to re-visit it, you can find it at the link right here.

Well that's all for this week. I think I'm going to give Kelly a call. I haven't talked to her for about a year and it's high time I gave her a ring and said thank you again. In her own special way, Kelly has taught me as much about love as anyone I have ever met on any of the streets of life. 

Love and blessings,

Jim

 

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