Here’s an experience I had that I’m sure many can relate to.

Mind if I sit here?” I asked, balancing a coffee and laptop in one hand, luggage in the other, scanning for an open spot in the lounge.

“Yeah, sure. Go ahead,” he nodded, eyes still half-locked on his screen.

We started with the usual small talk. Travel. The chaos of airports. The weather. Then work.

“I’m a Regional Sales Director,” he said, stretching slightly like the title had weight. “Northeast. I’ve got my own quota and manage a team of 15.”

I smiled. “So, you’re the guy putting out fires all week and then wondering why the house still smells like smoke on Friday?”

He laughed. “Exactly.”

But there was something else there. Not just the fatigue of a guy on his fourth flight of the week. Something deeper. Something personal.

When I asked about his family, his posture shifted. Less polished, more human.

That’s when he shared one of the saddest things I’ve ever heard.

“I’m tired of watching my kids grow up through pictures.”

“Keith,” he said, eyes lowering for the first time in our chat, “I’m tired of watching my kids grow up through pictures.”

That hit me.

“Four days a week on the road takes a toll on your health, peace of mind & happiness. Home Friday night. Missed birthdays. Missed school events, sports, recitals, missed moments watching my young children grow. Three great kids.

You know, the ‘how was your day’ stuff. Now, it all comes to me secondhand. Like I’m reading the Cliff Notes of my own life.”

He went on, describing how his wife’s family is in the Bay Area and how much she misses them. But they’re stuck in Atlanta. Because of his job.

How long have you been at your job?” I asked.
“Fifteen years.”

“So, if you had to decide today, risk-free, would you still choose to be there?”

Without hesitation, “No.”

I asked what he wanted, but instead, his excuses began to flow. Too old, too risky, too much responsibility, what jobs are out there that fit me, uprooting the family, needing financial security.

We pushed past the excuses and shifted from fear to faith.

Talking about what mattered. Family. Balance. Happiness. Health. More remote work. Living at home, not in an airport.

I listened. Then asked, “Okay, put all of that aside for a second. Pretend none of those reasons existed. What would be possible if you found a role with less travel?”

His shoulders dropped. His voice softened.

We pushed past the excuses and shifted from fear to faith.

“That would be a dream,” he said, almost like he forgot what it felt like to say something for himself.

We sat in silence for a moment, letting that land. Then he asked, “But who’s gonna hire a 50-year-old sales manager who hasn’t interviewed in over a decade?”

I raised an eyebrow. “Wait, you’re 50?”

He nodded.

“Damn. You’ve had a harder ride than me. I thought we were the same age.”

He smiled, but only halfway.

It wasn’t the years. It was the wear.

And I get it. I’ve met hundreds of people like Tom. Seasoned, good-hearted, great work ethic, smart, hard-working—but stuck. Not for lack of options. For lack of belief.

So, I told him the truth. “Look, man. Everyone around you will minimize your value. Your age, your résumé gap, your title. Don’t join the chorus. Be the one person in your life who stands up for you.”

That cracked something open.

For the next thirty minutes, we coached. I asked what his ideal role would be. What he really wanted. Not what was safe, but what was true. And every time he started a sentence with “Yeah, but…” I stopped him.

“This is the part where your excuses will sound like logic. But it’s still fear, dressed up as ‘being realistic.’”

Finally, I asked one thing: “Would you be open to applying to just one job?”

He nodded. “Yeah… I think I can do that.”

We exchanged info.

I offered to schedule a few calls, so I could support him around what he needed to make a dream life-change.

We cleaned up his résumé and social media profiles.week later, another email.

“Keith—I haven’t been on an interview in 15 years.”

So we coached that, too.

Then silence.

Two months later, I received a text:

“Keith, I got a new job at Amazon! A district VP; with no travel. And we’re moving to the Bay Area to be close to my wife’s family. You changed my life…”

Here’s the thing. I didn’t change his life. I didn’t do much.

I didn’t give him a job. I didn’t make a call or pull strings. I just listened. Asked the hard questions. Refused to let him shrink.

I asked him the questions he wasn’t asking himself because he was too stuck in the fear of change and the assumptions of the unknown, rather than the gifts received when working through fears and excuses, and what’s present on the other side.

That’s the thing about coaching and being a true leader. It’s not a job, or a checkbox on a manager’s scorecard.

It’s who you are and how you show up each day; being present enough to hear the fear, dreams and truth beneath the story that even a stranger is willing to share.

Sometimes, the most powerful impact you can have on someone doesn’t happen at work. They happen when you care enough to authentically listen and ask the right questions to someone you don’t know.

An Uber driver, co-worker, at the airport lounge, the person next to you on a grocery check-out line.

That’s coaching. That’s human connection. And it’s the greatest feeling to know you had the ability to connect with and help a total stranger.

Not when you’re paid. Not when you’re on stage or in a training room.

But in a quiet moment—sitting next to a stranger who’s hanging on by a thread, wondering if their life still belongs to them.

These moments don’t come because you look for them. They show up because you’re open.

That day in the airport lounge, I wasn’t trying to change a life. But I was present enough to let one open up.

Look up at people, rather than your phone. The reward is incomparable.

People are waiting for permission to believe in themselves and connect with you. That’s real.

You never know when the next conversation can change someone’s life; and yours. And all it could take is just one question.