
Getting Out of Your Comfort Zone
I remember it like it was yesterday. The date was January 2, 2002. I peered through the window of my airplane, taking in the sights
“I think he’s about to throw up!” the father of a young child blurted out behind me.
We were standing in line on the tarmac, waiting to board a Southwest Airlines flight to Tampa. It was an early Friday morning, and the plane was packed for the 5:00 a.m. departure. The cabin was filled with families eager for Florida’s warm weather, theme parks, and a major baseball tournament. There wasn’t a single empty seat in sight.
I was on a quick trip to attend the wedding of Darren, one of our Northern Colorado Jiu Jitsu professors. He had recently moved to Florida to marry his middle school sweetheart. I was genuinely happy for him and looked forward to a brief escape—some much-needed time for myself and a change of scenery.
The months before this trip had been exhausting. Life and business were moving at a fast pace, packed with long days that started before sunrise. Despite reminding myself that I was fulfilling my purpose and calling, the reality was:
I was drained—low on energy, patience, and kindness.
I was running out of the ability to contribute to others in a positive way, because my cup was almost on empty.
As I was running out of these good things, I could feel myself slowly filling with and defaulting to anger, frustration, and absolutely zero patience. Emily often points out how my smile fades into a serious, stern glare—what she jokingly calls my “resting serious face.”
I couldn’t wait to get on that plane, sleep for four hours, and recharge. The seemingly endless wait on the tarmac was finally coming to an end. With only three people in front of me boarding the plane, I noticed there was a front row aisle seat open!
“YES!” I celebrated. I love the front row for several reasons. A little extra leg room, I get the first drink and pretzels, close to the bathroom, first off the plane, and typically I get to interact with the flight crew, who on Southwest flights are usually very enjoyable, funny and kind.
But…
“He is going to puke!’ exclaimed dad again.
These comments by dad were interjected in between the universal sounds and body language his son was presenting, signaling he was about to show me his breakfast, right there on the tarmac. As the moment of truth arrived for this adorable young boy, I noticed a trash can in front of me. I motioned for dad to bring his son to the trash can, and there he threw up.
I turned back around to enter the plane and was greeted by a young woman named Shannon, one of the flight attendants. I was then greeted by this man’s son again as he was preparing for round two of the vomit session. Shannon grabbed the boy a trash bag as he, his father, Shannon and I tightly danced around the airplane entrance attempting to avoid catching breakfast, and then, finally:
Front row, aisle seat!
I grabbed a seat, settled in and then…
I passed out.
During one point of the flight, I woke up. Working next to Shannon was another young woman named Kay. At one point during the flight we began chatting it up. They noticed my Northern Colorado Jiu Jitsu and Self Defense t-shirt, and we began conversing about what I did professionally, my family, and the upcoming few days in Florida.
I dozed off again, then woke up.
Each time I opened my eyes, I found myself drawn to something. Kay and Shannon stood out with their warmth, kindness, and genuine friendliness as they served passengers. I knew Southwest Airlines is known for its fun atmosphere—witty slogans, lighthearted jokes, and a focus on customer experience. But these two went beyond that. They truly cared about people. They didn’t just create a lively atmosphere; their interactions with each other were sincere and uplifting, spreading positivity across the cabin.
I passed out again.
I woke up again as Kay and Shannon began poking holes in the ends of some Southwest pretzel bags. They were laser focused on stabbing these bags precisely in the four corners so that they could then pass their iconic Southwest red, plastic, heart topped coffee stir sticks through the bags. I asked what they were doing, and they shared.
“SHHHHH! We are making a birthday crown for the 12-year-old girl sitting behind you.”
“Hey ladies,” I interjected. “Can I take a picture of this crown?”
I told them I was working on my next business book and that their actions were not only inspiring but also a powerful story worth sharing. Their kindness perfectly illustrated a principle I deeply value—something all successful businesses have in common and what we, as people, are naturally meant to do:
Pouring Into People.
I explained the concept to them and thanked them for their hearts and kindness towards the little girl. They agreed I could take a photo of them and the crown and then told me:
“Wait until you see what we do with this crown at the end of the flight.”
“Hey, can we make you a crown, Matt?” asked Shannon and Kay.
I told them if they did, I would display it in my leadership library at the Sevilla Center.
I passed out again. I woke up again.
Shannon and Kay were intently punching small holes in more pretzel bags. They looked at me over and over, more specifically my head, to determine how many bags this crown would need. Just a few minutes later they gifted me the crown.
“Happy Father’s Day, Matt!” They stated.
When they told me this, it warmed my heart. I began to fight to hold back tears. At that moment I realized how tired I was, how drained I was, how much patience and kindness I had recently been lacking, and that I was approaching Father’s Day on Sunday. All these ladies did was make a silly little crown and tell me Happy Father’s Day. At first glance, it was just a simple crown made of pretzel bags and plastic stir sticks—right?
Wrong.
This small creation reflected something Shannon and Kay understood well. It was a reflection of their thoughtfulness and a reminder of what truly drives every successful business: PEOPLE.
More specifically, relentlessly pouring into them.
Shannon and Kay, whether they knew it or not, were naturally were working through a simple process that creates and builds successful and impactful companies.
They followed the Pour Into People Process by:
Example.
I woke up with a jolt as the plane touched down in Tampa. As we taxied and prepared to exit the plane, Shannon and Kay completed step 4 by getting on the intercom, announcing this girl’s birthday and presenting her with the crown. Turns out she was an unaccompanied minor and was traveling with some friends for her birthday. The passengers applauded, the girl’s eyes sparkled, and I left the plane holding my own crown.
I enjoyed the weekend at Darren’s wedding and flew home on Father’s Day morning to be with my family.
The Sunday morning Father’s Day flight back to Denver was very early and not as eventful as the flight to Florida. I slept on the plane, it landed smoothly, and I exited.
As I was exiting a moving walkway, I jumped off and landed right next to…
Shannon and Kay! I stopped to say hello, and they were very happy to see I was holding my Father’s Day crown. We chatted quickly, they wished me Happy Father’s Day again, and then, whether they knew it or not, they executed on the Pour Into People Process.
They walked over with me to the end of the gate area overlooking the lower level of DIA, and posed for a photo. They presented me with my Father’s Day crown in a king like fashion. It made my day, and warmed my heart all over again.
In life, leadership, and business, your actions influence others—whether you realise it or not. Every day, your story intersects with theirs, offering a chance to make a positive difference. Never forget the importance of investing in people. Remember to Pour Into People.
Kay and Shannon, thank you for showing what it means to truly care for others!
I remember it like it was yesterday. The date was January 2, 2002. I peered through the window of my airplane, taking in the sights
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