The Eclectic Path of an Outreach Worker: Reaching Out to Those Experiencing Homelessness!

I love my job! 

I hate I have to do it! 

I wholeheartedly believe that housing is a human right. Housing saves lives. Housing reduces harm. Housing should be affordable and available for all, and yet, sadly we live in a world where housing is only affordable, adequate and available to some, leaving many people unhoused or living in unhealthy or overcrowded homes. Therefore I have dedicated most of my adult life to helping those who need a place to call home. 

In January 1997, I started my journey in Chicago as a community worker in a large homeless shelter, Cornerstone Community Outreach (CCO). Today, I continue my journey in Tāmaki Makaurau as Visionwest's Supportive Housing Outreach Leader. Whereas my roles have varied over the decades, my emphasis in this piece is to focus on my responsibilities as an Outreach Worker in both cities: what it is, how I do it, and why I think it's important! 

Beginning in 2001, I helped set up and direct CCO's men's shelter, only for it to be closed in late 2004. This decision was made against my wishes! This decision was agonising for me, but it was even more devastating for the 100+ men who used to cram themselves into our cafeteria for a night's sleep. The shelter may have looked chaotic and unhealthy, but it was far healthier and safer for those men than trying to sleep on the Chicago streets or trains. When this forced closure happened, it seemed like the gentrifying neighbours had won. The majority of those poor men were pushed out of our shelter into other shelters or onto the streets once again. 

I recognise this time as one of the most defining moments of my life. It filled me with anger and angst and sparked a fire within me. I felt no one heard me. I felt helpless and hopeless as I saw community groups come together and use their collective voice to spread lies and create false narratives against us and the men. I saw political leaders succumb to these "haters" and their money. I saw the raw emotions of dejected and rejected men face even more dejection and rejection. I couldn’t let this injustice lay dormant, I knew I had to respond. At this defining moment, I redirected my trajectory and began my journey as an Outreach Worker! 

A few days after the city had come and emptied our cafeteria with their half-truths and blatant lies, I remember standing in our empty cafeteria. The eerie silence haunted me. I stood in an area once filled with non-stop noise and energy. The silence was screaming! It triggered me! It was awful! It was emotional! It was painful! I felt anger! As a response, I plucked up the courage and ventured out of the shelter, around the corner and onto Broadway. I wanted the displaced men to know that what had happened was unfair, it wasn't our decision and we hadn't forgotten them. I felt inadequate, I didn't have anything to offer except my words and presence. I felt insignificant, I didn't know where it would lead, but I needed to venture out of my comfort zone and walk into the unknown, so that's what I did...

My journey started by wandering down Broadway toward the shelter where the City had transferred nearly all the men. Within 5 minutes, a fella I knew intentionally fixed his gaze on me, flexed his muscles, left his crew and approached me. He made it abundantly clear that I was in the wrong area and I "best get back to my block". I knew exactly what he meant, but instead of turning around, I kept walking until I decided to cross the street and head back. He kept mean-mugging me the whole time. A few minutes later, I came across another man I knew, he was lying on the ground with a couple of his buddies assisting him. I stopped to see if I could help, but somehow he managed to find enough energy out of his heroin stooper to yell "f*ck off" and then proceed to lecture me how we have never given a "f*ck about him", are fake Christians, and how I need to stay away from him and his people. I walked back to CCO, despondent! It hadn't been a good debut!

I'm happy to say I didn't give in. I went out again the next day, only to be met with positivity. That debut was quite possibly the worst outreach experience I've had in 20 years. And regarding those 2 fellas, our journey didn’t end that day, I walked and talked with them for years after their initial threats and insults. 

That's my beginning. It was ignited by experiencing injustice, and the desire to let a bunch of guys who'd been ostracized, criminalized, and rejected know that they were worthy of compassion, acceptance, and love. I wanted them to know that Jesus welcomes and includes those the world hates and excludes. I wanted to pluck up enough courage to follow his example! 

So here I am, 20 years later! I've had plenty of other responsibilities during this time, but Outreach has consistently been a significant and essential part of my work. My journey has had its hard and painful moments, but it's fuller of all the countless wonderful stories and encounters I hold in my heart.

The primary goal of Outreach is to help those who are not housed find safe, affordable and suitable housing. But, it's so much more than just that! It's not as simple as approaching someone sleeping under a bridge and placing them in a house, it's much more complicated than that. Outreach sees the need and responds, it provides food for the hungry, clothing for those without, helps rescue people from the brutal weather, and so much more! 

And that's what I will elaborate on for the rest of this post...

I am going to highlight 5 areas I have found to be essential for anyone who wants to be an Outreach Worker. I believe Outreach not only helps those experiencing homelessness find safe places to live, but it also has the power to benefit society in general, meet people's needs, challenge injustice, provoke positive change and bring redemptive hope and peace into our communities.

1: Outreach Workers must honour every person’s dignity and uniqueness!

I believe it's essential for anyone who works with those experiencing homelessness to see each and every individual as unique and worthy of housing, food, clothing, freedom and human rights. This is foundational. We shouldn’t discriminate. Without believing that “all deserve a chance”, our practice loses validity. This is an act of courage, as not everyone we come across wants us in their presence and we will encounter people with vastly different (even opposite) beliefs and attitudes to ours. I believe that as a follower of Jesus, each person I come across is a unique child of God worthy of my efforts and utmost respect. 

In my job, I have the privilege of meeting each person on their difficult journeys and often end up walking with them through some very deep and dark valleys where their future looks bleak. But, their stories normally don't end in these valleys. Potential and hope don't normally die in these valleys. I believe Outreach Workers should be in these places helping people see their potential and bring hope for a better tomorrow. Over the decades, I have seen countless miracles and I cherish these stories in my heart. I cling to hope, knowing it doesn't disappoint. 

Some people reading this may be thinking, “You’re naive, you’re too woke, some people don’t deserve your respect because they’re smoking crack, they’re in gangs, they’re criminals, they’re alcoholics, they’re violent, they’re lazy, they’re entitled”. I’ve heard it all! I’ve seen it all! It’s not about denying their struggle, it’s about seeing it, acknowledging it, confronting it when necessary, and still walking with them on their journey. And I’m happy to say, that I have had the absolute honour of journeying with hundreds (if not thousands) of wonderful people who have struggled with countless troublesome complexities, and each and every one of them is worthy of my utmost support and respect. 

2: Outreach Workers must build trusting and purposeful relationships!

Respecting someone’s uniqueness is only the first step, we have to take it further by building trusting and meaningful relationships with those we meet. It’s one thing to say “I love everyone”, but it’s another thing to step into their space and walk alongside them. I’m often reminded of what the Apostle John wrote, ”Dear children, don’t just talk about love. Put your love into action. Then it will truly be love.“ (1 John‬ ‭3‬:‭18‬) Our actions matter!

Almost every person experiencing homelessness mistrusts those in authority, and rightly so! The broken promises, blatant lies and half-truths they receive are never-ending. What rough sleepers don't need are "know-it-alls" who come in with their suits and "too-good-to-be-true" promises, because most unhoused people I know have seen and been deceived by these snakes on numerous occasions. What they also don't need are people coming in with their "it's my way or the highway" elitist attitudes. What those experiencing homelessness do need is what we all need, empathetic, non-judgemental folk who are patient, compassionate and forgiving. We need those who will listen to our needs, hopes and dreams and do what they can to help us attain them on our journeys. 

Some reading this will think, "Bro, you're being harsh, they're just trying to help people in need." I don't think I am, I've witnessed some atrocious lies and miscarriages of justice. When the men's shelter was on the verge of closing in 2004, a city-wide leader came and gave an eloquent hope-filled speech about how he will make sure all 85 men are housed. He looked at all the veterans in the room, thanked them for their service and said, "Especially You All!" When the beloved veterans and almost all the men were loaded in maxi-vans and secretly placed in another homeless shelter, most of the fellas shrugged and weren't surprised, because "this is how it always is." I felt for them all, but especially for the few who were still naive enough to hope and believe these promises.

These promises come thick and fast, sound good and tickle people's ears, but only a few come to fruition. As Outreach Workers, we must work hard to change the narrative, because most people we meet will not believe us until they see the evidence. Building trusting and purposeful relationships takes time and effort. The streets talk. They talk loudly. Outreach Workers build reputations. We become known as either trustworthy or fake. Our integrity and honesty are on full display. We need to be humble enough to apologise when necessary. We need to have the love and courage to walk with people through the politicians' lies and speak truth to power. An effective Outreach Worker is known as someone trustworthy and productive because their words and deeds are not on separate paths. 

In other words, Outreach is never about forcing our will on others like colonisers but rather about listening and building trusting relationships. It’s about asking if we can enter on their journey with them and then supporting them on their hikoi. Sometimes they'll say "no" and it means honouring their wish. Our journey with someone may last 40 seconds, 40 minutes, 40 days, 40 weeks, 40 months or even 40 years, and like in any trusting and purposeful relationship, it’s knowing there will be painful or depressing periods, but also knowing there will be moments of celebration and progress.

3: Outreach Workers must network and collaborate with others!

We can be great at building relationships with those experiencing homelessness, but if we can’t create pathways to help meet their needs, our work is no longer Outreach, it's just a friendship. This is why networking and collaboration with others is vital, it creates opportunities, it generates hope, and it helps those who are unhoused find housing! 

Outreach isn’t about being a hero and overcoming hurdles by ourselves, but rather it’s imperative to create connections with those with similar mindsets, missions and goals. Through our togetherness, those in need benefit. Outreach should never be a competition, but rather a beautiful union of people coming together and using all our gifts, talents and resources to create opportunities. 

When we network, it’s good to be selective, it’s good not to waste our time trying to collaborate with those who bring ulterior motives. Too many people degrade and mistreat those they’re expected to assist. It’s imperative to find the right people and connect with them. Those with power and money may look attractive, but don’t be fooled, as they hardly ever make a good connection, those with love and compassion do! Networking should be both selective and non-discriminatory, and we do this by finding and connecting with those who also honour each person’s dignity and uniqueness. 

I network with my coworkers, I network within government agencies, I network with those on the street, I network with librarians, I network with churches, I network with those in other organisations, I network with neighbours, I network with other outreach workers, I network with anyone and everyone whom I perceive cares deeply for those unhoused and in poverty. 

A few months ago, I was asked to assist a man who was sleeping rough. He had recently been evicted. I wouldn’t have found him without connecting with another agency where he often went to get food. I couldn’t have helped him with his paperwork without working with the appropriate government agencies. He wouldn’t be housed today if I hadn’t collaborated with an organisation that is brilliant at housing and supporting those who are chronically homeless. His new apartment was filled with household items and food through networking with many coworkers. This humble man would still be hidden from the world, sleeping under a bridge, if it wasn’t for many people coming together for him, ensuring he is now safely housed. 

4: Outreach Workers must be advocates and activists for those experiencing homelessness!

People are sleeping in their cars and tents tonight because of small irritating holes and giant gaping holes in the system. People are couch-surfing and others are crammed into cold damp garages because housing solutions are few and far between. People are sleeping rough tonight because of discriminating and racist policies. Homeless shelters and emergency hotels are filled with those who’d rather be in their own homes tonight because society is rife with systemic problems that cause homelessness and struggles to provide adequate housing solutions. It all needs to be addressed. 

Blame is often placed only on the unhoused. There are always those who loudly accuse people of not trying hard enough, and that's the reason they're homeless. I'm not denying individual responsibility, because as Outreach Workers, we assess and help people navigate what necessary steps they need to take and then we help them fulfil those goals. What frustrates me is the "pull yourselves up by your bootstraps" mentality, it's insensitive, it's dangerous, and it leads to harsh judgements and denial of how our society is failing the most vulnerable. We shouldn't be yelling at people to "pull themselves up", we should be asking why certain people don't have bootstraps or even boots. 

Some of the hardest-working people I know are homeless. I know people living on the street who have never touched alcohol or drugs. I know people who are homeless because of their honesty and integrity. Many wealthy homeowners are alcoholics, lazy, snort cocaine and rip people off. What people do or don't do doesn't make people houseless, what people have or don't have does. It's easy to judge those experiencing homelessness as having character flaws. It's easy to think "They did something wrong", so that must be the only reason they sleep in their van. It's easier to blame or right off or ridicule an individual than challenge or stand up to a faulty unjust racist system. 

Outreach Workers must have the courage to challenge the systems that cause homelessness and fight for more housing and solutions. We need to use our power and privilege to bring about positive change. We need to be advocates and activists! 

Advocacy means going into governmental agencies and representing the ones we work with. Our voice and presence have an impact. People know that their poverty and race sway decisions when it comes to receiving benefits, getting housed and sentencing. Over the years I’ve had many people say to me, “I wouldn’t have got what I’m entitled to if it wasn’t for you being there” or “Thank you for coming to Court with me, I feel like that’s the first time they’ve ever listened to me.” 

In Uptown Chicago there was a Tent City just minutes from my house. These poor people, even though they were struggling to survive, sparked a fire, they became our neighbourhood's focus point. They unintentionally ignited a political battlefield. The powers-that-be didn’t want a homeless encampment in a gentrifying neighbourhood and certain neighbours didn’t like the view on the way to the lake. They wanted what they called an eyesore to disappear. They wanted the police and City employees to come in, exert their power and shut it down. They didn’t care if those living in tents were successfully housed, arrested, incarcerated, or shoved to another part of Chicago, they wanted them gone, they didn’t want them in their backyard. 

When the City employees came in with their plan to shut it down and their "too-good-to-be-true" promises, those living in the tents needed more than just food and blankets, they needed activists and advocates who would fight for them. I'd seen this propaganda before. I'd seen their sneaky tactics before, where they'd forcibly relocate everyone under the guise of housing everyone. Our goal was to ensure they were safely housed as they promised. Over the following months, we held the City accountable by reminding them of their lofty promises, we advocated for the right housing for the right people, we went to Court and challenged illegal arrests and evictions, we did various forms of protest, and we made sure no one was forgotten. It was damn hard work, it took a couple of years, but we battled with and for them, and the result was, that most of those who signed up, ended up housed, eventually.

If we don’t include advocacy and activism in our practice, our work is incomplete and those experiencing homelessness will not benefit from our privilege and all we have to offer. 

5: Outreach Workers must be flexible and adjustable! 

I'm driving to drop food off to someone who lives in her car, and on the way, I receive a phone call that someone else I work with can immediately move into a place! At this decisive moment, my schedule changes, my priorities change, my day changes, and my focus changes! Many days start with a plan to go down one path, only to venture onto a completely different journey. Outreach Workers cannot be rigid, they need to be flexible and adjustable. 

Outreach Workers must be adaptable enough to flow wherever our journey may take us on any particular day. We must prioritise between what's essential and non-essential. We must decide between what's urgent and what can wait.

A few weeks ago, a guy sleeping in his van texted and told me he was going to end his life, he became my priority for the following 2 days. Last year, I received a call that a woman I'd been assisting could finally move into her long-awaited apartment, my priority was to find her and make sure she had the appropriate paperwork and then make sure she made it to the appointment. When I was requested to assist a father and his 2 children who were getting evicted, I had to drop all my scheduled appointments for a couple of days to ensure they moved into emergency accommodation. 

An Outreach Worker's life is filled with nonstop variety and crucial decisions. Every week will simultaneously contain so much beauty and pain. It's not dull. It's eclectic. It's agonizing. It's surprising. It's wonderful. It's energizing. I have the honour and privilege of journeying with people as they enter their new homes. I also have the honour and privilege of visiting people in the hospital, bringing them clothing and food, attending their funerals, and buying them coffee. I have the honour and privilege of advocating for people in Court, de-escalating tense situations, hearing their beautiful traumatic stories, and encouraging one another. Every day is an emotional roller-coaster, full of unique people with their stories, and it's an honour and privilege to be permitted to hike with them on their unique journeys.

By highlighting these five areas I have focused on the essence and spirit of Outreach. But as a side note, I want to quickly emphasise that in doing this work there are other things, seemingly mundane things, necessary things, that also have to be completed. Paperwork has to be done. Reports have to be submitted. Boundaries must be set and safety plans established. Confidentiality is a must. Meetings will be attended and we have to stay accountable to those who will keep us moving in the right direction. 

Just over 20 years ago I stepped out of an eerily silent cafeteria to attempt something new. I didn’t know where it would lead, but I knew I had to do it, I knew it was important. For just over 20 years I’ve tried to put love into action. It’s an adventure I’ll keep walking, through the valleys, over the mountain peaks, and across the plains…

I remember Johnny...

• I remember first meeting him at the Soup Kitchen I helped run.
• I remember him sleeping under multiple blankets in the entryway to my house in sub-zero temperatures.
• I remember him coming into the shelter with an oversized green trench coat. The bottom was wet because he'd been walking through the snow. He requested something that fitted him and I gave him a beautiful Blackhawks jacket and he gave me the coat. I washed the coat and still have it today.  
• I remember him telling me he’d been homeless since he was about 12 or 13. He would have been in his late 30s when I first met him. 
• I remember praying for him and with him. 
• I remember him loving to ride bikes. He always had a bike and those bikes frequently changed. 
• I remember finding him passed out under a bridge in snowy sub-zero temperatures and bringing him into our warming centre. I remember how swollen his fingers were. I remember how long it took us to warm him up. I remember this happening a few times over a few winters. 
• I remember how he'd hug my daughter Muriwai when he'd see her. 
• I remember sharing communion with him at St. Augustine's for American Indians. 
• I remember networking with other agencies to get him off the streets and into housing. 
• I remember when I discovered he struggled to read or write, but could sign his name beautifully. 
• I remember taking him downtown to get his State ID, as he couldn't do it on his own as he needed it to have a chance of getting housed. 
• I remember vigorously advocating for him when he lost an opportunity due to being arrested for something small and petty. 
• I remember him qualifying for a permanent supportive housing program. 
• I remember him signing a lease and finally getting a place he could call his own. 
• I remember helping him move into this place. I remember his smile. I remember his excitement. I remember him showing me his collection of country music cassettes. 
• I remember him drawing me 3 pictures and gifting them to me. I remember they'd been drawn with crayons, had a little colour and had indigenous themes. I remember hanging his artwork on my office wall. I remember them still being there when I left Chicago and headed to Aotearoa. 
• I remember him losing his place.
• I remember him immediately moving into another place because he was registered in a permanent supportive housing program. 
• I remember the day I heard he had sadly passed away in a park. He was in his 50's. 
• I remember reflecting on his life. I remember wondering what more I could have done. I remember crying. 
• I remember attending Johnny's wake and funeral, saying a few words of remembrance and hugging his relatives and friends. I remember looking at him lying there and saying goodbye with tears in my eyes. Rest In Peace my friend, until we meet again...