I've negotiated leases worth more than I'll admit in writing. I can read a rent roll like a bedtime story. And none of it prepared me for the quiet panic of being asked to help with something that actually affects lives in the most fundamental way: giving them a home.
Let me back up.
I knew Kim Haywood from her Dead Center Film Festival days before she worked with the Homeless Alliance, and Meghan Mueller and I were both in Leadership Oklahoma City LOYAL XVII (the best class ever). Before the titles, before I had a committee seat, before “the Homeless Alliance” was a line in my bio — they were just people I respected, doing work I admired from a comfortable distance. So when the ask came, I said yes the way you say yes to friends: instantly, a little flattered, and gloriously underinformed about what I'd signed up for.
For a little over a year I've served on the Facilities Committee, and that's when the comfortable distance of “someone else is handling it” disappeared.
If you've never toured the campus, here's what a tour actually is: it's sensory, and it stays with you. The day shelter. The winter shelter. Buildings built to code that are being used at 10x their designed volume. A shower that is getting dozens of uses each day and thousands of uses a year. A kitchen turning whatever was donated that morning into three meals for more than 300 people — Chopped, times 900, every single day, no dramatic music, no commercial break. You see it. You hear it. You even smell it, all at once. And it does not leave you when you get back in your car.
The thing I can't stop thinking about is the case managers. They are at ease in the hardest rooms I have ever stood in. Not numb — at ease. Calm, steady, unflinching, as if they knew this was their life's work. They are the single greatest testament I know to resilient people doing the hardest possible job, and they do it daily, mostly unwatched.
Somewhere on that campus the flattery wore off and something heavier took its place. These are my friends. This work matters more than I think I have the capacity to help with. And that's a strange, uncomfortable feeling for a guy who's used to being the one who solves the problem in the room. The fear isn't will I show up. The fear is what if I care about this more than I can help?
Here's the reframe that got me unstuck.
By the grace of God, there go I. A friend of mine, Christopher Stinchcomb, used to say that every time he passed someone experiencing homelessness he'd think: who didn't love you enough to stop and help? Who didn't love you enough to be there in the moment of need? He's right, and it's a gut-punch, because most of us have had a stretch where the bad luck compounded — one thing, then another, then another — and the only reason we didn't end up somewhere much worse is that someone stood in our corner. The distance between a hard season and the street is often exactly one person who refuses to look away.
I can't be that person for a stranger. I'm not trained for it; the case managers are. But I can do one thing I'm completely certain of: I can make a spectacle of myself, and convert every bit of attention it earns into dollars for the people who are trained for it. Attention is the one currency I know I can mint. So I'll mint a lot of it, and hand the whole pile to them.
Which is how a perfectly sane 39-year-old commercial real estate broker ends up running for homecoming royalty in a traffic-cone-orange tuxedo, cane and all. (That photo is AI-generated — I'm not above using the technology to pre-visualize my own humiliation. The real outfit arrives August 15th. And the wardrobe, let's say, has contingencies if the numbers demand them.)
If we're handing out crowns, though, I want to be clear about who actually earned them: Meghan Mueller, who started here as an intern in 2013 and now runs the entire organization. Haley Phelps, who keeps the whole operation standing. Kim Haywood, who I knew as the heart-forward friend that was there for the shenanigans and the tears (love you, Kim). Carrie Sauer, who met with me and gave me my first dose of reality — she's tough as nails and has one of the most heartwarming smiles. And every case manager who makes “at ease in the hardest room” look like a choice instead of a miracle.
I'm just the guy willing to look ridiculous so you'll look their way.
The crown is the bit. The fear of not being enough is real. The work is the point. Help me not let them down — grab a ticket with code HeresTheDiehl for Starry Night on August 15 at the Will Rogers Theatre, or vote with a donation in my name. Every dollar is matched up to $200,000 right now, so yours counts twice.
