Ailana’s Journal—2026-09-05 (and Island Kids) (Patreon)

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GOOD MORNING by Ailana Geven Keller

Saturday has arrived, and I’m ready for a good day. Everyone is excited to share some things with you, but I want to pick up on the Chicago history I promised to share.

Yesterday, we looked at how it went from a trading post to a small settlement in 1833. Today, we’ll look at what happened next.

Chicago became a city in 1837, but almost immediately ran into trouble. A national financial panic hit that same year, slowing construction and sending land values down. The little city kept going, though, and by 1840 it had grown to more than 4,000 people.

Then came 1848—a pretty remarkable year for Chicago.

The Illinois and Michigan Canal finally opened, creating a water connection from the Great Lakes through the Illinois River system to the Mississippi. Chicago was suddenly sitting between eastern markets and the huge agricultural region developing to its west.

That same year, Chicago’s first railroad began operating, telegraph service arrived, and the Chicago Board of Trade was founded. The city was becoming a place where grain, lumber, livestock, manufactured goods, money, and information could all move through quickly.

And people followed.

Chicago had nearly 30,000 residents by 1850. During that decade, rail lines spread outward in almost every direction, tying farms and towns across the Midwest to the city. By 1860, the population had climbed past 100,000.

That is an astonishing amount of change in about twenty years.

What started as a small settlement beside a muddy river had become one of the country’s great transportation and commercial hubs—and it was nowhere near finished growing.

I think that’s enough history for breakfast. Tomorrow, we’ll keep moving forward.

Right now, we’re heading out. Nothing brilliant is planned, but we want to visit Millennium Park and Michigan Avenue so stick around!

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BEAN AGAIN PLUS ONE by Kel Ryan

This was sort of my idea. When I came to Chicago a few months ago, we posed here for a family picture. I thought we should do that again.

Aria seems to be pretty happy about everything. But I get the idea she’s still a little scared and trying to find out what to do and when to do it.

I keep telling her to chill and not worry. She keeps telling me okay, then continues to worry anyway. But I guess that’s fine.

Like, she’s eight, and no one has ever lived up to her hopes. I know the family that was trying to adopt her—the Fletchers—would have, but that unraveled fast. Cancer…

But Josh and I sat down a few weeks ago and he said that if anything insane happened, his family would step up and take care of me until I turned eighteen. He said all the AGI people would help. I could live with Clay and Sasha or something.

Bottom line, he said for me not to worry. Now, with Aria along, it’s more complicated, but the same foundation is there. The Ryan family and all of the AGI people…

Plus, I’m sort of counting on the odds. I know things could happen, but usually, they don’t. Usually, families carry on. Parents become grandparents, and sometimes great-grandparents.

But I get why Aria is cautious. And it’s hardly been any time at all, right?

I guess I’ll have more to say on this later. Meanwhile, we’re going to get snacks and make our way to Michigan Avenue—specifically the Magnificent Mile.

See you next time!

MAGNIFICENT MILE by Emily Amos

The Magnificent Mile is a stretch of North Michigan Avenue in Chicago famous for shopping. There are stores here from all over the world—famous brands and all that.

I’m just a kid, so take my opinion for what it's worth: overrated.

I thought I’d do a Roadside Yawn Meter article, so here you go…

Roadside Yawn Meter: The Magnificent Mileby Emily Amos and Kel Ryan

Yawn Factor: High—8 out of 10

Kid Verdict: Total Yawn: If you really love shopping, you might disagree with us. Otherwise, it’s a long stretch of stores, restaurants, hotels, traffic, and people spending money. Lots and lots of money.

Best Part: The people-watching is pretty good, and some of the buildings are worth looking at. It’s also right in the middle of Chicago, so walking along Michigan Avenue can get you from one actually interesting place to another.

Boring Part: Shopping. We know that sounds stupid because shopping is basically the point, but most of these stores sell things you can buy somewhere else. Except here you can apparently enjoy paying more for them while carrying the bag down a famous street.

Also, nobody puts “occasional smell of alley garbage” in the tourism advertisements. We checked.

Parent Warning: Your kids may want things. You may want things. Everybody around you will be carrying bags containing things. This entire area seems specifically designed to convince human beings that they require additional things.

What Would Make It Better: Fewer stores pretending expensive automatically means interesting. More public spaces, weird local stuff, art, or anything that gives you a reason to stop besides buying something or eating something.

Kel’s Photo Note: It photographs better than it experiences. Look up instead of into the windows. The architecture, signs, crowds, and long views down Michigan Avenue make much better pictures than another rack of clothes.

Emily’s final advice: Buy a charging cable you actually need, take a picture proving you were here, and mark “shopped at the Magnificent Mile” off your bucket list.

Then go find Chicago.

GOOD NIGHT by Ailana Geven Keller

I was assigned to sit here while Jason, Jasmine, and Emily use the restrooms to wash their hands. Kel is behind the camera.

We’re at Ed Debevic's, a retro-style restaurant not too far from the Ryans’ home. It’s just the five of us here.

Sasha reported that Bump was tired and wanted to go home. She asked Aria if that sounded like a good idea, and Aria agreed.

I want to follow up on Emily’s thoughts about the Magnificent Mile. She and Jasmine were talking in the car.

“It seems like it’s just all about material things,” Emily said. “Like, is a $250 blouse that much better than a $70 blouse?”

“You’re paying for the brand name,” Jasmine replied.

Clay added a thought. “Aside from the brand, high-end items ought to come with better materials, construction, and quality control. I’d say the $70 blouse is probably better made than a $20 blouse that looks the same.”

“How much is that better quality worth, though?” Emily asked.

She held to her views. She believes that there comes a point when you stop paying for something that's notably better and start paying for its popularity.

“I could buy a month’s worth of clothes at the thrift store for the cost of one outfit in some of those stores.”

And therein lies the root of her opinion.

I don’t have $250 blouses myself. I do have some shoes that were expensive and that I’ll have for years to come. Jason has a pair of black dress shoes he paid $300 for a decade ago.

There’s a balance, I think. A $10 blouse might last through a couple of laundry cycles. A well-made $50 blouse might last a lot longer. I suppose you see the point.

I think where I end up is this: use money to get things you need that will last. And then use money to create memories with people you love.

May you spend wisely on what lasts—and generously on the people and moments that matter.

Good night.

Be your best you!

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