My thumb is hovering over the ‘ignore’ button, but it’s too late. 5:01 AM. The phone on the nightstand didn’t just ring; it screamed in a pitch that only a wrong number can achieve in the pre-dawn stillness of a generic Marriott. I pick it up, heart hammering against my ribs like a trapped bird, only to hear a man named Kevin ask if ‘Dave’ is ready for the shift. I am not Dave. I am Simon Y., a corporate trainer who has spent 21 years teaching people how to communicate, yet I cannot seem to escape the fundamental breakdown of every system I touch. I told Kevin he had the wrong number, but he argued. He actually argued for 11 seconds that I might be Dave and just forgotten who I was in my sleep. That’s where we are now. The system says I am Dave, so my lived experience of being Simon is secondary.

This morning’s irritation is just the latest entry in what I call the Archive of Failed Transactions. It’s a mental ledger, a thick, invisible binder of every time I’ve handed over my digital currency and received absolutely nothing in return except a ‘processing’ wheel that eventually spins itself into a flatline. We’ve been conditioned to accept these as minor glitches-the digital equivalent of losing a nickel in a vending machine-but when you’re a corporate trainer who lives out of a suitcase 301 days a year, these nickels start to look like a mountain of stolen time and gaslighting.

Take March 2023. I was sitting in an airport lounge in O’Hare, the air smelling of 81-cent industrial carpet cleaner and burnt espresso. I tried to make a Bigo purchase, something small, maybe $51, just to pass the time. The screen flickered. The ‘Success’ message appeared for a fraction of a second, then vanished, replaced by a red ‘Error 401: Connection Timed Out.’ My bank account showed the deduction. The app showed zero credits. I spent the next 41 minutes-I timed it-chatting with a bot that insisted I hadn’t actually pressed the button, despite the fact that my money was already halfway to a server in a different hemisphere.

This is the core frustration of the modern consumer: the normalization of loss. We’ve collectively agreed that if a server blinks at the wrong time, our money simply ceases to exist in a usable form. It enters a state of ‘pending’ purgatory where the burden of proof is shifted entirely onto the victim. I have 111 screenshots on my phone of various ‘Error’ screens. Each one represents a moment where I was told, essentially, that my eyes were lying to me. I’m a professional who teaches ‘Extreme Ownership’ to executives, yet I find myself powerless against a checkout gate that decides to eat my $21 renewal fee and then tell me I’m not a member.

I’ve noticed that the more ‘seamless’ a system claims to be, the more catastrophic the failure is when the seam finally rips. When a physical store clerk overcharges you, you see their face. You see the mistake. You point at the receipt, and they fix it. But in the digital architecture, there is no face. There is only a series of ‘if-then’ statements that never seem to include ‘if the customer paid but got nothing, then give them their damn product.’ Instead, it’s a loop of ‘refer to FAQ’ and ‘check back in 71 hours.’ It’s a design choice. By making the resolution process more expensive in terms of time than the value of the lost transaction, companies effectively profit from their own malfunctions.

I remember one specific instance in June where I was double-charged for a subscription. It was only $11, but it was the principle. I called the support line. I was caller number 151 in the queue. By the time I reached a human, I was so exhausted by the hold music-a MIDI version of ‘Greensleeves’ that felt like it was being played through a wet sock-that I almost apologized to *them* for calling. That’s the psychological trick. They wear you down until the $11 feels like a fair price to pay just to stop talking to them. I hung up, the transaction remained failed in my mind, and the Archive grew another page.

It’s why I’ve become obsessive about where I put my data and my money. I’ve spent 41 minutes explaining to a bot that my coins never arrived. It’s why I finally switched my procurement habits, looking for a

Push Store

that actually registers the handshake between my bank account and the digital server without pretending I don’t exist the moment the ‘pay’ button is clicked. Reliability isn’t just a technical metric; it’s an emotional one. When a transaction works, you don’t think about it. When it fails, you feel a micro-betrayal that stays in the back of your skull, right next to the memory of that 5:01 AM wrong number call.

The Cost of ‘Best Efforts’

I’m sitting here now, looking at the hotel curtains-they’re that heavy, dusty velvet that hasn’t been cleaned since 2001-and I’m thinking about accountability. In my workshops, I tell people that if you say you’re going to do something, the world should be able to set its watch by your word. But the systems we rely on are built on ‘best efforts.’ Your payment went through? Best effort. The delivery was scheduled? Best effort. The refund is coming? Best effort. We are living in a society of ‘best efforts’ while paying for ‘guaranteed results.’

There was a moment about 231 days ago when I actually won. I had a $171 charge for a flight upgrade that never manifested. I didn’t get the seat, but the airline kept the cash. I didn’t send an email. I didn’t use the chat. I wrote a physical letter. A real, paper letter with a stamp-which cost me 61 cents-and mailed it to their corporate headquarters. I think it confused them. No one writes letters anymore. It didn’t fit their automated ‘ignore’ flow. Three weeks later, the money appeared back in my account. But think about the friction required for that. I had to revert to 19th-century technology to solve a 21st-century system error.

We often talk about ‘user error’ as the cause of these problems. ‘You refreshed the page too fast,’ they say. ‘You used an unsupported browser,’ they claim. I’ve been told my internet connection was ‘unstable’ by a support agent while I was literally plugged into a fiber-optic line with 901 Mbps down. It’s a script designed to shift the blame back to the individual. It’s gaslighting as a business model. If they can convince you that it’s your fault, they don’t have to fix the ghost in their own ledger.

I’ve started keeping a physical notebook of these things. It sounds petty, I know. A grown man, 51 years old, writing down every time a digital purchase goes sideways. But there’s power in naming the loss. It stops it from being a vague sense of unease and turns it into data. On page 41 of this notebook, I have a list of ‘Ghost Charges’-money that left my pocket and never reached its destination. It totals $601 over the last year. That’s not a rounding error. That’s a car payment. That’s a weekend away. That’s a significant amount of human labor traded for digital nothingness.

As a corporate trainer, I see this reflected in the workforce too. Employees feel the same way about their ‘internal transactions.’ They put in the effort, they ‘click the button’ on a project, and the feedback loop fails. Their contribution disappears into the system, and no one acknowledges the receipt. We are creating a culture of failed transactions, both financial and interpersonal. We’ve normalized the idea that the ‘send’ button is just a suggestion, not a command.

Maybe the man who called me at 5:01 AM, Kevin, is just another victim of the Archive. Maybe his system told him Dave was in room 401, and he was just following the prompt. He wasn’t trying to wake up a stranger; he was trying to fulfill his own transaction. We’re all just bumping into each other in the dark, guided by algorithms that don’t know our names and ledgers that don’t care about our balance. I eventually fell back asleep for 21 minutes, but the dream I had was just a long line of ‘Loading’ icons dancing across a black screen. When I woke up again, the first thing I did was check my bank app. No new errors today. Not yet. But the day is young, and the system is always hungry for another failed transaction to join the Archive.