The blue light from the MacBook is doing something violent to Priya’s retinas at 11:43 p.m. It is a specific kind of late-night exhaustion, the kind where you pretend to be asleep when your partner walks into the room just to avoid explaining why you are still staring at Column AH of a spreadsheet titled FINAL_v9_REALLYFINAL_RECONCILED. This file, currently 103 rows deep and spanning 23 tabs, is the actual heartbeat of a three-generation legacy. It is also, objectively, a catastrophe waiting to happen. To her left is a 43-page PDF from a law firm in London that cost $7,333 to produce and yet contains zero information about which signature is actually missing for the Singapore holding company’s bank account. To her right is a WhatsApp thread from her brother, a string of voice notes and emojis that constitute the only record of a verbal agreement made over gin and tonics in 2023.

The Madness of Shadow Systems

There is a peculiar madness in how we manage complexity. We have these billion-dollar institutions-banks, trust companies, law firms-that operate on the assumption that if they provide enough brittle checklists and standardized forms, the human element will simply fall into line. But human judgment doesn’t fit into a PDF form with a fixed character limit. When the official system fails to capture the nuance of a family’s internal logic, the family builds a shadow system. They build an Excel sheet. And in that moment, power shifts. It migrates away from the named trustees and the fancy directors and lands squarely in the lap of whoever knows the password to that one file on a shared Dropbox. Governance ceases to be a matter of law and becomes a matter of folklore. It’s a transition from infrastructure to memory, and memory is a notoriously leaky bucket.

I’ve spent the last three days thinking about how much of our professional lives is spent performing ‘organization’ while actually just managing chaos with better fonts. My friend Jamie C.M., who works as a virtual background designer for high-net-worth individuals, tells me that his entire business is based on this discrepancy. People want to sit in front of a digital library of leather-bound books while they are actually sitting in a room full of unfolded laundry and unfiled tax returns. Jamie C.M. recently designed a background for a client that featured 13 identical Ming vases, but he told me the client couldn’t even find his own birth certificate when it was time to renew a passport. We are obsessed with the facade. We love the idea of the ‘Trust,’ the ‘Holding Company,’ and the ‘Structure,’ but we ignore the plumbing. And the plumbing is always an Excel sheet maintained by someone who is too tired to be doing it at 11:43 p.m.

The Paradox of Control

I hate spreadsheets. I really do. They are the duct tape of the financial world-necessary, sticky, and eventually prone to drying out and letting everything fall apart. Yet, here I am, opening a new tab to track my own 23 minor commitments for the month. It’s a contradiction I can’t quite shake. We criticize the tools that keep us enslaved to the manual grind, yet we refuse to let go of the control they provide. Because if we move to a transparent, automated system, we lose the ‘magic’ of being the only person who knows where the bodies are buried. There is a strange ego in being the File Keeper. If Priya deletes her spreadsheet, the family’s understanding of their own wealth vanishes. That is a terrifying amount of power for a single file to hold, and yet we see it in 83 percent of the families we talk to.

When we talk about the failure of institutions, we usually talk about corruption or incompetence. But the more common failure is translation. An institution takes a human desire-‘I want to make sure my grandchildren can afford university without becoming lazy’-and translates it into a 53-page legal document that mentions 3 different jurisdictions and a tax code from 1983. The human element is lost in translation. So the family, feeling the disconnect, creates the spreadsheet to translate it back into something they understand. ‘Tab 3: Education Fund.’ Now they have two systems. One is legal but incomprehensible; the other is comprehensible but has no legal standing. This is where the friction lives. This is where the $233 late fees come from, and where the family arguments that last 13 years begin.

Stripping Away the Folklore

It’s not just about the data. It’s about the emotional weight of the data. Every cell in Priya’s sheet represents a conversation, a compromise, or a secret. There is a row for the aunt who doesn’t speak to the uncle, and there is a hidden column for the investment that everyone agreed was a mistake but no one wants to admit. When you move this into a real system, like what they do with ADGM foundations, you aren’t just moving numbers. You are attempting to strip away the folklore and replace it with something that survives the death of the person who created the file. It’s a move toward institutional-grade transparency that honors the human intent without being held hostage by the human’s specific Excel habits.

I once tried to help a client who had 43 different entities across 13 countries. He told me he had it all under control. Then he opened his laptop and showed me a folder titled ‘NEW FOLDER (2).’ Inside was a single text file with the login credentials for every single entity. That was his ‘system.’ He was one forgotten password away from a total multi-generational collapse. It’s a miracle we aren’t all in a state of constant panic. We pretend that because we have a fancy office or a high-priced lawyer, we are ‘set up.’ But setup is a verb, not a noun. It’s a constant process of ensuring that the shadow system doesn’t become more important than the actual structure.

The Vulnerability of the Keeper

Jamie C.M. once told me that the most popular background he sells is a minimalist white office with a single succulent. People want to look like they have nothing to hide because their digital lives are actually overflowing with 733 unread emails and 3 different versions of the same trust deed. We are all Priya, in a way. We are all staring at the screen, hoping that if we just get the formatting right on this one sheet, the complexity of our lives will finally make sense. But it won’t. Not until we stop relying on the folklore of the ‘Final_v9’ and start building systems that are actually designed to hold the weight of a legacy. It requires a certain vulnerability to admit that the spreadsheet is a liability. It requires admitting that we might not be the best people to be the sole keepers of the record.

I’m looking at my own screen now. It’s nearly midnight. I should have been asleep 23 minutes ago. I can hear the hum of the refrigerator, a reminder of the mundane world that exists outside of these digital cells. There is a specific kind of peace that comes from realizing that the system you built is too small for the life you are living. It’s a signal to grow. To move away from the manual, the fragile, and the hidden, and toward something that can actually stand on its own. The spreadsheet is a bridge, but you aren’t supposed to live on the bridge. You’re supposed to cross it and get to the other side, where the governance is clear, the data is real, and you don’t have to pretend to be asleep just to avoid talking about Column AH.

The Lasting Structure

What happens when the person who knows where everything is simply stops knowing? What happens when the folklore is forgotten? We build these empires on the assumption of our own permanence, but the only thing that actually lasts is the structure we leave behind. Not the version with the most tabs, but the version that doesn’t need us to explain it.