The mouse pointer trembles just a little. Sarah is sharing her screen and the cursor is hovering over a button labeled ‘Initiate Stage Four Reconciliation.’ Nobody on the call is breathing. We can all see the seven green checkmarks from the previous stages, mocking us. This is for a $16 coffee receipt.

‘So, once you upload the receipt,’ Sarah says, her voice artificially bright, the kind you use when you know you’re delivering terrible news, ‘it just needs to be validated by your line manager, cross-referenced by finance, audited by procurement, and then it enters the final approval workflow.’

Silence. Utter, dead-air silence on a call with 26 people. This is the sound of collective will being crushed in real-time. This is the dull thud of a thousand tiny inconveniences landing all at once. This new expense system, the one that cost a reported $2,000,006, has successfully transformed a one-minute task into a 16-click procedural nightmare.

The Wrong Question

And everyone on the call is thinking the same thing: Why? Why did we buy a system that makes a simple task five times harder?

I was thinking about this yesterday when a tourist asked me for directions to the train station. I, in a moment of what I thought was cartographic brilliance, sent him on a complex but foolproof route that involved a scenic detour and a clever shortcut through a hotel lobby. He looked at me, utterly bewildered. A woman at the bus stop overheard and said, ‘Or you could just walk straight down this street for two blocks.’ I had solved the problem from my perspective: the most elegant path on a mental map. I didn’t solve his problem: the simplest path from A to B. My solution was for me, not for him.

Your new software is the same. It wasn’t procured to solve your problem of ‘how do I get my $16 back quickly?’ It was procured to solve a manager’s, or a director’s, or a C-suite executive’s problem. That problem isn’t about your convenience. It’s about their visibility. It’s about data. It’s about being able to pull a report at 3 AM that shows departmental spend on caffeinated beverages, broken down by sub-category and correlated with project milestones. Your 16 clicks are the price of that report. You are no longer just an employee; you are a human data-entry node in a vast, glittering machine of managerial oversight. Your inconvenience isn’t a bug. It’s the primary feature.

I have a friend, Marcus M.K., a brilliant food stylist. He makes a tomato look like a work of art. His job is about texture, light, and capturing the essence of ‘freshness’ in a single frame. His firm just spent a fortune on a new digital asset management system called ‘Synertron.’ It promises ‘end-to-end creative workflow integration.’ In practice, it means Marcus now spends 46 minutes after every shoot tagging photos. He has to input the client code, the project ID, the usage rights (internal, external, social), the product type, the color profile, and 26 other mandatory metadata fields for a single JPEG of a sliced tomato. The system can then generate reports on ‘tomato-related asset velocity.’

Marcus told me last week he’s losing his mind. ‘I used to spend my day making food beautiful,’ he said. ‘Now I spend it telling a database what I did.’ The promise was that Synertron would streamline everything. The reality is that the administrative burden was simply shifted from an account manager onto him, the creator. The system didn’t get rid of the work; it just moved it, hid it, and called the change ‘digital transformation.’

The Trap of False Solutions

Here’s the thing, and I know this sounds like a complete reversal: sometimes that visibility is critical. I once worked on a project where a lack of centralized tracking led to a catastrophic budget overrun. Different teams were buying the same assets, ordering duplicate services, with no single source of truth. The final bill was a staggering $236,676 over budget, a mess that took months to untangle. A system that forced every $16 expense through a gauntlet of approvals would have prevented that. So, am I saying this torture-ware is a necessary evil? That we should just accept the 16 clicks and the death of our souls for the greater good of the balance sheet?

Marcus doesn’t need better software to manage his photos of mediocre tomatoes. He needs better tomatoes. When the foundational element is perfect-the perfect color, the perfect ripeness-his job becomes simpler. The lighting is easier. The edits are fewer. The entire workflow shrinks because the quality of the source material does most of the work. You can’t fix a bland, genetically suspect tomato with a $2,000,006 asset management system. You fix it by starting with better genetics. It’s the same reason that expert growers obsess over the quality of their cannabis seeds; they know that no amount of fancy technology or complex process can compensate for a weak foundation. A robust beginning makes the entire journey smoother and the outcome infinitely better.

We keep getting this backward. We’re trying to solve deep, foundational problems-like trust, communication, and process clarity-with a shallow, technological layer. The software is a bandage on a broken bone. It gives the illusion of control while the underlying issue festers.

The True Cost

The real cost of these systems isn’t the $2,000,006 price tag. It’s the slow, grinding erosion of morale. It’s the 46 minutes Marcus will never get back. It’s the collective sigh of 26 people on a Zoom call who just realized their company willingly paid millions to make their jobs just a little bit worse. It’s the death by a thousand clicks, the subtle message that your time is less valuable than a cell in a manager’s spreadsheet.

It’s the conversion of human effort into database entries. And while that might create beautiful reports, it rarely creates beautiful work. The next time you’re stuck on step 11 of 16 for a simple task, remember: the system is working perfectly. It’s just not working for you.