The thing that frustrates me about developers who feel powerless over technical debt is…who is actually stopping them from dealing with it? They way I see it, as a software engineer, your customer is sales/marketing/product/etc. They don’t care about the details or maintenance, they just want the thing. And that’s okay. But you have to include the cost of managing technical debt into the line items the customer wants. That is, estimate based on doing the right things, not taking shortcuts. Your customer isn’t reading your commits. If they were, they wouldn’t need you.
It would be bizarre if your quote for getting your house siding redone included line items for changing the oil on the work truck, organizing the shop, or training new crew members. But those costs of business are already factored into what you pay at the end of the day.
Yeah management is totally backwards there; it’s like the building manager on a construction project going “all electrical needs to be done in X weeks”, but realistically they have no direct control over that deadline being met by declaring an arbitrary deadline. The unfortunate difference is that if you do a shitty job wiring a building, you’ll fail inspection and have to spend more time and money fixing it. Software can often hobble along; there aren’t strict enforcements for quality that the business can legally ignore, so you’ll always have sad defeated devs go “okay boss, we’ll skip the things we need to get this done faster for you (I hate this job and don’t care about the product’s long term success)”. Having a steady supply of those people will slowly kill a software company.
In the past, I’ve dealt with estimate pushback not by explaining what necessary work can be removed like tests, documentation, or refactoring, but by talking through ways to divide the project more effectively to get more people involved (up to a point, a la mythical man month). That seems to go more proactively. Then we look at nixing optional requirements. But, I’ve also usually dealt with mostly competent engineering management.