The Cost of Preserving Old Wheels

There’s a pattern I keep running into across the tech stack — from Windows to SharePoint to ConnectWise — and it’s finally time to name it. Not because I’m annoyed (though I am), but because the pattern itself is revealing. It shows how systems age, how companies think, and how architectural decisions echo decades later in places no one expects.

The short version is this:

Some companies preserve the old wheel.
Some companies replace it.
And some keep adding spokes to a wheel that should’ve been retired decades ago.

Microsoft is the canonical example of the first category. Apple is the canonical example of the second. And Canonical is the canonical example of Canonical… I think I’m going off track here. Anyway — the consequences of those two philosophies ripple outward into everything built on top of them.

The Ghosts of 1981

If you want to see what “preserving the old wheel” looks like at the operating‑system level, Windows is the purest specimen.

Windows 11 — a modern OS running on hardware that would look like alien technology to the engineers of the 80s — still cannot create a file named CON or PRN. Not because it’s impossible. Not because it’s conceptually wrong. But because those names were reserved device handles in MS‑DOS, and the path parser still treats them as magic tokens.

Unix solved this in 1970 by making devices files.
Windows never made that leap.

And once you see that pattern, you start seeing it everywhere.

SharePoint Pretending to Be a Filesystem

If Windows shows the pattern at the OS level, SharePoint shows it at the platform level.

SharePoint is a document database from the early 2000s wearing a filesystem costume. Teams and OneDrive are layered on top of it, pretending it’s a folder tree. But it isn’t. It never was. And so the cracks show:

• no symlinks
• no junctions
• no relative paths
• no alias files
• no portable references
• no stable IDs
• no real linking system

Not because it’s impossible — iCloud Drive supports all of this — but because SharePoint’s underlying model was never designed for it. And Microsoft’s culture doesn’t reward breaking old abstractions. It rewards preserving them.

So instead of rebuilding the wheel, they bolt new wheels onto the old axle and hope the illusion holds.

The Drift Toward Polished Turds

And this is where the grotesque little idiom comes in:
you can polish a turd, but it still isn’t gold when you’re done.

It’s crude, but it’s also the most accurate description of what happens when companies keep layering new features on top of old abstractions instead of replacing the abstraction itself.

Windows still forbids filenames like CON and PRN because the path parser is haunted by decisions from 1981. SharePoint still can’t support something as basic as a link because it’s a document database pretending to be a filesystem. ConnectWise still struggles with workflows that feel bolted on because the underlying model was never designed for the way people work today.

These aren’t isolated quirks.
They’re polished turds — legacy constraints buffed to a shine, wrapped in modern UI, and presented as if the underlying structure isn’t quietly rotting.

And users can feel it.
Even if they can’t articulate the architecture, they can sense when a system is fighting itself.

ConnectWise as a Micro‑Microsoft

And this brings us to the business‑workflow level.

This month, a customer left ConnectWise for HubSpot. Not because HubSpot is perfect, but because CW’s architecture is showing the same symptoms as Windows and SharePoint:

• brittle integrations
• inconsistent APIs
• workflows that feel bolted on
• communication channels that leak
• a data model that resists modern expectations

I didn’t “convince” them to leave. I just stopped trying to defend a system that’s failing its own use cases. And the customer followed the gravity.

This is how platforms lose users — not with a dramatic collapse, but with a thousand small decisions where the modern system simply feels less haunted.

The Cultural Divergence

Zoom out far enough, and the pattern becomes cultural.

Apple’s instinct is:

• break the old thing
• rebuild the abstraction
• hide the machinery
• unify the model

Microsoft’s instinct is:

• preserve the old
• layer the new
• expose the machinery
• avoid breaking anything

Neither approach is morally superior. But one of them ages better.

Unix’s simplicity — “everything is a file” — has quietly taken over:

• servers
• networking
• mobile
• cloud
• containers
• DevOps
• AI/ML

Windows is the last fortress. And even Microsoft is slowly retreating into POSIX: WSL, Azure’s Linux backbone, PowerShell Core, .NET on Linux, Kubernetes everywhere.

It’s not collapse.
It’s absorption.

The Drift

What fascinates me isn’t the technical limitation itself. It’s the cultural posture behind it.

Legacy‑preservation cultures eventually lose to abstraction‑driven cultures.
Not because they fail suddenly, but because they calcify slowly.

You see it in Windows’ forbidden filenames.
You see it in SharePoint’s inability to support links.
You see it in ConnectWise losing customers to systems built this decade instead of last century.

And you see it in the quiet, steady rise of Unix everywhere Microsoft isn’t looking.

The wheel keeps turning.
Some companies replace it.
Some companies keep polishing the old one.
And Canonical… well, Canonical just keeps being Canonical.

Drift isn’t decay. It’s the slow accumulation of choices that once made sense.
The trouble starts when we forget to ask whether they still do.

By the way, you can polish a wheel, too.
But if it’s the wrong wheel, all you get is a shinier mistake.
And polished wheels aren’t very grippy anyway.