Farewell, Musical Chairs

Here’s the uncomfortable truth: modern airline loyalty programs are built for people who value certainty, not improvisation.

Over the years, I’ve earned status with airlines I fly most often, especially United Airlines. Not because I love airports, but because status removes friction. Brings convenience. Priority boarding. Seat selection at booking. Occasional upgrades. Lounge access when connections stack up. Free checked bags. Fewer unknowns.

Those perks don’t just feel good. They change behavior.

Last December, I pulled off what I half-jokingly called a “Miles and Music” run—a strategic end-of-year journey to Austin. A push to lock in United status for 2026, and three live music shows I would have missed otherwise. A little absurd? Sure. Also very effective. It bought me another year of predictability—and convenience.

Southwest never really played that game. It asked everyone to arrive equal at the gate, then rewarded the people willing to show up earliest. If you were flexible, punctual, and liked airports, the system worked beautifully. If you weren’t, it quietly punished you.

I’ve never enjoyed hanging out at airports—or arriving too early. And while improvisation sounds romantic, it just never worked for me.

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The Tyranny of the Early Check-In

No assigned seats meant faster boarding. Faster boarding meant quicker turnarounds. Quicker turnarounds meant planes in the air, not parked at gates. The system incentivized people to arrive early, line up neatly, and move with purpose.

Operationally, it worked.

In fact, with open seating still intact, Southwest topped The Wall Street Journal’s 2025 airline rankings. Fewest customer complaints. Minimal tarmac delays. A remarkably low cancellation rate of 0.84%. They beat Delta. They beat Alaska. They beat the legacy giants.

That’s not nostalgia talking. That’s execution.

But here’s what rankings like that don’t measure: how a system feels if you don’t want to play.

Living in Southern California, I’ve flown those short hops to the Bay Area more times than I can count. San Diego or Orange County to San Jose, Oakland, San Francisco. Flights so short you spend more time in the terminal than in the air.

Southwest dominated those routes. And that’s where the friction lived.

Open seating demanded early arrival, not for security or airline necessity, but for strategy. Miss the 24-hour check-in window and you’re staring down the C group. C group often meant middle seats. Full overhead bins. Gate-checked bags. Small indignities that compound.

I don’t enjoy airports. They’re necessary waypoints, not destinations. I’d rather read at home, write, edit video, or do almost anything else than hover at Gate 23 protecting my place in line.

So I avoided Southwest. Sometimes aggressively.

Last winter, heading to Salt Lake City, I skipped a direct Southwest flight and chose a United routing via San Francisco instead. More flying. More miles. Less stress.

Why? I could choose my seat at booking. Because I could board early without gaming a check-in timer. Because I could show up to the airport later, not earlier, and still know exactly where I’d sit. With TSA Pre and CLEAR, I can usually breeze through security—in other words, show up when I wanted, not because the system demanded it.

That extra leg wasn’t a sacrifice. It was control—and control is the whole point.

When “Different” Starts to Feel Dated

For decades, Southwest built its identity on being different. Two free checked bags. No seat assignments. A sense that flying didn’t have to feel like a nickel-and-dime exercise.

To their loyalists, this felt like principle. A philosophy. A rejection of airline cynicism and status-quo thinking.

But philosophies age.

What once felt refreshingly different can start to feel like a beloved dive bar that suddenly installs Edison bulbs, adds craft cocktails, and swaps handwritten menus for QR codes. The place didn’t get worse. It just changed. And not everyone wants the old version forever.

This shift didn’t happen in a vacuum. In 2024, activist investor Elliott Investment Management disclosed a $1.9 billion stake in Southwest. Pressure followed. Profitability. Modernization. Revenue opportunities that open seating simply couldn’t unlock.

Extra-legroom seats. Preferred seats. Fare bundles with names that sound like lifestyle choices. Surveys showed what most airlines already knew: many travelers want certainty and are willing to pay for it.

Beginning January 26, Southwest joined the rest of the industry. Assigned seats. Tiered boarding. Premium rows. Less guessing.

And the changes didn’t stop there. Southwest systematically dismantled what made it distinct: ending free checked bags in May 2025, introducing red-eye flights, reclassifying its cheapest fare as highly restrictive, tightening its generous plus-size passenger policy. They added some passenger-friendly touches—free Wi-Fi for Rapid Rewards members—but the overall trajectory is clear.

Some mourned. Others shrugged. Boarding continued.

Even Southwest employees acknowledged it. One gate agent put it plainly on day one: “It’s going to be the same process as every other airline does it.”

And it worked.

Assigned Seating Doesn’t Make Southwest Boring

It makes it legible.

Legibility matters. Knowing where you’ll sit. Knowing when you’ll board. Knowing you won’t lose overhead space because you didn’t arrive early enough to stand in line.

That’s not the death of personality. That’s the removal of unnecessary stress.

I get it. Truly.

You loved open seating. You mastered it. You timed it. You made it work for you. Couples could sit together. Families could cluster. The early birds got their window seats with extra legroom near the exit rows.

For you, the system worked because you played by Southwest’s rules and reaped the benefits: two free checked bags, no seat assignment fees, and a sense of adventure in the boarding process.

Losing that feels like losing an inside joke. Or a favorite dive bar that finally got Edison bulbs, craft cocktails, and QR code menus.

But airlines don’t survive on affection alone. They survive by adapting to how people actually travel now. And most travelers prefer certainty over improvisation.

The Wall Street Journal rankings are valuable. They measure things that matter: delays, cancellations, baggage handling, complaints. Southwest excels there, and deserves credit for it.

But those metrics don’t capture the emotional cost of friction. They don’t measure the stress of setting alarms to check in. The quiet resentment of arriving early just to protect a seat. The feeling that your time is being bartered away for the privilege of avoiding a middle seat.

Operational excellence and passenger autonomy are not the same thing.

Southwest optimized brilliantly for one. It finally adjusted for the other.

A Motorcycle Traveler’s Perspective

I ride motorcycles because I control everything—the road, the pace, the stop. If something feels wrong, I adjust. If something looks interesting, I turn.

That’s freedom.

Open seating was never freedom to me. It was constrained chaos dressed up as choice. You could pick your seat, but only if you followed the rules precisely. You could bring two bags free, but at the cost of predictability elsewhere.

I’ve ridden motorcycles through regions where simply finding fuel was an adventure, where “planning” meant having a vague sense of north and hoping for the best. I’ve embraced unpredictability and spontaneity in my travels because those are often where the best stories emerge.

But when I’m on an airplane trying to get from San Diego to San Francisco for a quick trip? I don’t want adventure. I don’t want unpredictability. I don’t want to spend emotional energy worrying about boarding groups and middle seats.

I just want to sit in my assigned seat, preferably with a little extra legroom, and read my book until we land.

Some travelers loved the Southwest tradeoff. I never did.

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This isn’t a rant. It’s not a victory lap. It’s an acknowledgment.

I’m unlikely to suddenly become a Southwest loyalist. Habits and status are sticky things. But I’ll stop avoiding them. That direct flight I once skipped? If the timing works and the price is right, I’ll consider it.

Because the biggest psychological barrier is gone.

After 56 years, the musical chairs stopped.

Some mourn. Some rage. Me? I raise a quiet hand and say thank you.

Not because Southwest became like everyone else. But because it finally stopped asking everyone to travel the same way.

And in travel, as in life, that usually works better.