# Finding the Loose Bricks in the Wall: What a Stranded Flight Taught Me About How We Learn *How pushing past the default options helps you find hidden solutions in airlines, technology, and learning* By [Hard Mode First](https://hardmodefirst.xyz) · 2026-07-08 --- Finding the Edges of the System ------------------------------- #### Sometimes you don’t know the true edges of a system until you come up against outlier scenarios. When I accidentally discovered a new way for airlines to help customers who get stranded, it reminded me to why it’s important to spend time pushing the boundaries of any system or tool. Yesterday I was booked on a flight to fly from Dayton, Ohio, to New York City by way of Atlanta, Georgia. But my flight was late. Too late to make my connecting flight. _“Can you book me on a later flight to New York?”_ I asked at the Delta check-in desk in Dayton. _“Looks like all the other flights to Laguardia are sold out,”_ the attendant replied. As a frequent flier, I’m accustomed to the options that airlines can offer when flights are canceled (ie: new flight time, different connecting flight, free night in a hotel), so i started to rattle off other options. _“How about JFK? I’d even do Newark. I just have to get home tonight since the kids are with a sitter.”_ _“Well…”_ the attendant began. _“The only way would be for you to take an Uber to Cincinnati and fly out from there. It’s a 90-min trip, still time for you to catch the 5:30 p.m. flight.”_ I didn’t really want to pay for an impromptu car service, but I had run out of options. My husband was out of town, my kids were stuck with a sitter whose shift ended at 11 p.m. If I didn’t get home tonight, how would the kids get to school? _"Yes,”_ I told him _“Let’s do it.”_ _“Great,”_ the agent replied. _“Rebooking you now.”_ I grimaced as I opened up the Uber app on my phone as I loaded up how much this impromptu 90-min ride would cost. _“And will you be needing ground transportation?”_ _“I’m sorry, what?”_ _“Ground transportation,”_ he repeated. _“Should we book you an Uber?”_ My eyes widened at the thoughts of this novel arrangement: Ground transportation, paid for by the airline service. I shut my own Uber app in a minor triumph. _“Why yes,”_ I said. _“Yes I would.”_ They had me on a pre-paid car out of the airport in seven minutes flat. As we pulled away, I realized I hadn’t just learned a new airline policy. I’d discovered another edge of the system. ![](https://storage.googleapis.com/papyrus_images/e0e8c25f7ec7b90d534be9ae8c7bba3a92c4ee90a295a8585985f871f299e8a7.jpg) Sometimes you think you know a system down cold. Then a new option gets introduced that may surprise you. (image source: Gemini) * * * Why Boundary Pushing is Healthy ------------------------------- #### We tend to assume systems have fewer options than they actually do. Once we’ve learned the “normal” paths, we stop asking what else is possible. But organizations often have strange, little-known accommodations reserved for unusual circumstances. These solutions that only appear when someone pushes beyond the default menu. Yesterday, that edge happened to be a prepaid Uber to another airport. Next time, in some entirely different system, I’ll probably ask one more question before assuming I’ve run out of options. In human-made systems, I’ve got a habit of seeing how far I can push boundaries. Sometimes I hit the edge and I’m snapped back into place. But other times, the bricks in that seemingly sturdy wall are more moveable than they might appear. Finding those loose bricks is a game to me. I like playing it. But there’s more to this than meets the eye. #### **Boundary pushing is a very important step to take when learning _anything_ new.** Kids learn how the world works by pushing the boundaries of what’s considered “socially acceptable” behavior (and subsequently getting called back). Grown-ups learn the rules of systems like airports not by memorizing manuals of every single rule, but by recognizing the patterns of what things tend to happen when flights get canceled or delayed. Oh, and by the way, if you’re learning a new tool or technology, you better believe boundary-pushing is the best way for you do that, too. * * * “It Can’t Do That…” ------------------- #### Over the past year, I’ve helped 2,500+ people build their first AI-powered applications. Suffice it to say, I’ve seen a lot of people learn something new for the very first time. I see how some people approach learning with an open mind, whereas others treat it like taking their vitamins. One thing I notice is that right off the bat? Newbies are very quick to tell me exactly what the AI _doesn’t_ let them do. * _“I can’t integrate with our customized software or tool.”_ * _“It can’t scrape my LinkedIn connections.”_ * _“It doesn’t get the look and feel of this document just right.”_ It’s fine to hit boundaries. It’s important to hit boundaries. The danger is when you misinterpret a boundary as a forgone conclusion of what’s possible: #### _“…and that means I can’t make AI work for me.”_ Every system has walls. Every tool has breaking points. Your first job as a user of the system is to find the edges and then teach yourself how to work within the system. I promise you: **There is another way to do the thing you want to do.** Coming from someone who specializes in teaching people how to learn new things, as a student, I’m a massive pain in the ass. I am incredibly particular about _how_ I learn, about _who_ is doing the teaching, and about _where_ the learning is taking place. I don’t like it when people try to teach me without answering all of my questions, I don’t like it when you tell me the thing (vs. show me the thing), and I certainly don’t like feeling stupid or stuck. I’ve found that this habit of boundary-pushing has served me incredibly well when working with AI tools. And I encourage you to push the boundaries a bit more in your own work too. The next time you meet a new tool or AI model, treat it like you’re meeting a stranger for the first time. First, try asking what it thinks it’s good at, and then throw a few tests its way. See how far you can push it before it outperforms you, before it confuses you, or before you hit a wall. #### When you really think about it, getting stuck in a coding project isn’t really that different from getting stuck in an airport. You may not take a direct flight home, but you can take a connection. You might not arrive the day you wanted, but maybe you’ll get a free hotel out of it. And just when you think you’re out of options, you might discover there’s a free Uber ready to take you to another airport, 90 minutes away. ![](https://storage.googleapis.com/papyrus_images/d2330ac29cf1986ec9c07106da4043b69ed89714d281f80e6a787c57e4434c28.jpg) Don’t let the maze get the best of you. (Image source: Gemini) --- *Originally published on [Hard Mode First](https://hardmodefirst.xyz/finding-the-loose-bricks-in-the-wall-what-a-stranded-flight-taught-me-about-how-we-learn)*