Click. The button glows a faint, mocking blue for a moment before turning grey. The loading icon, a pixelated sand-timer straight from 1997, begins its lazy rotation. You’ve been at this for 17 minutes. All you want is a round-trip flight to Denver for the quarterly sales meeting. A task that, on any consumer website, would take maybe 47 seconds.
But this isn’t a consumer website. This is the company’s mandatory travel portal, “SynergyBook Pro.” It has the aesthetic of a tax form and the user experience of a low-grade migraine. You try to filter by airline, and the entire page reloads, clearing your dates. You select a flight, and it informs you your choice is “out of compliance” with a policy nobody can find, citing subsection C-17. You lean back, the warmth from the laptop pressing into your legs, and feel that specific, modern exhaustion. The exhaustion of fighting a machine that isn’t broken, but is ruthlessly executing a program of bureaucratic self-preservation. You know how this ends. You’ll give up, book the flight on Kayak in under a minute, and then spend twice as long fabricating an expense report that fits the SynergyBook narrative.
It’s designed for the Director of Finance who needs to generate a 237-page report on travel expenditure, broken down by department and leg of journey. It’s designed for the legal department, which has 7 distinct compliance frameworks that must be satisfied for every single transaction. It’s designed for control, for reporting, for audit trails, for liability reduction. You, the person who just wants to get to Denver without a layover in Anchorage, are not the customer. You are the data-entry point. You are the ghost in the machine.
The Absurdity of “LossGuard 7”
Let me tell you about Nora S. She’s a retail theft prevention specialist for a massive big-box chain. She’s sharp, observant, and has an almost supernatural ability to spot a tell. Her job is to document inventory shrinkage. Last Tuesday, she had to process a simple case: a teenager tried to walk out with a $2.77 bag of sour candies. He was caught, the candy was recovered, and he was sent home with a warning. A simple event.
To log this into their system, “LossGuard 7,” Nora has to navigate 47 mandatory fields. Not optional fields-mandatory. She has to enter the exact time, the weather outside (a dropdown menu with options like “partly cloudy” and “intermittent drizzle”), the estimated age of the perpetrator, the SKU of the recovered item, the aisle number where the event was initiated, and a 300-word minimum narrative report. The software requires her to classify the “intent level” on a scale of 1 to 7. She has to upload a signed witness form, even if she was the only witness, which means she has to print it, sign it herself, scan it, and upload the PDF. The entire process for this non-event, this $2.77 recovery, takes her 27 minutes. The system is a fortress of data, built to withstand a federal audit, but it’s being used to document a kid with a sweet tooth. It is the definition of inhuman. It’s so profoundly, absurdly serious that it circles back around to being hilarious, but in a way that you absolutely cannot laugh about. It reminds me of a funeral I was at recently, where something utterly trivial and out-of-place happened, and I felt that awful bubble of laughter rising in my chest in the middle of a eulogy. That’s what using corporate software feels like. A solemn duty so poorly executed it becomes a dark joke.
$2.77
The Designers as Hostages
I used to be loud about my frustrations. I once wrote a scathing public post about a piece of HR software, calling its design an offense against humanity. A week later, I got a quiet email from a lead engineer who worked on it. He didn’t argue. He just sent me a 77-page PDF. It was the compliance and accessibility mandate from their legal and HR departments. Every convoluted screen, every useless dropdown, every baffling workflow was a direct response to a line item in that document.