What Rankings Can't Measure

A few weeks ago, I was back in Chicago walking through Wrigleyville before the Cubs game.

I couldn’t stop talking about this dang Chick-fil-A that was recently built.

This wasn’t the Wrigleyville I remembered.

As we kept walking, I noticed a few other changes too. Tin Roof. Shake Shack. Raising Cane’s. Way too many weed stores.

Rumor has it a PBR is opening soon too. Let’s be real, no one loves having a few cocktails and riding the bull more than me, but…in Wrigleyville? No thanks.

If it weren’t for the sea of Cubs jerseys, I could’ve been convinced I was in Nashville or any other major city.

Wrigleyville felt just a little less…like Wrigleyville.

***

You see, I love rankings.

I recently spent hours on TikTok watching strangers rank the songs on Noah Kahan’s latest album.

I’ve asked ChatGPT to rank more things than I can count.

• The best wings in Denver.

• The top 10 cities I’d enjoy traveling to (this is how I started becoming weirdly obsessed with Montreal).

• The best energy drink brand for someone that wants enough caffeine to stay focused, but not enough to get jittery, plus no sugar and kind of healthy (if possible)

Before I travel, I usually already know the must-see bars/restaurants, the highest-rated ice cream shops, and the street everyone says you have to visit.

Last winter, I drove 90 minutes out of the way to ski Snowbasin.

Why? Because Ski Magazine ranked it No. 1, of course.

I’ve been trying to visit as many of Colorado’s “top” mountain towns as I can.

Steamboat. Crested Butte. Ouray, my absolute favorite.

Durango is next.

***

Rankings are incredibly useful. They reflect what people like. But they shape what places become too.

You see, rankings create incentives. Businesses notice. Cities notice. Developers notice. They begin optimizing for whatever those rankings measure.

After a while, the rankings not only measure what people value, but they begin shaping what gets built.

If every ski resort wants to become the No. 1 ski resort, what happens?

If every restaurant is chasing 4.8 stars, what happens?

If every city wants to become the go-to destination, what happens?

Some good things, no doubt. Cleaner. Safer. More walkable. More convenient. Things people consistently rank highly.

But also…more of the same.

The same rooftop bars. The same chains. The same look and feel. Those same Instagram murals that say, “I heart [insert city here]”.

Parts of Denver, Nashville, Chicago, Scottsdale, and other major cities start to blend in with one another.

Note: when I first moved to Denver I was surprised to discover places like Happy Camper, Federales, and Hampton Social. I had always thought of them as unique to Chicago.

***

Back to Wrigleyville.

It’s gained a ton of cool things in the last 10 years. Nice hotels. Great restaurants. New areas for concerts and events.

But there’s a balance between optimizing for popularity and preserving what made people love it in the first place. I fear we’re starting to tip too far toward one side.

Wrigleyville didn’t become Wrigleyville because it optimized for national appeal. It became Wrigleyville because it built its own personality over decades – shaped by Sluggers, Murphy’s Bleachers, and the local rooftops, not hotels, chain restaurants, and weed stores (ok, boomer).

But once every city starts competing to be the most popular destination, it’s only natural to borrow what’s already worked somewhere else.

Proven restaurant concepts. More event space. Other expansions.

And this isn’t necessarily a bad thing. Of course business owners will pay attention to what people like. Of course cities will want to attract more visitors.

But character can’t be optimized or measured.

It’s accumulated over time.

It’s the neighborhood bar like John Barleycorn, the old signs, the iconic rooftops, the quirky architecture you can’t find anywhere else.

It feels as if Wrigleyville became popular because of its character, then became optimized for the popularity that character created.

Makes ya think.

***

Maybe this is why I love places like Alta.

No luxury village. No snowboarders. No big apres-ski scene. It’s never tried to become Aspen or Vail or Deer Valley.

It just feels like Alta.

I had the same feeling walking around Boston recently.

The narrow streets. The old brick buildings. The history. The impossible task of finding a parking spot.

It just felt like Boston.

It had character.

Maybe that’s the key difference. Optimization increases the odds of popularity, while character increases the odds it’ll be remembered.

***

Sports might be the easiest place to see this.

The teams we remember aren’t usually the ones that were the most optimized. They’re the ones with a unique identity.

The “Greatest Show on Turf” St. Louis Rams revolutionized the NFL with an explosive pass-heavy offense before that became the norm.

The early Golden State Warriors revolutionized basketball with their three-point shooting and spacing before everyone started playing the same way.

The Moneyball Oakland A’s before, you guessed it, every team became obsessed with analytics, on-base percentage, and “solving” the game.

I think places work the same way. The ones we appreciate most have character. Charm. Something you can’t get anywhere else.

Maybe people do too.

The people I admire most aren’t always the prototypical “successful” types. They’re the ones with a strong sense of style and self. They are uniquely themselves.

And well, even if they aren’t your cup of tea, you certainly remember them.

Note: College athletics conference realignment has always bothered me, and I think this is part of the reason why too. College football used to feel like a collection of different personalities. The Big Ten runs and punts the football, the Pac-12 plays at night and puts up crazy offensive stats, the SEC is basically minor-league NFL. Mizzou and Kansas play every dang year. Now, it just feels like one giant league.

***

Don’t get me wrong, rankings are still incredibly useful.

I’ll absolutely still ask ChatGPT for the most popular burger spots when in a new city.

I just worry about what happens when everyone starts optimizing for the same thing.

Because rankings influence not only our choices, but what gets built and what doesn’t.

You see, this all really had nothing to do with Chick-fil-A.

It was just that Wrigleyville felt a little too similar to everywhere else…and a little harder to recognize as itself.

How much optimization can a place go through before it starts losing its character? Before it stops feeling like itself?

That’s what the rankings can’t tell us.

See you on the bull at PBR.