Loving someone homeless is its own kind of ache, one that rarely gets named, and even more rarely understood. When a person you care about is living in a camp, tucked behind tree lines or under bridges, you carry a unique kind of worry. It’s the worry that wakes you at night. The worry that sits in your chest like a stone. The worry that comes from knowing someone you love is surviving, not living.
Most people see a homeless person and think “stranger.” But for many families, that is someone’s son, a daughter, a sibling, a parent, a friend. Someone who once sat at their kitchen table. Someone who once laughed in their living room. Someone whose story didn’t begin with homelessness.
I know this because I lived it!
There were many times that I was outside on the streets and just minding my own business, when I felt so alone. How was this even possible in a big city with people walking around everywhere? That feeling still haunts me today; it’s an eerie feeling to be in the center of so much going on, yet feel as if nothing is happening at all. I wasn’t asking anyone for anything, wasn’t bothering anyone; however, I was in the same clothes I had been wearing for days, hadn’t showered, and didn’t have the proper clothing on for 30-degree weather, and people passed me by like I was nothing.
My family rarely checked on me, and if they did, it was as if nothing was wrong, as if I wasn’t on the streets, surviving. This could have been the result of my downplaying my situation and talking about life as if I was living it up and successful. I, too, came to believe the lie I told myself, as if it were normal. I lived place to place, slept outside, scraped up food here and there, and tried to be Mr. Socialite of the streets.
When your loved one is living outside, you learn to read the weather differently. Rain isn’t just rain; it’s a threat. Winter isn’t just cold, it’s dangerous. A missed call isn’t just silence — it’s fear.
You carry questions you can’t answer:
Are they safe? Are they warm? Are they using? Are they eating? Do they know they’re still loved? And perhaps the hardest question of all: How do I help someone who isn’t ready, or able, to come in?
People don’t choose to be outside because it’s comfortable. They choose it because it’s the last place where they feel in control. For some, it’s untreated trauma. For others, addiction. For many, it’s mental health struggles, generational poverty, or a lifetime of being told they’re not enough.
Believe it or not, those who are outside are there by choice, specifically in Owensboro. We have a town that is full of resources, even with the housing supply gap. Some may say shelters are full, and that is true, but if a person is honest with themselves and ready to address the core issue, then they can find a bed at a treatment center for substance use or an inpatient bed for mental health issues.
When I was living to and fro, I was unwilling to be honest with myself to get the appropriate help. Yes, there were shelters, but I was in denial about being homeless to begin with. Secondly, what I really needed was treatment, transitional housing, and a job. These things wouldn’t be identified until later. When the pain of remaining the same outweighed the pain it took to change, then I started getting honest with myself.
My time homeless was long-lived, mostly due to my lack of honesty with myself. But it was also easy to stay in denial because I still had support. I still could get clothing, smoke, food, and make others feel responsible for taking care of me, so why do anything different? Once I changed my life, I could look back and see that I would’ve been ready to change long before I did, had things not been so easy.
My parents would send me money, bring me food, clothing, or whatever it was I told them I needed. It was never bad enough to do anything different.
Later in life, after overcoming my issues, my parents stepped back and identified where they could’ve been a little tougher with their love. Where they enabled me, they didn’t want to feel guilty for my situation. They didn’t want to worry or lie awake at night regretting telling me no. Instead of telling me the truth and pointing me toward the resources I needed, they felt an overwhelming desire to just do it for me — and that stole my self-determination.
Looking back today, we can see how tough love, truth, and giving a person direction to help themselves builds self-determination, which builds self-motivation, which builds self-esteem, which builds progress, which builds achievement, which inevitably leads to taking ownership of one’s life.
My parents have apologized over the years for not getting their feelings out of the way and doing what was best for me instead of what felt best for them. I, too, can see how, in my line of work, helping others sometimes feels wrong, but I know it’s the right thing for them or for the masses. Only my experience and education have taught me these things.
Outside, a tent, a camp, or a car becomes a place where no one judges you. No one demands anything. No one expects you to be someone you can’t be right now.
I want to be clear about something important: none of this is meant to criticize or diminish the work of outreach teams. Outreach is essential. Outreach workers, church groups, and volunteers are often the only consistent human contact someone living outside has. They bring food, clothing, blankets, and, most importantly, connection. They meet people where they are, without judgment, and they build the trust that becomes the first step toward change.
When I was outside, outreach workers were sometimes the only people who looked me in the eye. They reminded me I was still human. They reminded me I mattered. Without that, I might not have survived long enough to get honest with myself.
But outreach has a specific purpose. It stabilizes. It reduces harm. It keeps people alive. What it cannot do, what it was never designed to do, is replace the deeper work of treatment, shelter, structure, accountability, and long-term support. Outreach opens the door. Empowerment helps a person walk through it. Healthy helping means understanding that both roles matter. Outreach meets immediate needs. Shelters and programs meet long-term needs. And families, friends, and communities help bridge the gap between the two.
Helping others is so much more than a simple act. It’s more than what feels good in the moment. True help doesn’t always feel good. True help takes stepping back and asking yourself:
- Is what I’m about to do best for them or best for me?
- Is this what they truly need?
- Will this create further harm or trauma?
- Does this promote self-esteem, dignity, and self-determination?
- Does this move them toward thriving, not just surviving?
Healthy help empowers. Unhealthy help enables.
Shelters like St. Benedict’s and the Daniel Pitino Shelter need you, need the community, and need those who need our facilities. Even shelters and their employees are constantly evaluating services, delivery, policies, culture, and climate. We adjust, adapt, and evolve so we can be effective for those inside and those who have yet to come inside.
But we cannot do it alone!
Written by
Harry E. Pedigo, MSSW, CENM
Executive Director
St. Benedict and Daniel Pitino Shelters
