When Business Gets Bumpy: What Southwest’s Baggage Fee Change Teaches About Tough Business Decisions

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Blake Lively probably doesn’t fly Southwest but I bet she could kiss them on the mouth right now.

ICYMI, Southwest Airlines just did something no one saw coming: They ditched their famous “Bags Fly Free” policy and joined the rest of the airline industry in charging for checked bags.

The move has loyal customers fuming… but from a business perspective? I’m not so sure. What I do know is it’s a blessing and a curse for those of us who can see both sides of the coin.

The reaction has been intense to say the least. Longtime customers feel betrayed, with thousands of comments on Southwest’s Instagram post expressing outrage.

In what seemingly made the situation worse - they tried to be funny with their acknowledgment post and now an intern somewhere is deleting her personal Instagram and looking for a new job.

But from a business standpoint, the move was probably necessary to keep Southwest profitable in an industry where nearly every other airline has been collecting billions from baggage fees for years.

So, where’s the balance? How do we, as women in business, make the right decisions…especially when they might make some people unhappy?

I don’t know the answers, so I refer to principles that are always true. Let’s break it down:

1. Standing Out Is Great, But Only If It’s Sustainable
Southwest differentiated itself for years, but when the financial reality shifted, they had to evolve.

Lesson: If your unique selling point starts costing you more than it benefits you, it’s time to adjust. That said, customers have a right to be frustrated if they built their loyalty around it.

2. Don’t Be Afraid to Charge Your Worth
Southwest left billions on the table by refusing to charge for bags while every other airline profited.

Lesson: Are you underpricing yourself out of fear? If people value what you offer, they’ll pay. And remember: how you communicate that shift matters more than the actual shift.

3. Adapt or Get Left Behind
Markets shift. Industries change. What worked before won’t always work now. Southwest pivoted because they had to.

Lesson: Are you holding onto an old strategy that’s no longer serving you? And if you need to evolve, how are you preparing your customers for that change so they feel included rather than blindsided?

4. Short-Term Backlash vs. Long-Term Gain
Southwest knew this would upset customers, but they made the move anyway because they believed in its financial benefit.

Lesson: Sometimes, making the right business decision means upsetting people in the short term for long-term sustainability. But knowing when to hold firm versus when to listen is key. How much customer goodwill are you willing to risk?

5. Your Brand Is More Than Just One Feature
Southwest was never just about free bags—they still offer competitive fares and no change fees.

Lesson: Your brand is bigger than any one offering. Make sure your audience knows all the reasons they love you, so when changes happen, they still feel connected.

Running a business means making tough choices. There will always be moments where profitability and customer loyalty collide. The challenge is knowing when to shift, how to communicate it, and what to prioritize.

This is an opinion piece and I don’t have a dog in the fight because I am Delta loyal (no shade), but I’d love to hear what you think.

Was Southwest’s move inevitable, or could they have done something differently? How do you balance financial sustainability with keeping your customers happy in your own business?

Thankful to not be in the airline industry right now amen.

Xo, The Salesgirls