Why That Worked – Presented by StoryBrand.ai

#32: Southwest—The Genius of ‘Bags Fly Free’ and What Happened When It Changed (RE-RELEASE)

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Aug 11, 2025

Explore Southwest Airlines' branding brilliance and the fallout from their decision to end the 'bags fly free' policy. Discover how this change has impacted customer trust and brand identity. The discussion dives into the challenges of communicating sensitive changes in the airline industry while emphasizing the necessity of clear, engaging messaging. Learn about the importance of loyalty, customer understanding, and effective communication strategies in fostering lasting relationships and successfully navigating market shifts.

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INSIGHT

Bags Fly Free Built A Clear Identity

Donald Miller praises Southwest's playful, memorable messaging.
Their "Bags fly free" promise created a clear, defensible brand identity.

ADVICE

Publish A White Paper To Show Your Work

Donald Miller advises releasing a white paper to explain board-level decisions.
Let press and thought leaders see the rationale so they can contextualize the change.

ADVICE

Don't Use Humor For Price Hikes

Avoid humor when announcing price increases, Donald Miller warns.
Humor fits discount brands but fails when you must justify higher costs.

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Hopefully you're getting a chance to recharge this summer—but that doesn’t mean you have to lose momentum. Fall is just around the corner, and before you know it we’ll be heading into the final stretch of the year. That’s exactly why we’re rereleasing several of our high-impact episodes—designed to give you clarity, sharpen your message, attract the right customers, and ultimately drive more revenue, so you’re not stuck playing catch-up when it matters most! --

Southwest Airlines built one of the strongest brands in the world by doing one thing better than almost anyone: clear, clever messaging that made customers feel like family. “Bags fly free” was more than a tagline. It was a promise that set them apart from every other airline. But when they recently backtracked on that core message, the backlash was instant. In a world where loyalty is fragile and expectations are sky-high, even the best brands can stumble if they don’t communicate the right way. So what happens when a company known for brilliant messaging gets it wrong?

In this week’s episode, Don and Kyle unpack the marketing brilliance that made Southwest an iconic brand and why their latest messaging misstep is such a big deal. They reveal how Southwest’s playful, people-first branding created an unbeatable bond with customers, and how this new shift risks breaking that trust. You'll learn what Southwest could have done differently, why your messaging must evolve without abandoning what made you great, and how to communicate tough changes without losing customer loyalty. Tune in to find out how even a beloved brand can slip and how you can avoid making the same mistake.

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