Storytelling in the sky
A YEAR OF WORKING WITH SOUTHWEST AIRLINES
I've spent years traveling. Between various storytelling series, amazing work opportunities around the world, and dating my now-wife long distance between Portland and Nashville for 3 and a half years, I've sat on a lot of airplanes.
The first flight I ever took was on Southwest. The best flight I ever took was on Southwest. The flights that took me back and forth to see my girl were all on Southwest.
Hands down, my favorite airline for years has always been Southwest.
That's why I was so blown away when the folks at Southwest said that they wanted to work together. It's been an absolute honor to spend an entire year telling stories with a jovial, ridiculous, people-focused company that I'd come to love.
This was the gig: Spend an entire year meeting incredible people on Southwest flights and sharing their stories and my adventures along the way.
I've spent years traveling the world hearing and people's stories. I've been asked to tell stories for the Pope, big brands, countless non-profits, and I even have a podcast where I share people's stories every week. I know my way around storytelling.
My strategy for collecting stories from fellow passengers was to always sit in middle seats and attempt to have conversations with the people on my right and left.
I struck out a lot. Sometimes my neighbors' headphones would immediately get placed in their ears or our conversations wouldn't go past small talk. On several occasions, I had the best conversation of my life but my new best friend was too bashful to allow me to photograph them. This project was trickier than I first thought it would be.
I've flown roughly 87 legs on Southwest in the last year. Assuming I took the middle seat 50% of the time, I sat next to roughly 135 strangers.
That's 135 times I started a conversation with a stranger. It's amazing to me how many people I genuinely connected with in meaningful ways. I even connected with a few afterwards and I still consider a number as friends.
Alongside telling stories of various passengers and employees, I also got to share some fun experiences on Snapchat in partnership with Southwest. I had a dance party on a brand new Southwest plane, gave people dares in airports in exchange for free roundtrip tickets, and sat in on a live concert at 35,000 feet! Oh, and for the month of February, Southwest included me in their magazine!
While they were interviewing me for the magazine, I was asked for advice on how to make the most out of traveling. I said, "Don't be too shy with your seat neighbor. You never know how interesting the person might be."
Meeting people on planes is a magical experience, especially on Southwest Airlines. I've found that most of Southwest's passengers are much like me: dreamers with a passion for people and new experiences that make the world feel smaller. This project taught me that flying in the sky with strangers can lead to the best conversations and I loved getting to share a number of these beautiful stories on Southwest social media.
Below you'll find a few of my favorite stories (and people) from the last year, as well as a few of my most exciting Snapchat stories!
Every Seat Has a Story
The following is a collection of a few of my favorite stories I was able to share as a part of my time partnering with Southwest. These photos and stories ran on Southwest's Instagram and Facebook.
Checking in for my flight today, I met Rebecca. She was smiling so big and making jokes as she lifted my probably too heavy bag off of the scale. She saw that I was heading to Oregon and mentioned that she used to live not too far from me. I thought she was the best and wanted to get to know her. So I started asking her questions. Why are you smiling so big? How are you so funny? How are you so strong? Do you love your job? It was a slow morning at the airport, so we actually had some time to talk.
In the 1980’s Rebecca started looking for a job in the airline industry. Not knowing exactly where to start, she started by just passing her resume out at the airport. No joke. She’d hand her information to flight attendants and pilots— anyone in a uniform, really. When Southwest called her up to interview in Dallas a few weeks later, she flew in, interviewed and got hired on the spot. She even got to meet Southwest founder Herb Kelleher.
Now how crazy is this? She’s been working for Southwest ever since. 30 years this year. She’s a pro. She says that’s why she’s smiling so big, that’s why she’s so funny, that’s why she’s so strong, and yes, she loves her job.
This was Kim's third flight ever and she was already smiling big when I sat down and said hello. As the plane took off we slowly started sharing about our lives.
Kim currently runs two daycares and she’s been doing this for 17 years. We both acknowledged the hard work that goes into starting a business.
A successful business comes from hard work and kindness, or as Conan O’Brien says, “If you work really hard hard and you're kind, amazing things will happen.” Kim works really hard at what she does. She’s driven. And she’s so, so kind.
She acknowledges that her job is hard sometimes. Discussing payments with young parents can be sensitive, working with kids is a lot of work, and rules and regulations are tricky.
She says “Even when work is hard, I have a really good life. It’ll be three o'clock and I'm swinging on a swing set, or finger painting, or eating snacks. You can’t get much better than that.” Swings, paints, and snacks— that’s how you know your hard work has paid off.
Waiting for my boarding group to get called I looked over my shoulder and saw a familiar friendly face. Maybe one of the most friendly faces I’ve ever encountered. It was @jedidiahjenkins.
Jedidiah is an adventurer in the truest sense of the word. He’s a traveler (he biked from Oregon to Patagonia a year ago), a writer (he’s in the middle of writing a novel), and a world changer (he worked closely with a non-profit that changed lives for countless people in Central Africa).
I’ve looked up to Jedidiah for a long time, interacted with him a few times, and even interviewed him on my podcast a few months back. I was so excited to randomly bump into him on my flight.
We got to spend several hours together— from boarding in Nashville to our layover in Phoenix— talking about Jedidiah’s great adventures, the hopeful things happening in the world, and how we always seem to sit next to the most interesting people in random situations like a little Southwest flight.
The other day I was flying through Baltimore and met Savanna. Savanna started working in a salon at 17. At 19, she knew she wanted to try something new so she applied to work for Southwest.
She said she wanted to do something fun and travel at this time in her life.
I wanted to know if having a fun job and getting to travel only applied to “this time in her life” so I asked if she thought she’d be sticking around.
She said she was sure she was going to be sticking around for a long time.
Seems like a pretty cool job to me.
Some people have a way about them that can light up the room (or a plane).
David might just be the friendliest guy I’ve ever met. He warmly said “hello” with a smile on his face when I sat down. And while we were buckling our seatbelts, he kindly told me and the person sitting next to me a short funny story.
During our flight we got on the topic of what we spend our time doing. David works in the medical field but has hobbies that run the gamut. He’s traveled all over the world and we even discovered we've been to a handful of the same places.
The more I got to know David, the more I could tell that his many hobbies and interests outside of his profession make him even more passionate about his job itself. When you’re passionate about your work, often that passion spills out into your life and the people around you.
During that flight I got to experience David’s passion for life first hand through his stories and the way he carried himself.
You embody passion well, David. Thank you.
We had just boarded our flight from New York City to Nashville when I asked her if she was from Nashville. She asked me if I was from New York. We both guessed wrong, but it got our conversation going.
Rachel told me she always imagined she’d move to New York one day, though at the same time never thought she actually would. But just three months ago she packed up her life in Seattle and headed to Manhattan for an amazing new job. She told me she was already loving it.
I briefly mentioned to Rachel that I used to be a wedding photographer and she began to tell me about her dreams and ideas to one day work in the wedding industry in a unique and meaningful way. She told me about what she loves about her current job and about how she hopes to grow in the coming years and maybe even start her own company one day.
And from that moment on, Rachel and I were friends. When we parted ways Rachel and I exchanged email addresses in the hopes we’d be able to help each other out down the road.
If there’s one thing I’ve learned through flying, sharing a small detail about yourself could be all it takes to be the start of a friendship. Thanks for reminding me of that, Rachel.
When I sat down next to Blake on my flight to Denver, something told me he had an interesting story to tell. We started off by talking about the normal stuff you talk about on a plane— the weather, where we’re traveling to and from, and eventually, our jobs.
When we reached the jobs part of our conversation, we really connected. Blake told me that he and his brother just started their own company together. They took their background working in roofing and construction and started up their own restoration company in Denver.
As somebody who also started and owns his own business, I was immediately fascinated. I started asking questions. “Isn’t starting your own business crazy scary?” “Isn’t starting your own business the best?” “Are you an LLC?” “How are you finding clients?” You know, business geek stuff.
And for a lot of the flight he and I talked about starting a business— how it’s so hard but so worthwhile.
He said it’s been a year for change. In the same year he quit his job, got a dog, bought a house, and started this company. That’s pretty amazing.
When I saw Ann holding this rose balloon, I knew I had to say hi. I walked up to her and told her I -loved- her balloon. She smiled and told me all about the balloon artist in the Southwest terminal (apparently Southwest brought in a balloon artist for Spirit Week!).
She’d walked up to him and told him her sister was sick, and she wanted to bring her something special.
The artist said he knew just what to make her and immediately got to work on this Beauty and the Beast style balloon rose.
With tears in her eyes she told me it was perfect. Her sister’s favorite flower is a rose and her favorite color is red.
Then Ann told me that her sister had been diagnosed with a brain tumor a year ago. And that she was on her way out to Pennsylvania to surprise her and cheer her up. That’s when my eyes filled with tears.
Ann and I got to talk for a few more minutes. She told me more about her family and told me that her favorite hobby was flying kites. When it was time for her to line up to board, we hugged goodbye, I wished her a great trip, and she joyously boarded her flight.
The Adventure of Travel
The following is a collection of a few of my favorite Snapchat stories I got to make with Southwest over the last year. I greatly admire their love for fun, celebration, surprise, and people. I'll never forget these particular adventures.