Ownership Economics

The Near-Fit Tax

What almost-fitting software actually costs and why the bill never gets challenged.

· 10 June 2026 · 5 min read

It rarely looks like a software problem. It looks like a sales team contorting its pipeline into a CRM’s objects. A marketing team running one campaign across five subscriptions and three automation glues. A finance team that closes the month from a spreadsheet only one person fully understands, because it is the spreadsheet that reconciles what two systems each insist is true.

None of that shows up as a line item. So nobody challenges it. That is the near-fit tax: the recurring cost of running your business on software that almost fits.

Where the tax hides

It hides in four places and you are almost certainly paying in all four.

It hides in hours: the manual re-entry, the export-import-reconcile ritual, the status meeting that exists only because two tools don’t talk. It hides in errors: the wrong field, the double-booking, the number that was right in one system and stale in another. It hides in workarounds: the spreadsheet layer, the shared inbox standing in for a workflow, the “just ping me and I’ll update it manually.” And it hides in licence fees for capability you bought to get the one feature you actually needed.

Each is small. That is the point. A tax you would revolt against as a single bill, you will pay without comment as a hundred small frictions.

Why it never gets challenged

A renewal invoice gets scrutinised. A finance director will negotiate a 12% increase line by line. But the 1.5 people whose real job is bridging two systems? They sit in the org chart as “operations.” The four hours a week your best account manager spends fighting the CRM? That is just “admin.” The tax is distributed across people and weeks until no single instance is worth raising.

There is a quieter reason too. The workarounds are evidence of competence. The person who built the spreadsheet that holds it all together is, correctly, proud of it. Nobody wants to hear that their heroics are a symptom.

How to put a number on it

You don’t need a consultant to find the tax. You need one honest week.

Pick a core workflow: order to cash, lead to close, hire to onboard. Walk it end to end and mark every point where a human moves data between systems, checks one tool against another or maintains a file that exists only because the software doesn’t. Count the minutes. Multiply by the people and the weeks. Add the licences you keep alive for a fraction of their features.

The number is usually larger than the software budget it is hiding behind. That is the finding that changes the conversation, because now the tax has a figure next to it and a figure can be compared against the cost of not paying it.

Most pieces fit. The few that don't become a permanent cost: the near-fit tax.

The disease and the cure

The near-fit tax is the same at every scale. A two-person team feels it as lost evenings. A mid-market operation feels it as a department that shouldn’t need to exist. An enterprise feels it as a seven-figure customisation quote that still won’t quite fit. The disease is identical: process bending to software. So is the cure: software shaped to the process, owned outright, with no licence tax and no workaround layer.

Start with the audit. You can’t decide whether a tax is worth paying until you have seen the bill.

If that week of counting turns up a number you would rather not keep paying, a two-week Fit Assessment puts a defensible figure on it and tells you whether to stay, extend or build.


If this essay names a problem you have, a two-week Fit Assessment puts numbers on it.

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