Updated: May 14
Anxiety is often the worst part of challenging times. As the hours approached and I asked friends for advice it finally dawned on me, I felt anxiety as I realized how dumb it was to voluntarily go homeless for 48 hours. To be clear, it is not dumb to be homeless and Bobby and I are not dumb people for the most part. What is dumb is we were stepping into a world that has different rules and I didn’t know them. I came from a lower-to middle class family and had financial help from my grandparents when times got rougher. I went to private schools and frankly have been blessed my entire life. I am smart, physically capable, and have a lot of life experiences, however homelessness was never one of them. As we walked down in Bayview, I honestly wanted to turn back. I did not want to start pan handling for money. My ego still had a strong grip on me and a series of questions was running through my head: What if somebody I knew saw me? What would they think? These thoughts solidified the reasons I needed to do this. Through a good life, I had become egotistical and soft. I need “scary” things like this to shift my perspective and forge me as a person. THE SCOOP I think it should be noted that I did this with Bobby H, and thank God I did. That said, this adventure will be told from my perspective, as I am sure he will also write about this experience. Here is the scoop: I had on a pair of old tennis shoes, jeans, a beater, baggy long sleeve t-shirt, and a baseball hat. I carried a satchel because Indiana Jones carried one. Inside the bag was a sweatshirt, a sharpie, some torn up cardboard, and a deck of “never have I ever” cards that I found and thought would provide some entertainment. I brought no money, no cards and a cell phone that was turned off the whole time. I decided I wanted my experience to be as legitimate as possible and as thus I chose not allow myself to use any city connections. We stayed away from places I would know people. THE FIRST NIGHT The first thing that we did was tried to pan handle in the street to get money for dinner. This is a mighty embarrassing thing to do. Almost everyone refuses to look and the majority of the ones who do have a judging scowl on their brow. We tried for about an hour and made a combined $0. I did however get a nice young lady who rolled down her window and said “Man, you are way too cute to be out here. I’m gunna get you a job.” She then drove away, but at least she acknowledged me. Then, we decided to try and do odd jobs at restaurants in an attempt to earn a sandwich or some other food. Every place that we went into the workers said they weren’t allowed to give anything away. It was as if the fact that we were willing to work for it didn’t even register. Apparently, that really didn’t matter. We found a big fountain and scoured it for quarters. This gave us a good laugh as we wondered if anybody even throws quarters in fountains for wishes anymore. Next step, we decided to walk into a bar, thinking perhaps we could take out trash for a drink. A couple blocks from the unlucky fountain there was a little bar I had never heard. When we walked in I Immediately saw a man in his underwear who was packing some “heat”. It was at that moment I realized that we stumbled into a gay bar. Hindsight being 20/20, we realized we probably could have just charmed the men to buy us drinks instead of giving ourselves away that we were homeless. Luckily, the bartender was nice enough to give us a couple of to go glasses of water. While leaving we got cat called which was a nice boost for the already damaged ego of earning a whopping zero dollars. As it started getting later in the night, we realized we still had no idea where we were going to sleep. We wandered aimlessly to an area we had never been and stumbled across one of the luckier things that would happen all trip. Down by the UWM School of Freshwater Sciences and the Milwaukee Metropolitan Sewerage District, they had already set up for some sort of festival that was most likely happening the next day. They had rented a portable bar that was made out of a railroad street car. This portable bar was open and would block us from the wind, which was pretty brutal that night. Now that we could check off where to sleep for the night, we focused all our efforts on a food plan. I had gotten a hot tip that perhaps pizza hut throws out pizzas at the end of the night. We started walking towards the nearest pizza hut which was a couple miles away. It had only been a few hours, but constantly walking and worrying about food and shelter starts to wear on a soft guy like me. I own a car so I never have to walk long distances on any sort of a regular basis.
My cardio comes from Brazilian Jiu Jitsu and there is not a whole lot of walking in that. On the way to Pizza Hut we stumbled across a Little Caesars. A light came on in Bobby’s head. They make Hot and ready Pizzas and unless their par levels are perfect, they are going to have some waste at the end of the night. This stroke of genius lead us to possibly the most fun adventure of the experience.
TRASH PANDAS Let me set the stage. It was about 10:30 at night and Little Caesars closes at 11:00. We casually walked by to see if they had any pizzas available and we were in luck. We saw roughly five in their warmer. Surely, at minimum, they would be throwing away a couple pizzas. We waited until about 10 minutes to 11:00 to go in and make our move. We walked into four employees sitting around, eager to get of work and head home. Bobby and I politely introduced ourselves and went on to our sales pitch. We told them we had no dinner and were sleeping on the street. Then we asked if they would have an extra pizzas that we could have after close. I mean they were just going to throw them away anyway right? They looked around the room awkwardly until one answered, “we can’t give away any free food.” I understood this so I followed up with “I understand. What do you do with those extra pizza’s? Do you throw them out?” The response we got was shocking to me. The Little Caesars manager responded, “We wait to throw them out until tomorrow morning.” This moment was super disheartening, because it basically meant that they would rather food go to waste than care about us. I should take a second as an aside for people that don’t know me. I have owned seven different bar/restaurants and five different cafes. I understand why these policies are in place from a business aspect. That said, when it’s you that is hungry and somebody goes out of their way to make sure you can’t eat any food that is already made it really sucks. That knowledge however lead me to think they were lying. They wouldn’t just leave pizza on the ground in a bag because of what it would attract It was also unlikely that they would waste refrigerator space with dead pizzas. So, we left the store and our stake out began. We circled the perimeter of the strip mall and figured out which dumpster was theirs in the fenced in area around back. We then surmised that they would probably take about thirty minutes for closing duties. So, we sat and waited, waited and hoped that they lied to us. While behind the strip mall, Bobby found a garden. Excited for some food, he grabbed a large piece of fruit off the ground and brought it over to me. “Look, I found a coconut!” In all fairness, it was very dark, we were starting to get hungry and tired. Even with those variables I knew there was zero percent chance that we stumbled upon a coconut tree in the middle of Milwaukee, Wisconsin. I grabbed the “coconut” and quickly identified it as a cantaloupe. As I said before, Bobby is a smart guy, but in this instance he supplied me with a hearty laugh. I put the cantaloupe into my bag and we continued to watch. The hunt continued as we moved back in front to watch and see when the employees left. We hung out in a tree at the back of the parking lot like we were hunting deer in northern Wisconsin. Quiet and stealthy, we waited for all employees to leave and the lights to go off. Finally the last person left and we started towards the dumpster with our fingers crossed. I got to the dumpster, opened it up and felt jubilation that there were multiple edible pizzas with a timestamp. We could even pick out our favorite types! Cold, Little Caesar’s pizza never tasted so good. FIRST NIGHT OF “SLEEP” Our journey then continued back to the street car bar we found. My feet hurt so I was excited to get some rest. We got back to our designated place of rest and hopped right in. It blocked about eighty five percent of the wind, however the “windows” were constantly banging from all the wind. It was very loud, the floor was hard wood, it was drafty, and neither of us had a blanket or the appropriate clothing. Frankly, we froze. Between shivering, the lack of comfortable surface and the wind banging the windows, it was miserable. We didn’t sleep, instead took consecutive little naps until about 7am. While this might sound like it sucked, it was better than what loomed ahead of us the second night. It was safe and out of the wind for the most part. HOMELESS TIME (HT) Boredom is one of the hardest things to deal with. In my blessed real life, I am always working on something and always connected. During these 48 hours my mind didn’t know what to do. From this boredom, Bobby and I developed a theory we called Homeless Time. For every minute that passes while homeless, it feels like four minutes from our real lives. Our perception of time slowed tremendously. Saturday afternoon I saw a clock that said 4:00. I realized that we still had over half of our time to go and a frustrated feeling came over me. How could I be so sore, so tired, and I haven’t even been homeless for 24 hours! MASLOW’S HIERARCHY OF NEEDS Part of the reason I do challenges like this is because my current business in personal development field. I believe that we learn through experience and action. I would never have guessed the mental impact that dropping down the Hierarchy of needs has on your cognitive ability. This was one of the biggest eye opening things that I took away. Finding shelter, food, and water takes up mass amounts of your bandwidth. While time seems to go much slower, the things that you think about drastically shift. As we started our Saturday out, we knew that we needed to find different shelter and we definitely needed some blankets to keep warm. It took virtually all day to accomplish these two simple goals along with getting food. HOMELESS CAMPS When we left our Friday residence, we decided to follow the train tracks instead of main streets for no other reason than neither of us had ever done that. What we found was very interesting. There are homeless camps all along the train tracks and people have made makeshift homes inside the greenery. While some just looked like piled messes, others were very deliberate and relatively nice. One person’s place was complete with a tire swing, books, and a tarp. We learned that the idea of “homeless people” extended far past our biases of them. A lot of them try to thrive in the environment that they are living in. As we walked, we thought that perhaps we could score a cheap blanket at a Goodwill. The word cheap however is another very relative statement. Having had trash panda pizza for breakfast, our bellies were full to move on to getting the blanket. We got to Goodwill after a long walk and looked at the prices: $2.99 for a very thin small blanket, $7.99 for a warmer bigger blanket. At this point we had a made a solid twenty five cents, so these prices seemed outrageous! I realized that we needed to change our approach. Instead of asking for money, I asked specifically for a blanket and emphasized we did not NEED money. The results of this switch were positive. We still got ignored by the vast majority of people as we simply smiled and said “hello.” However, one nice lady named Miranda smiled at us and asked if that’s all we wanted. Her smile was everything that is right with the world. She wasn’t ignoring us, she treated us with respect and dignity. She said she had a blanket in her car she would give us. It was large and of medium warmth. I got a bit emotional as it really moved me that she just gave us this blanket. As I write this, I am still smiling about how nice she was to a couple of guys who appeared to be down on their luck. After scoring the blanket, we could go back to trying to find food. We decided to head to Noodles and Company and see if people would give us their leftovers. On the way, Bobby struck up conversation with some college guys who gave us a Busch Light. It's not normally my drink of choice, but in this scenario it only seemed fitting. Once at noodles we used our new technique of direct signage and created a “LEFTOVERS” sign. While we sat for over an hour and got no food, an eat streets driver named Adam, gave us two dollars. Again, the feeling of exuberance was amazing. In my normal life two bucks has never been an impactful sum of money. Out here, he just octupled our entire earnings. The problem was that we still didn’t have enough for food.
THEN I REALIZED I WAS AN ASSHOLE Fast forward a few hours of more walking with sore feet and ankles and we end up outside of whole foods. Surely people who are willing to get that sweet organic cucumber will be willing to help us. Boy, were we wrong! Outside whole foods was one of the worst experiences from a mental aspect. People would not even look at us and the ones that would acted scared. Families would even hide their children. It got to the point that after saying “hello”, and getting ignored, I calmly said, “there is no reason that you have to be afraid of us.” If you are still reading this and wondering what you can do to help, the most basic thing is acknowledge the homeless. Understand that they are people as well. If you don’t want to give them money, food, clothes etc., that’s fine. At minimum, treat them like a person. Look them in the eyes and say “Not today” or “God Bless” or if you have a second “How is your day going.” It was outside Whole Foods that I realized that I have been an asshole to the homeless. I didn’t acknowledge all of them, probably only half. From now on, I will at least say hello and acknowledge them as fellow human beings. MCDONALDS IS NUTRIOUS? As I am sure you guessed, Whole foods was a complete bust. Considering the exorbitant prices of their groceries, it didn’t seem as if people had money to spare so we decided to go where the real money is…McDonald's. There is something about begging for food outside of a McDonald's that is very humbling. Judging by the people walking in, or going through the drive through they were at McDonald's for the price, not the incredible burgers. As humbling as this was the fact of the matter is it was getting later in the day and we had no food and needed shelter still. We continued to get ignored by most, including a lot of college kids who would go out of their way to not encounter us. I am not judging just very interesting as you think of college kids as open-minded liberal thinkers. After standing in the wind, cold and repeatedly getting rejected, an incredibly nice man named Hasani came up to us and asked if we wanted food. We eagerly said “yes,” and he said, “come on then.” He was a calming presence who I bet has bought food for others countless times before. He didn’t ask why or what choices had led us to this awful place. He just had a loving frequency that he lived on and said, “get whatever you want”. Not wanting to break the bank Bobby and I both got two double cheeseburgers. Bobby got his with just ketchup, which I guess indicates beggars can indeed be choosers. Hasani was on his way right away and Bobby and I stayed in the McDonald's for about two hours. We used the time to plot where to stay the night and playing with the never have I ever cards I had brought. THE BEACH During the late morning Bobby and I had walked around and sat on Bradford beach to try to pass time. We sat and enjoyed the cantaloupe/coconut Bobby found right next to a tiki hut, which I presume is done for the season. This tiki hut had a fenced in area outside it and it occurred to me that this fence may block the wind and allow us to sleep in an amazing place: waves crashing, looking up at the stars, relatively safe-ish. Seemed like a good idea, so we decided to do that. We got to the beach after it closed and set up shop in our new casa. At first, it was pretty cool. The lake and its waves didn’t disappoint. The wind was a real party pooper, as it was fierce and constant. The fence did break the wind, but not completely and the blanket that we received was not the warmest. On top of that we only had one blanket so we attempted to do the manly thing and sleep back to back. This proved troublesome as we were sleeping on a wood floor again, and we each had to toss and turn. In fact, this situation turned out to be especially awful as the temperature dropped. We were shivering, sand was bouncing off the locked tiki hut and covering us, and we could absolutely not sleep. We both dozed, but when you woke up you knew only 15 minutes had past and you still had 8 hours of freezing to go. I had to tap into my Stoic philosophy roots to get through this. I thought about Viktor Frankl in a Man’s Search for Meaning and conditions that they had. This was cakewalk versus what a human is capable of, however in perspective of what I was used to it was hellish. While I was thinking, Bobby decided to act. He had enough of these shitty conditions and took strong action to get us a better spot. Bobby may or may not have figured out a way into the locked tiki hut for shelter. It was out of the brutal wind, so I sure wasn’t going to object. While it was still cold, and the floor still sucked, and I still had to share a blanket with Bobby it was like a little piece of heaven after the perception of hell we were in. Bobby came up big for us in this situation. While I was happy to get a little sleep, I knew we couldn’t stay in there and insisted that we get out before sun up. OUR TIME IN A GARBAGE PIT Wandering around the eastside, tired and shivering at 5 am is not fun. Its especially crappy when your feet and ankles are killing you from constant walking. We needed to rest more so we went back to the dreaded Whole Foods vicinity and snuck into the heated parking garage, and more specifically into the parking garage’s garbage area. Honestly, as far as garbage areas go it was pretty clean and we were so exhausted so it didn’t really matter. We laid prone so whole foods security didn’t catch us and we fell back asleep, or at least attempted to once again. When I woke from one of my little naps to rotate my hips I looked over and saw Bobby laying face down. I couldn’t have my battle buddy that desperate to find a somewhat comfortable position that he was ok with putting his face down in a garbage area. I woke him up and said we should go to Collectivo. They open at 6:30 and had water at a counter always available. Sitting in a Collectivo chair was better than face down in a garbage pit. THE ONLY TIME WE CHEATED We did this with the purest of intentions and we really wanted to get a feel for what it is like to be homeless. That said, I run an Idea Walk at Collectivo on the lake at 8:30 on Sundays. I did not want to miss this obligation and thought that I could do both things. I did not intend to get food from people that I knew, but when my girlfriend walked in I caved. I asked her to buy us a hot breakfast and she obliged. It was the best feeling in the world going from a dumpster pit to a hot tea and burrito. You world can judge me and my moment of weakness, but don’t judge until you yourself have gone sleepless on the streets for two consecutive nights. THE LIGHT AT THE END OF THE TUNNEL Sunday, after the amazing cheat burrito, there was a light at the end of the tunnel. Our time was almost done. This thought process got me thinking about how hard it must be to not have that hope, to always have the weight of homelessness draped on your shoulders. I became happier knowing that I have my normal life to go back to. Our goal on Sunday was to visit some more homeless camps that we had found or heard about on the way. The most inspiring place we went was a camp that held ten or more people. It was located right off of a river where a street bridge crosses. This community built and took pride in their home. They had their living quarters under the bridge and a general area outside it. They had a garden, which was growing all sorts of veggies and a few tarped off “rooms” with old beat up chairs. They had a barbell for lifting and both the American and Mexican flags waiving. It was evident that his camp took pride in their home. One resident named Oscar, who spoke very broken English, gave us a tour like it was an episode of MTV’s Cribs. The sense of pride that he took in showing us the garden was emotional for me. What seemed to be the oldest member came out from the under the bridge section and said, “hello.” He has lived there for 18 years! That’s right,18 years! These people were friendly and relatively normal. The only really sad thing about this particular camp was the small written memorial to another camper who had fallen into the river and passed away a few years back. They then proceeded to tell us a story about how another man fell in and a guy we were standing with saved him. After spending sometime in this camp, my whole bias towards the homeless shattered. They can be ordinary people with the need to thrive, just like all of us. Now that I have a sense of the weight of homelessness, I can understand how one gets caught in the cycle and can’t get out. We exited the camp and left the blanket that we had gotten the day before. Bobby left his sweater with them as well. They never asked for money and were happy we stopped and grateful to have received something. The rest of the day we did more painful walking around parks and paths. We saw a lot of different “camps” that didn’t have their inhabitants in them. The pain from the feet hurt, but knowing that I could sleep in my bed at the end of the night pushed me through. Around 5 pm we walked in to my place. We were exhausted and dirty. For those that think 48 hours is easy and we just went glorified camping I would like to tell you this: I am a jiu jitsu brown belt, have run multiple tough mudders, triathlons, water fasts, as well as a plethora of other things that I do like this to challenge myself mentally. This was fucking hard. I was absolutely exhausted. Sunday night Bobby text me a map my run of all the places we walked in the 48 hours. It added up to over 35 miles. I certainly didn’t train for that, or the awful sleep, or the lack of good nutrition. I am writing this paragraph so you understand that homelessness is hard and you should have a respect for that. BIG TAKEAWAYS-PERSONALLY Personally I learned a lot from this exercise. First, and foremost I learned that I judge people too often. This “a-ha” moment really came when I was talking to other homeless and when I really considered the heavy weight of not knowing where your next meal will come from. I couldn’t imagine how a child, thrust into an awful situation at a young age could ever get out from that heavy blanket. I also learned that as mentally strong as I thought I was, I am still weak and have not even came close to testing the waters of what I am capable of doing, both physically and mentally. On Sunday, as we were walking around with my feet just throbbing I couldn’t help but think of David Goggins and how much of a bitch I was being. While what I went through would be very difficult for most, I truly understand where I stand on the food chain of mental toughness. I have a lot of work to go. KEY TAKEAWAYS FOR SOCIETY The hardest thing was to feel invisible and inferior to almost everyone that would walk by. If we would say hello very politely, people would look straight down. If we would say have a nice day, people would look down. If we would say literally anything, people would look down. WHY? My interpretation of this is because we value money as an indicator of personal success. We automatically judge a person whose choices (although sometimes not a choice) have lead them into a life of depending on other people. Society often thinks of them as losers, smelly, dirty, likely to have a criminal record, essentially that they are dangerous and a burden on society. That is what I could see in peoples’ eyes as they just stared at the concrete below them. Well, let me tell you society, we all depend on each other ALL THE TIME. You depended on your parents to survive. You depend on your boss for a job. You depend on society for rules and regulation, so that your weak ass doesn’t get killed by a more fit “king of the jungle” type character. You are dependent on electricity, on running water, on grocery stores. You are more dependent than a homeless person. A homeless person on the street is just more psychologically vulnerable. Let me pose this question to you. If North Korea plops an EMP over America and we don’t have electricity anymore, who would be more likely to survive: you or the homeless person you looked down at? For most of you reading this, my guess isn’t you. After having walked 35 miles in their shoes over 48 hours, I know this from experience. I am not advocating a homeless lifestyle, I am just giving you perspective. SO WHAT CAN YOU DO? Be a kind human. I won’t judge if you give money or don’t give money. Volunteer or don’t. Go homeless yourself and see what you learn or just take it from Bobby and I. Donate to Skinny Santas or find out where this article is and read it for free. The one thing that you all should do is walk with your head high, look over at that seemingly homeless person and make eye contact. Smile. Say a greeting. Treat them like an equal. As for me, I am making a public promise to do at least that for the rest of my life.