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The other possibility (which is common in startups) is that often the “right way” is different depending on the scale of the system you need to design for. In cases like this you end up with technical debt a year down the line, but at the time the feature was shipped the engineering decisions made were extremely reasonable.

I’ve seen a few colleagues jump to writing off all technical debt as being inherently bad, but in cases like this it’s a sign of success and something that’s largely impossible to avoid (the EV of building for 10-100x current scale is generally negative, factoring in the risk of the business going bust). There’s a kind of entropy at play here.

Big fan of tidying things up incrementally as you go [1], because it enables teams to at least mitigate this natural degradation over time

[1] https://sophiabits.com/blog/be-a-tidy-kiwi



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