Southwest Lost Its Why—and It’s Losing Its Way
At the Esteemed MBA, we teach three foundational pillars:
The deliberate actions required to manage people well
The practice of Followership—earning trust through humility and integrity
And the deeper, often messier, work of shaping and sustaining company culture
I try to use real-world examples to bring those principles to life. And sadly, this one hits too close to home: Southwest Airlines has lost its way—because it lost its Why.
The Culture Triangle
We often talk about three books as the foundation of company culture:
Start With Why and Leaders Eat Last by Simon Sinek
Good to Great by Jim Collins
Sinek teaches us that culture starts with a reason for being—the Why. Leaders Eat Last adds the “Circle of Safety”—a culture where people feel protected, trusted, and aligned. Collins’ Hedgehog Concept (from Good to Great) tells us to sharpen our focus: be clear on what you do best, what drives your economic engine, and what you’re deeply passionate about.
Think of the Circle of Safety as a physical space—lined with core values that create security and belonging. But inside that circle, you’ve got to fill it with clarity:
Where are we going?
How will we get there?
Who’s responsible?
Why does it matter?
That last one—the Why—is everything.
Remember Herb Kelleher?
Southwest’s founder, Herb Kelleher, understood this decades before Simon Sinek gave it a TED Talk. Herb scribbled Southwest’s purpose on a cocktail napkin:
“Travel for the common man.”
And their Why? Just one word: “Love.”
Everything Southwest did passed through those two filters. If a new idea helped deliver affordable travel for everyday people, they did it. If not, they passed. If it showed love to employees and customers, it stayed. If it didn’t, it got cut.
This philosophy shaped every decision:
Peanuts instead of full meals
Open seating to keep things simple
Fast turnarounds to keep planes in the air
No fees for bags, transfers, or cancellations
Jokes from flight attendants. A little fun. A little weird.
Southwest was fun. It was different. And it was profitable. Herb believed in his people so deeply that he’d side with employees over customers. He walked tarmacs and terminals asking mechanics and ground crews how the company could better serve them.
It worked. Until it didn’t.
And Then They Lost It
Today, Southwest is… like everyone else.
Bag fees? Check.
Assigned seating? Check.
Higher prices, confusing options, a drop in service? Check, check, check.
They bent the knee to the same playbook followed by Spirit, Frontier, and every other race-to-the-bottom airline. They forgot who they were. They let go of the culture Herb built. The Circle of Safety is cracking—and the Why is gone.
Apple Did the Same—Until They Didn’t
This reminds me of Apple in the mid-90s.
Back then, Apple licensed out its operating system to other hardware companies like UMAX. Why? Because Microsoft was dominating by scaling software installs. So Apple tried to copy that model.
Then Steve Jobs came back.
His first move? Kill all those contracts. Take back control. Make Apple the sole manufacturer of everything with an Apple OS. As a tech analyst at the time, I thought the decision was suicidal.
But Jobs wasn’t chasing short-term metrics. He was reclaiming the Why. He wasn’t just rebuilding a company—he was thinking different. He was getting back to making insanely great products. To putting a dent in the universe.
Mark My Words…
In ten years or so, a Herb disciple will take the helm of Southwest.
And their first moves will sound familiar:
No more assigned seats
Bags fly free again
Flights pulled off third-party travel sites
And most importantly—employees at the center again
They’ll remember the Why. And they’ll rebuild Southwest with Love at the heart of the business.
What’s the takeaway for us at Esteemed?
Culture isn’t fluff. It’s not perks or posters or values written on a wall. Culture is clarity. It’s the consistent alignment of every decision with a deeply held purpose. It’s the safety you build for your people—and the fire you light to move them forward.
When companies forget that, they lose their way.
Don’t forget your Why.
Be Esteemed. Lead with Purpose.
