Friends,
I have been thinking a lot about Southwest Airlines today. I am flying them tomorrow, and that feels fitting, because they are right in the middle of one of the most important seasons in their history.
It has been about a year since Elliott Management bought just enough of a stake in Southwest to begin pushing for big changes. Since then we have seen the first layoffs in company history, cuts to company-wide culture events, quiet downgrades to Rapid Rewards, and announcements about assigned seating and possible long haul flying. Oh, and bags don’t fly free anymore.
The people at Southwest are still incredible. The direction at the top is much less clear.
In today’s podcast, I talked through why that matters. Delta and United are capturing the vast majority of the industry’s profits by moving up market and building a felt premium that customers will pay for. Southwest, on the other hand, risks drifting toward a space that looks more like the ultra low cost carriers (who are hemorrhaging cash), without a clear premium strategy and without leaning fully into the cultural superpower that made them exceptional in the first place.
I want them to win. I believe in the people there. I am a shareholder (however poor of an idea that might be). The question is whether the leadership team will decide to build something worthy of what Southwest has been.
It feels like that old Taoist story where the kid gets a horse, then loses the horse, then breaks his leg, then doesn’t have to go to war… and every time the farmer just says, “we’ll see.”
That’s pretty much where we’re at. We’ll see.
On a more positive note, I saw an ad for an Antarctic cruise and it reminded me why that trip sits so high on my list. It is one of the last true expedition style itineraries you can book, a chance to feel the size of the world and the wildness of creation in a way that is hard to put into words. Not on the budget this year, but it is worth having in mind and planning toward.
Closer in, I am actively working on spring break plans for our family. The current idea is to route through New York, overnight near JFK, and then take one of the few daytime flights to London with the girls in economy on points. There is great transatlantic award space right now, and it is fun to build a trip that lets us cross the ocean together without paying cash. Yahtzee.
Underneath all of this, what keeps coming back to me is the simple question of what makes great service great. Yesterday I wrote about that Delta flight to Cape Town, where the crew found two lost passports and pulled the aircraft back into the gate so the couple could reboard and make their once in a lifetime trip. That is not policy. That is empathy in the best way.
Travel pulls all of us out of our normal patterns. It creates a thousand chances every day to either shrug and move on, or to step in and care. The airline industry is one of the hardest businesses in the world, but it is also one of the clearest windows into how leadership, culture, and simple human kindness show up under pressure.
My hope is that when you travel next, you experience that kind of care and that you get to extend it to someone else along the way.
Fly well.
