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Death by Technical Debt
(piefed.social)
A community dedicated to the profession of IT Systems Administration
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They cannot limp along indefinitely, but they can do so for decades. That's exactly the problem. It's a common 'turkey problem'. In my experience, whether the company can get out of the swamp depends mainly on two things: whether bosses/decision makers understand anything at all about technology, and whether they are willing (and, hierarchically speaking, able) to have their skin in the game for big, important changes.
I used to work for a construction company that made hundreds of millions on property management after each build. They were so fine being in their ways, I was laid off after they realized how much work modernization would be.
Fuck 'em. They don't deserve you.