Episode Transcript
[00:00:01] The story I'm getting ready to tell you was not on my 2026 plan.
[00:00:05] Not even close. Welcome back to the Confessions in the Home Office. My name is Wendy Hill.
[00:00:11] This week, I'm not talking about business. I'm not talking about marketing.
[00:00:16] And, you know, I have a list of topics that I'm going to cover. And then there's things that just show up in your life, and they keep kind of tapping you on the shoulder. Or I'll say that God throws a brick at my head, and I realize that maybe that's the story I need to tell.
[00:00:32] So here we go.
[00:00:35] Be patient with me.
[00:00:37] A few months ago, this was back mid January, I believe it was January 18th, to be exact.
[00:00:43] My husband and I were out working at Starbucks on a Sunday afternoon. He's a history professor. Of course, I'm running my marketing company.
[00:00:51] We don't work on Saturdays, but we prep hard on Sundays. Sometimes it's home in our offices here.
[00:00:58] And a lot of times we like to get out on Sunday, go to a coffee shop, go someplace where we can have lunch and do some work, get some things done.
[00:01:06] When we wrapped up, we decided we were going to go get gas at Costco. You know, like those adult things that you have to do. And we were going to turn out of the parking lot one way, and we saw the traffic was backed up. And if you know anything about Greenville, South Carolina, everybody has moved here. Traffic is insane. And it has never been that way until just the past past few years. So we decided to cut through a parking lot and head to Costco, another way to try to beat some of the traffic.
[00:01:35] And so we cut through a parking lot that had.
[00:01:38] That used to have a Burlington Coat Factory store that, you know, the sign had been taken down, maybe three or four cars in the parking lot.
[00:01:48] Not much going on. And we saw a guy with two dogs up on the sidewalk.
[00:01:54] And my husband immediately said, there's two dogs over there on the sidewalk. And I thought, oh, gosh, please don't go pick them up, because he has the same mental illness I do. We would rescue every animal we could.
[00:02:07] And I said, there's a person with him. Let's go get gas.
[00:02:12] So we went to Costco, and on the way back, Reggie said, let's go see if that guy and his dogs are still there on the sidewalk.
[00:02:20] And there they were.
[00:02:22] So Reggie stopped and asked, rolled down the window, and he said, are you hungry? Do you need anything? And that was it.
[00:02:28] The young man said he was mostly worried about his dogs and Asked if we could get them water and some rawhide.
[00:02:35] And that detail stayed with me because he didn't ask for money.
[00:02:40] He didn't give us some big speech.
[00:02:43] He was worried about his dogs. We left, we went over to McDonald's, and we went over to Dollar Tree, grabbed some things, came back, and next thing you know, Reggie's out of the car.
[00:02:58] And I was uneasy, and I don't say that to be unkind. I think most people would understand that feeling. You see someone you don't know in an unpredictable situation, and your mind starts filling in the blanks.
[00:03:12] I know I've watched too much Dateline. I know I listen to too many true crime podcasts, but Reggie's just talking to him like he had known him for a while.
[00:03:22] And that's Reggie. He's quiet, he's stoic.
[00:03:26] He's not extroverted at all.
[00:03:28] And when he stands up and walks up to you, he's pretty intimidating.
[00:03:32] He says he's six. Six. I think he's taller than that.
[00:03:36] But he had a confidence about him, and he was going to talk. He was going to talk to the young man and make sure they're okay and try to figure out what's going on.
[00:03:46] At the time, I don't think either of us understood that one small exchange was going to grow into months of involvement. So over the next couple of days, Reggie had asked him for his phone number.
[00:03:56] He checked in with him. He would text him. He called him. We dropped off some more supplies. We found out his name was Tyler.
[00:04:04] We started to learn just a little bit at a time.
[00:04:07] He'd been homeless for a while.
[00:04:09] He stayed at a campsite that he had found away from other homeless people because he had his two dogs with him. He was responsive. When Reggie would text him, he was appreciative. He was not pushy.
[00:04:23] He did not act entitled. He did not come to us with a giant list of requests. It was just little things at first, but the weather became a serious issue.
[00:04:31] See, in Greenville, we had ice storm, and then we had snow shortly after that. So there were, like, two waves of panic in the town. We're not equipped to have our road scraped. Power goes down, everybody panics at the grocery store.
[00:04:49] And the ice storm was coming. And suddenly this didn't really feel like a situation where somebody just needed some dog food and some encouragement.
[00:04:57] It started to feel dangerous. It felt urgent.
[00:05:00] I started thinking, okay, he can't be outside in this. Not with the temperatures dropping, not with the dogs, not with the way things were Headed.
[00:05:10] So I did what I needed to do.
[00:05:12] I got on Facebook. And first I went to my neighborhood Facebook page and said, here's what's going on. Does anybody have any supplies?
[00:05:21] And that really pulled me out of my comfort zone.
[00:05:26] We don't ask for help around here.
[00:05:28] I'm just the person who helps. I'm the one who figures it out. Reggie is great at figuring things out, but we knew this was more than what we could do.
[00:05:39] And our neighborhood is huge. It's one of the largest ones in South Carolina. And they started to show up.
[00:05:46] I put out my Venmo. Some money started rolling in.
[00:05:50] Little propane cylinders rolled in heaters, hot hands, dog food money. Practical things that could make an immediate difference.
[00:06:01] It made me realize that, you know, the Internet's just not always a dumpster fire. You know, our neighborhood Facebook page is a dumpster fire a lot of times.
[00:06:10] But people were really showing up. So at the last minute, this was, I believe, around January 30th, Tyler let Reggie know he had enough donated money from some people that he had talk to for a motel night. So it was okay. We've given him supplies for him to stay outside in the cold.
[00:06:29] We had a couple things left.
[00:06:31] We were like, he's not gonna have to be outside.
[00:06:34] He's gonna be able to stay in a motel. He had found a place that would let the dog stay with him. I can't even explain the relief. I was in tears.
[00:06:43] Reggie was in tears. I just knew those dogs were gonna freeze to death. I knew that something could happen and his supplies could be stolen, he could be hurt, and nobody would be out looking for him.
[00:06:54] So we met him at the motel.
[00:06:57] We had a little bit of money from the neighborhood.
[00:07:00] We put in our money to cover more nights to try to get him through the bad weather.
[00:07:05] And then what started us concerned about getting him through one stretch of brutal weather turned into now you're there for a couple of weeks.
[00:07:13] I still remember thinking, I can't believe all this is happening. I can't believe these supplies are showing up and this money is showing up.
[00:07:20] And all these people just chipped in what they could, and they decided that he mattered enough.
[00:07:28] So safety for a few nights was only one piece of the puzzle. With Tyler.
[00:07:34] The biggest barrier he was facing was his identification, his out of state id. Not a driver's license, just an ID had been stolen when he was assaulted down in Columbia back in late 2025.
[00:07:48] His wallet was taken, and without his. His ID, so many doors stay closed, you can't just decide to go put your life back together in the paperwork that proves who you are.
[00:08:00] When it's gone, you can't do. You can't go get a job.
[00:08:04] You really can't do anything about getting put on SNAP Public assistance housing. Listening. You can't do anything.
[00:08:13] So if you've ever had to try to replace a driver's license or Social Security card or any official document, life just kind of grinds to a halt when one piece is missing.
[00:08:24] Now imagine trying to do that while you're homeless, dealing with trauma, going to Burlington Coat Factory to charge your phone and your laptop every day until he got into the motel and trying to keep two dogs safe and probably not really trusting people.
[00:08:40] So that was the beginning of learning something I think a lot of us don't understand unless we're close enough to see it.
[00:08:45] Progress is slow.
[00:08:48] It is not. One breakthrough and then suddenly everything is fixed. It's little things, tiny things, really slow things.
[00:08:57] One phone call, they're not in, they're on vacation, they'll be back.
[00:09:03] One form, one ride somewhere, one envelope in the mail, one appointment, one follow up.
[00:09:11] Somebody finally calls back.
[00:09:14] It's a thousand little pieces that we have to line up.
[00:09:17] And it's exhausting to think about somebody who's been homeless for a while having to coordinate all that.
[00:09:23] But as the weeks went on, people kept helping. I kept posting on Facebook, Tyler update with the date.
[00:09:30] Clothes were donated, food was donated. My mom doesn't need much of a reason to shop. She went out to get hoodies for him because he needed layers.
[00:09:39] Reggie ordered jeans for him online. People made home cooked meals that he could just heat up in his motel room.
[00:09:45] Someone told us about Hack Greenville where he could learn more about programming and talk to people on Slack channels.
[00:09:52] He's interested in computers, interested in programming, also interested in automotive.
[00:09:58] We started hearing bits and pieces of what he wanted for himself and it made all this feel even more important. He was not just trying to survive, he was trying to start putting a future together.
[00:10:09] This is a smart guy and he's funny.
[00:10:13] He reminds me a lot of my son with the south park and the family guy humor and how he can weave that into any conversation. But he's thoughtful. He doesn't have a mean bone in his body.
[00:10:25] He's not just a person in need, he's a whole person.
[00:10:28] He has interests, skills, preferences. He has goals.
[00:10:32] He wants to learn new skills, those details, because those details, they really matter because it pushes back against the lazy way people or the way that people think that homeless people are lazy. I guess that's the way to say it.
[00:10:52] People want things to be simple. They like categories.
[00:10:55] They like to think someone's either trying or they're not trying. They're deserving or under deserving. They're motivated or they're lazy.
[00:11:02] But real life is not like that at all. People are so complicated, and trauma is really complicated, and systems and government and rules are really complicated, and progress is complicated. And once you sit across from someone and hear them talk and laugh and explain what they're good at and what they hope for, it gets harder to reduce them down to just one label.
[00:11:29] So a few weeks later, Reggie and I took Tyler to Olive Garden for lunch.
[00:11:34] That meal is something that I don't think I will ever forget.
[00:11:38] He ordered a full meal. It was a late lunch, and he struggled to eat a full portion because he was not used to having that much food in front of him. So as a mom, that hit me hard.
[00:11:49] When he got up and excused himself to go to the bathroom, just to walk around so the food could go down so he could finish the meal.
[00:11:56] I thought I was going to lose it at the table.
[00:12:00] It was just a simple reminder of what instability does to a person. It changes what feels normal. It changes what your body expects. It changes how you move through the world.
[00:12:11] And sitting there with them and watched him relax more as the meal went on. And I apologized to him when we got started. I said, I've talked to you here and there. Reggie's been doing so much of this work, has been insane this year, and which is wonderful, but I have worked like crazy.
[00:12:29] I have so many questions for you. But I ask questions for a living. And when it's too much, tell me to stop. You're not going to hurt my feelings. I just want to know so I can help you.
[00:12:40] He said, okay, you got it.
[00:12:43] So we would eat a bite or two. I'd ask him another question.
[00:12:47] And as the meal went on, he relaxed. He looked me in the eye more, and I could start hearing him laugh about things, make some jokes. He would laugh when we would talk about how we were older.
[00:12:58] And I remember thinking trust is built on moments like this. Not solving his big problems and just showing up and being his friend and being there for him.
[00:13:11] So we learned more over time. Tyler's been all over the United States over the last 11 years.
[00:13:17] He's on his mom's cell phone plan. I am so thankful for that because he can stay connected with her. He can stay connected with Us and he can make phone calls to make his situation progress.
[00:13:29] We don't know everything or anything really about family dynamics.
[00:13:33] What we do know is he doesn't want to go back home. He's been assaulted more than once over the last few years while he's been on the road.
[00:13:39] He's dealing with PTSD and anxiety. He gets overwhelmed.
[00:13:44] One of the times he was assaulted, he told us they would have likely killed his dogs if the dogs had been there with him. He was just fortunate enough somebody was watching the dogs when he was walking, where he was walking that day when he said. That explained so much about the way he moves to the world, the way he protects them, the way he has held onto them, and maybe why accepting help has not always been easy for him. He tells me all the time, I don't know how to ask for help.
[00:14:11] And I said, well, just ask for one thing.
[00:14:13] You don't have to give me the whole list. Let's just tackle what the most urgent thing is right then.
[00:14:20] Helping someone is not neat. I have learned it is not one long string of heartwarming moments. There are times when we were all encouraged and hopeful, and I went to bed that night and prayed, oh, everything was a good day. That was. That was so great. He's gotten all this stuff done.
[00:14:38] And then there's times that we felt stuck. And there are times that I've been really frustrated.
[00:14:43] He's missed meetings that he was supposed to go with me to get help because he was anxious, and he ended up oversleeping. And there was moments I thought, come on, we're trying so hard to keep this moving. Why are you letting me down? And then I realized, this isn't about me.
[00:15:01] There were times when anxiety got the gotten away from him more than once. There were times when, you know, we're waiting on one more piece of paperwork, and it just felt so ridiculous. And I think it's important to say that because a lot of times when people talk about helping, they either make it sound like it's all beautiful and inspiring, or it's just hopeless and draining. And it is neither of these things all the time. It is both.
[00:15:24] It is deeply meaningful and at times, incredibly frustrating.
[00:15:29] So one of the hardest lessons has been realizing we can't do the work for him. We can open doors. We can make introductions. We can try to get lists.
[00:15:39] We can pay for a motel room to keep him safe.
[00:15:42] A lady at our church has been keeping him supplied in so many groceries. And I will be forever, forever grateful for her.
[00:15:50] We can get him a bus pass.
[00:15:52] Those are all helpful things and we can point them towards resources. But there's only parts that he can do and there's only forms that he can fill out and sign and there's only meetings that he can attend.
[00:16:04] I can be his emergency contact. The other day he goes, I don't even know your last name. I need to write. I need to write it down on a form.
[00:16:12] There are conversations only you can have with caseworkers and agencies because of privacy. He has to do the rest.
[00:16:18] He needs ownership in his own life.
[00:16:21] He needs momentum that belongs to him.
[00:16:25] So there's been a balance in all this. Wanting to help and knowing when to step back, that he's the one that's moving his own life forward.
[00:16:33] And there's also the dogs that became the story from day one. He calls them the ladies. So of course that's what we call them.
[00:16:40] Nala had a growth on her leg and it was starting to rupture and we got donations. Our vet gave us a discount and operated on her leg. And she's doing great.
[00:16:56] So she recovered in the motel room, what I call, you know, the cone of shame.
[00:17:01] And she's sweet and the other dog is sweet. And they are well behaved and a lot better behaved than many humans that I know.
[00:17:11] These dogs are just not an extra detail. They're emotional anchors for him and their companions, their protection and their consistency. And they're his family.
[00:17:22] And I know there's always going to be people who hear a story like this and think, well, if he would just give up the dogs, housing would be easier.
[00:17:31] Maybe that's true on paper, but real life is not lived on paper.
[00:17:36] Real life is lived in relationships and attachment and grief and fear and loyalty.
[00:17:42] Sometimes the thing that makes a situation more complicated is also the thing helping someone survive it emotionally.
[00:17:50] So then finally, after all the waiting and all the mailing issues and all the checking and calling and hoping, his ID arrived from the other state. A replacement id. I still laugh thinking about the level of drama around that mailbox when I saw it on my United States Postal Service email I get at 7:30 every morning. And my husband gets it too. I cried, and I think he cried on his way to teach.
[00:18:16] We were acting like the lottery had been won. In a way, it had, because the card represented movement.
[00:18:23] It was a giant, giant barrier. Finally coming down, Reggie took him to the dmv. He swapped out that ID for a temporary South Carolina id. Then his permanent ID came.
[00:18:34] Then he was able to work on a Social Security card.
[00:18:37] Suddenly, after weeks of feeling like we were pushing against a locked door, things started moving forward.
[00:18:45] Now he could focus on work, benefits, housing, longer term planning. He started applying for jobs. He had interviews.
[00:18:53] He connected with Tryon Mercy center here in Greenville, which is a fantastic organization. They, it's kind of like a one stop hub on Wednesdays, all kinds of services.
[00:19:04] And he started working through the services there. He has a bank account set up.
[00:19:09] He's getting closer to snap benefits.
[00:19:12] Every one of those things sounds small when you say them quickly, but together they start putting a structure together for him and they create dignity. It's not just about survival anymore, it's about building a life.
[00:19:26] So none of this has a magical ending, but now he has more of a schedule.
[00:19:35] Things are leading somewhere and so on. So housing is still the biggest challenge. It has not magically been resolved. The motel has been a bridge.
[00:19:45] Hopefully we'll keep getting more donations to keep him in. The longer he's on a housing waiting list, it could take another six or eight weeks before he gets a place.
[00:19:57] So we've driven a, you know, looked at lists, crossed off places, talked about what's realistic and what's not.
[00:20:06] It's hard and it's uncertain and it's brutal when someone's already carrying anxiety and trying really hard not to slide backward.
[00:20:18] The part that's probably that weighs on me the most is he's been on the streets for 11 years and I know that was my choice.
[00:20:25] It's a long time to live in survival mode. It's a really long time.
[00:20:30] You don't just hand someone an id, a job, a bank account, and expect for them to immediately settle down.
[00:20:37] You don't just hand them a motel room and assume they know how to move through all this without fear.
[00:20:42] He's trying to stay away from a lot of people in the homeless community because he said the people that he has met in the homeless community have a lot of addictions. He's sober, he wants to stay that way.
[00:20:56] The downsides, isolation. Isolation is dangerous in its own way. He's talked to us about this.
[00:21:02] When you're not around people, you're anxious, your thoughts have too much to run wild. I call that the head trash that just builds. We all get it.
[00:21:12] So there's a practical side of helping and then there's the emotional, mental side and everything matters.
[00:21:20] One of the things I've thought about through all this is how easy it is to talk in broad terms about homelessness until you're standing in the middle of one person's really specific reality.
[00:21:32] Broad terms are comfortable. They let us stay detached. They let us have opinions without involvement.
[00:21:38] But one real person changes things. One real person with a name and a sense of humor and kindness and two dogs and a list of obstacles and a story you only partly know changes the way you think.
[00:21:54] I've also thought about how this wasn't on my list for 2026.
[00:21:58] This was the year I was really going to bust it with work I do every year, but I always think I can do more.
[00:22:04] This was the year I was going to map out the master plan for the farm.
[00:22:09] I did not have this written down. And I know that life throws curve balls.
[00:22:18] So it was just a random change in route to avoid Greenville traffic.
[00:22:24] It was a moment that could have gone another way if we just kept driving or if we didn't loop around and come back.
[00:22:31] And that's what gets me, because I think of so much of life is like that.
[00:22:37] We think the meaningful things are going to arrive with these big announcements and big bows and clear categories and neat plans.
[00:22:45] A lot of time they do, but a lot of times they don't.
[00:22:50] A lot of times they arrive looking inconvenient and messy and emotionally complicated.
[00:22:56] They arrive when you're in a rush. We were in a rush that day.
[00:23:01] We were hurrying to get home. We had worked too long.
[00:23:05] They arrive when you're headed somewhere else. They arrive disguised as something you didn't ask for.
[00:23:12] But I will say one of the most amazing things has been watching other people step in. Neighbors, friends, strangers, former clients.
[00:23:22] One lady I went to one meeting with when I was doing contract work with an agency 16 years ago. I spent an hour and a half with her.
[00:23:31] She venmoed me a ton of money.
[00:23:35] People bringing meals, people dropping off clothes, people texting me for his sizes.
[00:23:41] Stuff just shows up.
[00:23:43] People keep checking in.
[00:23:46] I went to a Queen of Hearts Valentine's luncheon. One of my friends said, tell everybody about Tyler.
[00:23:53] I go to another event a few weeks later, and everybody says some of the same people are there. Tell us about Tyler. What's going on?
[00:24:02] So what I've realized that people are often more generous than we give them credit for. I think sometimes they just need a real story and.
[00:24:10] And a way to help.
[00:24:11] And they need to know that their effort matters.
[00:24:14] And they need to see the human being in front of the need.
[00:24:20] This doesn't mean that all this has been met with kindness. I'd be lying if I said that I posted questions on a public group on Facebook anonymously looking for resources, and got torn up by keyboard warriors. I was mad. I was screenshotting those people's profile pictures and their names and thought, what am I going to do with that?
[00:24:41] That part was discouraging, but it also reminded me that there always be people watching from the sidelines with opinions, and there's always going to be people who think they know exactly what should be done when they have no skin in it.
[00:24:56] I'd rather spend my energy on Tyler and on the people who show up and make things better.
[00:25:03] So at this point, we're mid April when this is being recorded.
[00:25:08] Tyler's been off the street since the end of January. That is huge. And that is because our friends and clients and church members and neighbors and friends of friends, he's made progress.
[00:25:23] He has an id, he's working. He has a bank account, he's moving towards benefits.
[00:25:30] He has food. He's had help with transportation.
[00:25:34] He's had dog surgery for his dog, and she has healed.
[00:25:41] That doesn't mean everything's fixed. It means movement, momentum. It's real.
[00:25:46] And when someone has spent 11 years surviving, momentum matters.
[00:25:54] So I think one thing that has really stayed with me is that helping is really less about rescuing and more about staying around, staying present, staying realistic, staying available, and just being willing, especially when progress is slower than you want it to be.
[00:26:12] And being honest about getting frustrated without giving up on someone.
[00:26:19] He didn't become stable overnight, so staying committed long enough is going to be important.
[00:26:29] I don't know how the story ends. I wish I did.
[00:26:32] I wish I could snap my fingers and say, everything's going great before we go on vacation this summer. I don't know if that's going to happen.
[00:26:38] I wish it would.
[00:26:41] I wish I could tell you that. That Tyler's in a great apartment and has a promotion and is working on new goals. We're not there yet, but real life is that he's trying. And some days trying probably cost him more than other people realize.
[00:26:59] Real life is that we're still helping, still hoping, still making calls, still taking his calls, and still watching for the next open door.
[00:27:08] I'm glad we stopped.
[00:27:10] I'm glad Reggie got out of the car.
[00:27:13] I was nervous, and I was thinking, what the hell are you doing?
[00:27:17] I'm glad we didn't look away, and I'm glad our friends and our neighbors showed up.
[00:27:23] And I'm glad that Tyler is letting people help him.
[00:27:26] I told him the other day that I thought we were like 85 or 90 people. Who had contributed to money and resources, and he was blown away. And it gave him another.
[00:27:37] I don't know, it gave him another burst of energy to keep going with things. He said, I had no idea that many people knew about me.
[00:27:44] And I said, oh, yeah, we tell everybody who will listen.
[00:27:50] So what I've learned and just kind of recapping to finish this up is not every problem can be solved right away.
[00:27:59] And sometimes problems don't get solved at all.
[00:28:02] And we're not experts. We didn't know anything about any of this, and we still don't.
[00:28:08] We've asked a lot of questions. We've learned a lot of things.
[00:28:12] We realized that some of the solutions that we had weren't realistic.
[00:28:16] So this whole experience has made me think differently about people that I pass every day. And I know there's scammers out there. I know there's people who are dishonest and people who aren't homeless.
[00:28:30] But it's made me think differently about how fragile life can be and how many layers sit underneath the word homeless.
[00:28:40] It's made me appreciate how much paperwork and transportation and mental health and timing and trust, how they all need to intersect.
[00:28:48] And it's made me more aware that real change usually takes longer than we want it to.
[00:28:53] That doesn't mean it's not happening.
[00:28:56] So that's my story about Tyler.
[00:28:59] It's not a business lesson, but it's a neat takeaway.
[00:29:04] And it's just a really real reminder that life has a way of handing you something unexpected and asking, what are you going to do with this?
[00:29:14] We just keep taking the next step, and we just keep putting our brains together and try to figure it out.
[00:29:21] And I think that's enough for now.
[00:29:25] Tyler's closer than he was.
[00:29:29] So that's my episode for this week.
[00:29:33] Next week, I'll probably be back, or two weeks. When I'm back, another episode about marketing and business. And maybe not be as emotional on the podcast, but I'll have more details in the show notes if you want some more information.
[00:29:50] And that's it for this week. I'll see you soon.
