Look Again

August 15, 2026

Dear Reader,

Greetings from Parkwood Studios in Almost Heaven West Virginia, somewhere between "soggy, summer swamp" and "first colorful signs of fall."

For those who are shipping kids off to college this week, I send you a knowing, empathetic nod. As I remind myself each year at this time: "It's okay to feel that mix of emotions."

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Look Again

Wisdom Lesson 78

It was about 5:15 PM on a Thursday in early July, and the temperature was 99 degrees.

A heat dome had settled over much of the eastern United States that week. Charleston had spent days flirting with triple digits. The late-afternoon sun beat down on Washington Street like a heat lamp, radiating off the pavement.

My wife, Lisa, and I were on our way out of town. I'd just picked her up from work, and we were headed toward the interstate, hoping to get an early start on the drive to the family lake cottage in Michigan.

Then we hit a red light.

Standing just to the left of my SUV was a man holding a cardboard sign.

He wore blue jeans but no shirt. Tattoos covered parts of his arms and torso. Sweat glistened across his face, neck and chest. He was unshaven and looked like he'd had a rough go of things.

I don't remember what his sign said.

Maybe that's because I've been trying to stop reading the signs.

Closing the Courtroom

For much of my life, encountering someone asking for money along the road could open a little courtroom in my head.

Is this person really homeless?

What's he going to do with the money?

Am I actually helping?

Lately, I've been trying to close that courtroom.

Admittedly, I'm a work in progress. Someone still trying to strip away old layers of judgment, privilege and pride. As part of my faith journey, I've also been trying to take more seriously Jesus' command to love my neighbor as myself. And not to overthink it.

So I've started keeping a small stash of food, money and clothing in my vehicle.

Let's be clear. I'm not claiming to have solved homelessness. But I am trying to get better at seeing the person in front of me and responding with love before judgment.

This afternoon was different, though, because Lisa was with me. Most of these encounters happen during my daily work commute. So she'd heard my stories about them, but she'd never witnessed one firsthand.

I lowered my window, stuck out my arm and waved the man over. He shuffled over to my side of the Kia.

I offered a handshake. "Hi. My name is Skip. What's yours?"

He took my hand and replied, "My name is Robert."

I told Robert I had something for him and handed him a granola bar wrapped with two one-dollar bills, all held together with a rubber band.

Robert looked me in the eye and thanked me.

The light turned green.

He stepped out of the traffic lane and back onto the shoulder near the bridge.

I checked my rearview mirror. No cars. Then, I looked over at Lisa. She looked right back at me. We didn't say anything. But we felt strong emotions. Good feelings, mostly.

Then, as I turned toward the windshield and the road ahead, I saw Robert walking back toward my window.

What Does He Want Now?

I wish I could tell you my first reaction was generous.

It wasn't.

Oh no. What does he want now? More money?

There was another thought underneath that one.

Are we safe?

I'd just shaken Robert's hand. Learned his name. Looked him in the eye. I'd just shared a moment with my wife about seeing him as a fellow human being.

Yet within seconds, I was judging him again.

I lowered the window. Robert crouched toward us. Both of us glanced at the traffic light and then behind my SUV. A car could arrive at any moment.

"Skip, you all look like nice, generous, praying-type people."

Then he told me what he wanted. "I'd ask you to pray for me," he said. "But I really need you to pray for my son, Dawson."

Dawson lived in New York City. He'd moved there for a job that paid well, Robert explained, but the work was dangerous. Very dangerous, apparently. Robert worried about him every day.

"Would you pray for Dawson?" he asked. "Would you pray for God to protect him?"

I told him we would. Then I asked him a question that came from my heart as a father to a son.

"Will you get to see him anytime soon?"

Robert stood upright, glanced skyward and scratched his head for a moment.

"Hopefully," he said. "Maybe in November, around Thanksgiving."

I nodded and promised again that we would pray for Dawson. The light was still green. It was time for us to go.

Dawson's Dad

"That was a real human being right there," I said to Lisa as we drove away. "A real person. Flesh and blood. A father with a son. Fears and worries of his own."

Nothing about Robert had changed during that second conversation. He was the same man standing beside Washington Street in 99-degree heat.

Robert hadn't changed. Our view of Robert had.

Before he returned to our window, I could have used all sorts of labels to describe him: poor, homeless, smelly, beggar, rough ... down on his luck. Some might even have been accurate. But none of them was Robert's identity.

We'd learned something else about the man standing beside Washington Street: he is Dawson's dad.

Somewhere hundreds of miles away in New York City was a son, whose father worried about him every day.

I still wonder what Dawson does there. Does he work high above the city on a construction site? Is he around cranes and heavy equipment along the waterfront? Does he work in law enforcement or security?

I'll probably never know.

I also don't know why Robert was standing beside Washington Street that afternoon. And I don't know whether Robert will get his wish of seeing Dawson around Thanksgiving.

I sure hope he does.

There is so much about both men I'll never know. But Robert told me enough to understand something I'd missed.

More Than Our Labels

We all carry labels. Some we choose. Others are assigned to us. Some are accurate; some aren't.

Parent. Leader. Successful.

Retired. Widow. Senior.

Addict. Unemployed. Homeless.

A label can describe something real about us. A circumstance. A struggle. Perhaps, a season of life. But a label is not an identity.

Robert was more than the labels we'd assigned to him.

I couldn't see it on his cardboard sign. No, I learned it when he came back to the window and told me about someone he loved.

As we drove toward the interstate, Lisa pulled out her iPhone and opened Apple Notes. She created a note so she could remember the prayer request we'd promised to honor.

The title she typed was:

Homeless

Underneath it:

Robert and son Dawson

That's the entire note.

Four People

I've thought about those few minutes on Washington Street many times since. There were four people in that story. Two were sitting inside an air-conditioned SUV. One was standing beside the road, sweating, in 99-degree heat. And one was hundreds of miles away in New York City, with no idea that three people in West Virginia were talking about him. Four people with different circumstances and different lives.

We gave Robert a granola bar and two dollars that afternoon. Robert gave us something, too. He gave us Dawson's name. And with it, a glimpse of the person beyond the label.

That's what I'm still working on. Looking past the shorthand. Leaving room for what I don't know. Remembering that no matter how accurate a label may seem, there is always more to the person wearing it.

Lisa still has that note on her phone. We're still praying for Dawson. (And his dad.)

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Continue the Conversation

"Be the Kind of Leader People Remember"

A wisdom conversation with Bethany Meighen

When we step out of auto-pilot mode to help someone, to bless someone, it changes things. One person receives help. And often, the person doing the helping discovers something new, too—perhaps even something about themself.

As you'll hear in this warm, engaging wisdom conversation with Concord University President Bethany Meighen, such golden opportunities to bless others aren't limited to the people we encounter at intersections, curbs and shelters. Not by a long stretch. They're all around us, once we begin looking for them.

Discover what it means to live the life of a servant leader. You may begin to notice new opportunities to bless the people you encounter every day, whether at home, at work or somewhere in between.

I hope you'll pull up a chair and join us.

Listen to Episode 149 with Bethany Meighen

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Wisdom You Can Hold in Your Hand

Sometimes a few well-chosen words are all we need to see something differently.

Our Wisdom Card Set brings together 52 nuggets of timeless wisdom shared by guests of The Main Thing Podcast, beautifully captured on 27 premium cards.

Display one for a week, choose a message that speaks to your current season, or explore themes such as resilience, relationships, adaptability and faith.

It's a simple way to bring a little more wisdom into the places where you live, work and reflect.

Explore the Wisdom Card Set

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Word of the Week

Bedraggled (adjective)

Pronounced: | bə draɡəld |

Meaning: dirty and disheveled

Untidy, disheveled, or worn-looking, often from having been caught in bad weather or otherwise having had a rough go of things.

Origin: early 18th century English - “being thoroughly draggled." To make something wet and dirty, typically by trailing it through mud or water.

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One Last Thing ...

I'm leaving you with a challenge for this weekend, as you head into the coming week.

Be keenly aware of the labels you use as you move through your day.

Where and when are you assigning one? Pause and consider the following as you encounter each instance:

• Is this label necessary?
• Is it accurate?
• And what might I be missing about the person or situation behind it?

I'd love to hear about your experience with this challenge. Drop me an email and share what you learned. I may publish a few highlights in an upcoming newsletter.

​
​Looking forward-

~Skip

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Skip Lineberg

Host - The Main Thing Podcast

"Your 9-Minute Dose of Wisdom"

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