Nina’s cursor is vibrating. It’s a subtle, high-frequency jitter that tells you exactly how many milligrams of cortisol are currently flooding her system. She is sharing her screen in a Zoom call with 7 other people, and the software-a proprietary monster built in 2007-is behaving exactly how it was designed to: like a labyrinth built by someone who hates people. There are five tiny windows stacked like a digital game of Tetris. Two separate approval chains are pending, and a frozen browser tab has turned a routine data entry task into a spectator sport. I can hear the collective, muted breathing of the senior developers. They aren’t being mean, not exactly. They’re just waiting for her to find the ‘hidden’ commit button that only appears if you scroll 87 percent of the way down a specific sidebar.

I’ve spent the last 17 hours thinking about this. I actually fell into a massive Wikipedia rabbit hole last night-starting with ‘Cargo Cult Programming’ and ending somewhere in the history of the 17th-century French tax farming system. It’s a weirdly relevant connection. Back then, the system was so complex that you needed a specialist just to tell you how much you owed, and that specialist’s job only existed because the system was broken. Today, we call those specialists ‘Senior Power Users.’ We treat their ability to navigate garbage software as a badge of honor, rather than a symptom of a systemic failure. We watch Nina struggle and we think, ‘She just needs more training,’ when the truth is the system needs an exorcism.

The Digital Sigh and Institutional Gaslighting

Hugo W.J., a mindfulness instructor I know who has the patience of a tectonic plate, once told me that the greatest source of modern suffering isn’t the work itself, but the ‘digital sigh.’ It’s that half-second of soul-crushing hesitation before you click a button you know might crash the app. Hugo W.J. recently tried to help a non-profit migrate their donor list. He told me he watched a volunteer spend 47 minutes trying to reset a password because the security questions required the user to remember the name of their first grade teacher’s pet. The volunteer felt stupid. Hugo W.J., however, saw it as a spiritual violation. He argues that when we build tools that make people feel incompetent, we are essentially committing a form of institutional gaslighting.

I’ll be honest, I do this too. I catch myself being impatient with people who don’t know the keyboard shortcuts in my favorite text editor. I criticize the software’s UI in public, but then I’ll spend 27 minutes explaining to a junior why ‘you just have to know to click the invisible pixel in the corner’ to make the export work. Why do I do that? Because if the tool becomes easy, my 107 hours of struggle to learn it feel wasted. It’s a hollow way to find value in oneself. We should be designing for the ‘Nina’ in the room, not the veterans who have already had their spirits broken by the legacy code.

When an organization treats confusion as a personal failure, it stops being a place of growth and becomes a place of hazing. You see this in every industry. In medicine, the senior residents expect the interns to suffer because they suffered. In law, the paralegals have to navigate filing systems that look like they were designed by M.C. Escher on a bad day. The newcomer doesn’t expose their own incompetence; they expose the organizational design that the insiders have learned to ignore. They are the ‘canary in the coal mine’ for usability. If Nina is confused, the system is confusing. Period.

Accidental Complexity vs. Essential Function

This reminds me of my deep dive into the ‘Antikythera Mechanism’ last night. It was an incredibly complex ancient Greek device, but it served a very clear, specific purpose. It didn’t have unnecessary friction; its complexity was essential to its function. Our modern software is often the opposite. It is ‘accidental complexity.’ It’s the result of 77 different committees adding 77 different features without ever talking to each other. We then hand this Frankenstein’s monster to a new hire and act surprised when they can’t find the ‘Start’ button.

Hugo W.J. often says that ‘clarity is a form of kindness.’ In the context of building a community or a business, this means removing the barriers to entry that serve no purpose other than ego. This is something that platforms like domino Qiu Qiu seem to understand intuitively. They recognize that the goal isn’t to see how much frustration a user can endure, but to provide a pathway where competence can be built without the unnecessary baggage of gatekeeping. When you lower the friction, you don’t lower the standards; you just increase the speed at which people can reach those standards.

I remember a specific mistake I made early in my career. I was working on a database for a small library. I accidentally deleted 27 entries because the ‘Delete’ button and the ‘Save’ button were the same shade of gray and placed side-by-side. My boss at the time spent 37 minutes lecturing me on ‘attention to detail.’ Not once did he mention that the UI was a disaster. I spent the next month feeling like I was too ‘slow’ for tech. Looking back, I wasn’t slow; I was just the only one who hadn’t yet memorized the trapdoors.

Bug Reports vs. Personal Failure

If we actually cared about efficiency, we would treat every ‘beginner’s question’ as a bug report for the system. Instead of saying ‘it’s in the manual,’ we would ask ‘why isn’t it obvious?’ If we did that, we might actually fix the 7 core bottlenecks that hold most teams back. But that would require the ‘experts’ to give up their status as the only ones who know how to work the ancient machinery. It would require a level of vulnerability that most corporate cultures just aren’t ready for.

A Smoother Path Forward

I’m going to go back to my Wikipedia hole now-I think I left a tab open about ‘Byzantine Bureaucracy’-but I’ll leave you with this. The next time you see someone like Nina struggling to find a button during a screen share, don’t look at her. Look at the button. Ask yourself why it’s hiding. Ask yourself how many hours of human life have been wasted looking for it. And maybe, if you’re feeling brave, stop blaming the person who’s new to the maze and start questioning the person who built it.

We need to stop confusing ‘knowing where the bodies are buried’ with actual expertise. True expertise should be about making the complex feel simple, not about making the simple feel like a secret society. Hugo W.J. would probably say that the highest form of mindfulness in work is to create a path for others that is smoother than the one you had to walk. That’s how a culture actually evolves. Otherwise, we’re just 7 people sitting on a Zoom call, watching a cursor shake, pretending that the silence isn’t a symptom of a very expensive, very digital sickness.

I think I’ve spent at least 127 minutes today just fighting with my own email filters. Maybe I’m the one who needs the mindfulness lesson. Or maybe, just maybe, the filter UI was designed by someone who really, really hates productivity. Either way, Nina, if you’re reading this: it’s not you. It’s the 107 lines of CSS that decided the ‘Submit’ button should be invisible on Tuesdays. It’s the system. It’s always the system.