Last week, we took Dewey on his first flight so I could do a keynote for HR Source. We planned to travel Sunday, but nature had a different idea. The forecast said 90s with 25 mile per hour winds for the weekend. Plans had to change. We can’t just lock ourselves in our van during a 100 degree dust storm. We would cook.

There was one flight option direct to our destination and it took off in less than 24 hours. We booked it. This gave me very little time to worry about Dewey getting on his first flight. We had less than 15 hours to pack and get the van ready to sit in a parking lot for two weeks in extreme heat. By the time we went to bed that night, I didn’t even have the energy to be anxious.

When we got to the airport, Dewey really surprised us. He was very well behaved despite the chaos of Vegas. Everyone at the counter told us how cute he was. As we walked toward security, I overheard a guy wearing a Chicago Bears jersey just a few agents down raising his voice. “We don’t take cash,” the woman explained sternly. We were on one of those budget airlines where they charge for everything – even a boarding pass. He said something I didn’t hear as I walked away, stressing about the dog.

The moment I had Dewey under the seat, I let out a big sigh of relief. My row was empty and we had intentionally waited to board last. “Maybe I’ll get the whole row to myself,” I thought. I should have known better. Never celebrate an empty row on a plane until the door is closed.

A few minutes later, a masked, short, 60ish year old man got into the middle seat. As a frequent (and tall) traveler, that’s a win for me. Then, I saw the man in the Bears jersey from the gate.

I recognized his look from the Vegas strip. Tan, worn skin. Missing teeth. He smelled strongly of alcohol and cigarettes, his nails were filled with dirt. Every time I have visited Las Vegas, I’ve seen at least 10 guys that look just like him. “With my luck, I bet he is sitting here,” I thought, clearly not applying my new found commitment to optimism.

As I stood to let him in the row, we made eye contact. “Can you put my bag up? Thanks!” he blurted as he climbed in. As we pulled off the gate, Dewey settled down but my new aisle mate just got more agitated. He reached up to the button that calls the flight attendant. “Where’s the air sick bags, I’m going to puke,” he said when she neared the aisle. The discomfort that immediately washed over every aisle within earshot was palpable. I’m sure they were thinking the same thing I was: it’s about to be a very long two hours and forty three minutes.

I leaned forward to make eye contact with my new seat mate. “When we get in the air, I have Dramamine I can give you for the nausea. I get air sick too.” As I waited for the plane to reach altitude, I asked another question to help distract him from the clearly anxiety-induced nausea. “Do you like rollercoasters?” He smiled a little and said, “I did go to Six Flags once.” I shared my trick for nausea. See, oddly enough, I love rollercoasters. Hate turbulence. I close my eyes and pretend I’m on a rollercoaster when I feel sick. It helps.

When I gave him the Dramamine, he rang the attendant bell again and the clearly annoyed flight attendant appeared. “I need to take this pill,” he said. I saw the look in her eye – the one that said she thought he was using on a plane. I quickly spoke up. “For motion sickness. I gave it to him. It’s Dramamine and he needs water. Please.” She gave him another disgusted look before walking away.

Over the next few hours, I learned his name was David. He fell about four months ago and had 57 staples in his head when he woke up. He grew up skateboarding. Had many jobs – cable guy, construction worker. He did the framing on his own mom’s house. He has a seven year old daughter named Riley. His stepdad died last week. He was on a one way flight home to try and figure out his life. “I’m an alcoholic,” he said with so much shame that I just wanted to hug him. We also figured out that the wife of the very kind-hearted gentleman in the middle seat was the one who paid for David’s boarding pass.

Honestly, I didn’t want to talk. I was worrying about Dewey. Judging this stranger. Turns out, he had a lesson for me.

About halfway, David thought he lost his wallet and started to panic. “I only have $100,” he said. “Please. We have to find it.” After he did, the first thing he did was hand the guy in the middle seat $5. “Thanks for your help man.” The middle seat refused. “You keep it, buddy.” When David found out how much Dewey loves frisbees, he reached in his bag and handed me a tiny yellow frisbee. “He can have this!”

As we all got off the plane, we said quick goodbyes. I went down to baggage claim to wait and I saw David again while I waited for our bags. He walked up and handed me a stick of beef jerky. “I know it isn’t much, but I wanted to say thank you for being nice to me.”

“You don’t have to do that,” I said. “We’re all supposed to be nice to each other, remember?” That was another topic we covered on the plane. Realizing he wouldn’t take it back, I smiled. “Do you want to see how happy Dewey is to see his new Frisbee?”

That night when I got into bed, I caught myself opening Instagram to try and find my new friend. I wanted to tell him thank you for the lesson in generosity. Here’s this guy who can fit everything he owns into a carry-on and backpack. He was more generous than some of the most wealthy people I know. Most of them would never offer to pay back $5. They’d never consider getting a gift for someone that was kind to them on a plane.

I learned a lot more than how to fly with a dog on that plane. I was reminded of some lessons that make the world a lot more enjoyable. That kindness is free. That I don’t need a lot to be generous. That a conversation on a plane could be just the thing I need to see the good in the world again.

Weekly Letters generosity kindness