A milestone birthday, broken escalators, and why good design is really just about handling failure gracefully
Let me set the scene for you.
It’s my birthday. A beautiful milestone, and you already know — a lady never tells. 😉
I am back in Chicago. MY city. The one that built me. The one with architecture that makes you stop mid-stride on the sidewalk and just look up. The one where the wind is pushy and doesn’t ask permission, where Garrett’s popcorn hits you from half a block away and your feet just start moving toward it like you have no choice whatsoever.
That Chicago. My Chicago.
I had a whole vision. And I need you to know — the vision was good.
No hotel birthday. No rental car. A real, stomping-ground, this-is-my-city Chicago birthday. Blue Line. Red Line. Buses. The efficient, reliable transit system I grew up trusting. Tavern style pizza, square cut — deep dish for another ocassion. Harold’s Chicken. A walk along the lake where the wind cools you off in a way no air conditioning has ever come close, and you remember what it actually feels like to be outside and alive and free.
I was going to move through the city the way the city was designed to be moved through. From the inside. Like I never left. Because honestly? I never really did.
The vision was beautiful.
The vision did not account for the broken escalator. Or the broken elevator. Or the stairs. All three flights of them.
Here’s what actually happened.
I’m on the Blue Line fresh off the plane from O’Hare. Two suitcases. Milestone energy activated. Feeling myself completely. I get to my stop and the escalator — the one that was supposed to exist and do its one job — is out of service. I look for the elevator. Also out of service. What greets me instead is a staircase. Three flights. Just standing there, completely unbothered.
And me. And my bags. And my knees, who had very immediate, very specific, very vocal feedback about all of this.
I carried those bags up every single step.
Somewhere between the first flight and the third, sweating in my good birthday outfit in the city I love, something shifted. I stopped being frustrated and started being fascinated. Because this moment — this exact, sweaty, luggage-hauling moment — is precisely where design either holds up or completely falls apart.
I was the edge case. The person with luggage. The person for whom “just take the stairs” is not a workaround — it’s a design failure made visible and personal and physical.
Except here’s the thing: I am not actually an edge case. How many people travel with bags? How many people have mobility limitations? How many parents are moving through that system with a stroller, a toddler, and a prayer? How many workers are hauling things through stations built for someone with nothing heavier than a laptop bag and fully cooperative knees?
We are not edge cases. We are a whole user base. We just weren’t centered in the design.
And this is where my brain went full product designer on my own birthday — and honestly, I would not have it any other way.
The CTA map shows the elevators. Good instinct! Right idea! But if that elevator has been out of service for three weeks and there’s no signage until you’ve already committed to the platform — that is not a maintenance problem. That is a communication failure. A wayfinding failure. A we designed for the happy path and completely forgot that the happy path breaks failure.
I think about this constantly when I’m building anything now.
What’s the broken escalator moment in this design? Not if something fails — when. Because things fail. Servers go down. Connections drop. Users show up with contexts and abilities and situations we never tested for in our perfectly WiFi’d, climate-controlled offices. The question is never whether your system will face stress. The question is what it does when it does.
Does it warn you before you’ve already committed to the wrong path? Does it offer a real alternative or just an apology? Does it treat the person on the broken escalator route like they matter just as much as the person who got the working elevator?
That’s the work. Error messages that actually help you. Offline functionality that doesn’t punish you. Alternative paths that don’t feel like punishment. Systems built for real life — not ideal conditions that only exist in a product brief.
But here’s what I also need to tell you — because milestone birthday stories need the full picture.
I carried those bags. My legs had thoughts. But when I got to the top of that staircase and caught my breath and looked up — that Windy City rush just hit me. Home. All of it, just flooding back. I stood there taking it in, grinning probably, a little sweaty, completely in my feelings.
I felt my Chicago broad shoulders reactivate in real time.
This city taught me a long time ago to keep going when systems fail, when infrastructure disappoints, when your beautiful vision meets a very different reality and you have to improvise your way through. Chicago doesn’t promise easy. It promises strong. And it delivered on that, right there on a platform staircase on my birthday.
I ate at every restaurant on my list. The wind cooled me off like it always has. I was a full blown tourist in my own hometown and I loved every second of it. I rode the CTA and felt the city from the inside and remembered exactly why it will always be home.
And I carried three flights of stairs, but I looked good doing it – or at least tried to hold it together.
Both things are true. Both things matter.
I celebrated a milestone birthday in Chicago and the city gave me exactly the gift I needed — a reminder of what I’m here to do.
Design better stairs. Before someone else has to carry the bags.
That’s the whole job. And I’m just getting started. 🖤
Whitney is a designer who believes the best products are built by people who’ve carried luggage up broken escalators — and came home determined to design better stairs.