Was this essay forwarded to you? Join for Free Here

I can easily recall walking through Charlestowne Mall as if it was yesterday.

Waldenbooks. FYE. American Eagle. Abercrombie. Hollister. KB Toys. The Disney Store. Auntie Anne’s. Mrs. Fields. Von Maur. Spencer’s and Hot Topic were there too, though they were strictly forbidden territory.

We could ride our bikes there or walk. I honestly do not know how much we actually did either, but we could have. That fact mattered.

While I am a Millennial and not Gen X, I did catch the tail end of the benefits of being born in that time, in that place, with lingering 80s tendencies still bleeding into the 90s and early 2000s.

There was still trust.

I remember one time my dad bringing me and my friends to the movies and dropping us off. I want to say we were in middle school. As we loaded out of my dad’s 1999 Nissan Maxima he gave instructions, told us when and where to meet him in a few hours, and left.

That was a small act of trust. Not dramatic trust. Not reckless trust. Just ordinary trust. The kind of trust that used to be built into growing up.

You had a few hours. You had some money. You had your friends.

And you had to figure some things out.

If you have been here for any length of time, you know one of my core frameworks is the Generational Pendulum. We see a generation experience something, often challenge it, then overcorrect and rebel, and eventually recalibrate to a new normal.

Part of the theory analyzes how certain trends may skip a generation or two, then resurface in a new form. We saw that with the idea of the “me” generation, first attached to Boomers, then resurfacing in a different form with Millennials through filters, feeds, and carefully curated lives online.

Now we are seeing another swing, and almost a reflection, between Gen X and Gen Z.

A year ago, one of my earliest Collide essays looked at Barnes & Noble and the surprising return of physical bookstores. At the time, it felt like a curious cultural signal. A generation with every digital convenience available was choosing paper, shelves, browsing, cafés, and the slow pleasure of discovery.

Now it feels like part of a larger pattern. USA TODAY recently covered Gen Z’s role in the mall resurgence, pointing to young shoppers who are not simply buying in person but gathering in person. The story drew on Lightspeed research showing that 83% of 18-to-24-year-olds say social retail environments improve their sense of connection, 68% say they would spend more as a result, and 75% say “third spaces” like cafés, lounges, or social areas inside stores matter when deciding where to shop (Lightspeed, 2026). 

That is not just a retail trend. That is a trend towards returning to in-person community.

Placer.ai’s 2026 mall report found that indoor malls and open-air centers have seen consistent year-over-year visit growth over the past two years. Indoor malls, in particular, are functioning more like experiential third places, with 37.6% of indoor mall visits in 2025 lasting more than 75 minutes (Placer.ai, 2026). 

Starbucks seems to be reading the same cultural signal. After years of mobile ordering, pickup shelves, drive-thru lanes, and transactional convenience, the company is trying to restore the coffeehouse as a gathering place. Starbucks says more than 1,000 coffeehouses will be “uplifted” by the end of 2026 with warmer, more comfortable design, more seating, and familiar comforts meant to make stores feel like places to linger (Starbucks, 2025). 

The old story was that everything physical was dying.

Bookstores were dying. Malls were dying. Cafés were becoming pickup counters. Winning at the retail game was no longer window displays and clever merchandising and loss prevention, it was all about shipping logistics, cost cutting, and delivery speed. 

Gen X, born 1965 to 1980, came of age with a kind of independence that feels foreign to many parents today. They were the latchkey kids. The MTV kids. The mall kids. The kids of divorce, recession, institutional disappointment, and “figure it out.” Pew once called Gen X America’s “neglected middle child,” which is both a demographic observation and a fairly accurate cultural mood (Pew Research Center, 2014). I often refer to them as the same or call them the "barbell generation."

Gen Z, born 1997 to 2012, also grew up skeptical. But the source of the skepticism was different.

Gen X was rarely watched. Gen Z has been over-watched.

Gen X came home to empty houses. Gen Z had their movements tracked, even in their houses.

Gen X disappeared into malls. Gen Z was location-shared into structured activities.

Gen X learned social rules by bumping into them. Gen Z learned social risks by watching them get recorded, posted, mocked, screenshotted, and stored forever.

That is not a small difference, it is a formative one.

Americans trust each other less than they did a few decades ago. Pew Research Center reported that the share of adults saying “most people can be trusted” declined from 46% in 1972 to 34% in 2018, according to the General Social Survey. Pew’s own 2023 to 2024 polling found the same share, 34%, saying most people can be trusted (Pew Research Center, 2025). Gallup and the Walton Family Foundation also found that Gen Z has low confidence in major institutions, with Congress, the news, the presidency, and large technology companies drawing especially low trust (Gallup, 2023).

So yes, Gen Z is skeptical.

But their skepticism is not simply Gen X skepticism in a hoodie.

Gen X looked at institutions and said, “I do not trust you, so I will take care of myself.”

Gen Z looks at institutions, platforms, employers, schools, brands, and sometimes even peers and says, “I do not trust you, but I also do not know where else to go.”

That is the difference. When Gen Z had distrust, they just switched from one social media influencer to the next, but never anchored to anything in real life. Gen X, on the flipside had their best friends, their community, their neighborhood...a real physical grouping of people they could connect with.

Boomers and Gen Xers remember being put “on restriction” or as the term aged, “grounded.” Many Millennials, myself included, do too.

Being grounded meant you could not go anywhere. You could not do anything. You were remanded to the confines of your room.

You could not go to the mall. You could not ride your bike to a friend’s house. You could not go outside on a nice day. You were stuck at home, and that was the punishment.

For much of Gen Z, that restriction has often felt less like a punishment and more like the baseline.

I do not want this to become an essay blaming parents. Parents were responding to real fears, real headlines, real risks, and a world that felt less predictable. The technology also changed the equation. If you can know where your child is at every moment, many parents feel irresponsible not using that tool.

But safety has consequences too.

There is no sneaking out under the bleachers with your significant other because there are cameras there, and you are being tracked on a phone. There is no walking down the mall and having that girl grab your hand for the first time in quite the same way if the parents are two steps behind you, or if the relationship has already been arranged, endorsed, monitored, or vetoed through layers of adult awareness.

Of course, some of this sounds better. Safer. Cleaner. More responsible. But growing up has never been clean.

Kids need some awkward. Teens need some uncertainty. Young adults need some spaces where they can try on identity without an adult (or media and algorithms) narrating the whole thing.

Gen Z is not becoming Gen X. History does not repeat itself that neatly.

Plus, Gen Z is almost too old. Gen Z is currently between 14 and 29 years old. Only the last few Gen Zers born might be able to enjoy this new experience, but that gives us great hope for Gen Alpha, who turned 13 this year.

One year our school took a field trip from the Chicago suburbs down to the amusement park, Cedar Point in Ohio. Okay, it wasn't "Field trip." The truth of the matter is I was a band nerd, and it was a band competition. Anyway, we stopped and unloaded our buses at a mall, and we were told to go to the food court to get lunch.

I was at the mall with my friends, and from a distance we happened to see two other kids we knew, but never hung out with, clear on the other side of the mall. One of them lived on my street, but he was not someone I hung out with. 

The commotion caught our attention because these two kids were being chased down an escalator by a mall cop. The mall cop was hollering something at them as he was holding up his pants and clumsily clamoring behind them.

While I do not know the full story, the school rumor mill said they got caught shoplifting. I do know they got in trouble and were sent home.

No parent was standing next to us to interpret the moment. I am sure I never went home and told my parents what we saw. My parents, who both read this newsletter, will likely respond saying they’ve never heard that story ;) I’ll report back.

But we learned something. That is what the mall was. It was not just shopping.

It was practice.

You practiced spending money. You practiced making plans. You practiced not being late. You practiced deciding whether to follow your friends or not. You practiced watching someone else make a bad decision and quietly deciding you did not want to be next.

Even something as simple as whether I had to earn the money or my parents gave me $20 for the weekend trip mattered. Maybe it was $40. Whatever the amount, it was finite.

You had to choose. Were you going to forego eating to buy the jumbo stuffed animal and hope to survive off free water fountains? Were you going to eat your friend’s leftovers? Were you going to blow your money early and spend the rest of the afternoon pretending you were not hungry? Were you going to buy the movie ticket and skip the snack?

We did not have mom and dad’s credit card loaded into a phone that we could meaninglessly tap.

We had cold hard cash. We had to keep up with that cash. We had to budget.

That kind of constraint teaches something. It teaches trade-offs. It teaches regret. It teaches generosity when a friend shares fries. It teaches self-control when you have to decide whether the milkshake you want now is worth losing the thing you may want later. I always said yes to the milkshake, and still do.

Constraints form people. Sharing experiences and seeing others succeed or fail shapes us. Charlestowne Mall itself is now part of the story. The City of St. Charles notes that the mall’s interior permanently closed in 2017 after years of tenant loss, with only Von Maur and Classic Cinemas still open with exterior access (City of St. Charles, n.d.). 

That closure was a symptom of a bigger shift. A whole generation did not return to the mall in the same way.

Now, maybe, that is changing.

Here is the leadership takeaway: if you rob a generation of certain childhood experiences, they're going to come to the workplace less prepared.

That sentence may feel blunt, but I think it is true. It’s not meant as an insult. It is meant to make leaders pause and think.

If a young employee did not have as many unstructured social reps, why are we shocked when they struggle in unstructured social environments? If they were not given as much practice navigating awkward moments in person, why are we surprised when awkwardness shows up at work? If they were not trusted to test small boundaries in relatively safe environments, why do we assume they will arrive fully formed in professional ones?

Whether it is the Gen Z stare or just other so-called “awkwardness,” we have to realize something. If you do not have lived experience, you absolutely cannot expect someone to act the same way as someone who did.

No amount of TikTok videos or YouTube gurus can tell you how to be a full-functioning adult, complete with all the wisdom that comes from lived moments, if you have not lived the experience for yourself.

That does not mean Gen Z gets a pass on maturity. It means leaders need to understand where maturity comes from. It comes from practice.

Leaders need to build real community, mentorship, and informal gathering into work. Not forced fun. Not another mandatory team bonding event with cold pizza and a trust fall. Real community. Real apprenticeship. Real multi-age interaction. Real moments where younger employees can watch older employees navigate tension, disagreement, humor, ambiguity, responsibility, and repair. And guess what? It's going to be messy. It's going to be awkward. It's going to be uncomfortable–just like middle school. But sadly, for many of this younger generation, those experiences were skipped altogether.

We talk about unstructured play and multi-age group play as essential for children because it builds confidence and teaches kids how to interact. Then those kids grow up, arrive in the workplace, and we pretend a Slack onboarding checklist will do the same thing. It will not.

Workplaces need more room for unstructured interactions. More lunches without an agenda. More shadowing. More hallway conversations. More leaders who are willing to explain not only what decision was made, but how they made it. More patience with awkwardness, without lowering the standard.

Gen Z is not going back to the mall because malls were perfect. They are going back because the pendulum is swinging.

After years of digital-first convenience, transactional retail, supervised childhood, pandemic interruption, and connection once removed, the physical world feels newly valuable. Not because it is efficient. Because it is inefficient in all the ways humans need.

You bump into people. You smell things. You waste time. You get bored. You make decisions. You watch someone else make a bad one. You laugh about it years later.

That is what digital life struggles to replicate, no matter how incredible the technology gets. Even if we wear glasses that capture everything from our point of view, even if immersive reality becomes more convincing, even if the screen wraps all the way around us, the countless little details of shared experience are still hard to manufacture.

The smell of Mrs. Fields. Sampling music by putting on the headphones at FYE. The cologne cloud at Hollister making you feel you had been swept away to the California beaches. Finding a coin on the ground and tossing it in the fountain.

And yes, even watching the mall cop on the escalator.

I do have hope that Gen Alpha (currently 1 to 13-years-old)  will be a generation whose parents intentionally design a more analog childhood because they saw what constant connectivity did. 

Maybe not everywhere. Maybe not perfectly. But I think the recalibration has already started.

Gen Z may be showing us the first visible signs.

The most digital generation is reminding us that the physical world still matters. And maybe the mall was never really about shopping. Maybe it was about getting just enough freedom to become a more well-rounded person.