There was only one time, where we had every Friday, time to improve the codebase. 2 months later it became every 2nd Friday, though.
I'm really pissed that technical debt is considered as "Hey the dev guys are complaining again".
That's because it's very untransparent to anyone other than the engineers working on a project.
I've had a limited amount of success by making this more transparent. Signaling every time a feature will take longer because of a piece of technical debt the team wants to fix caused the fix to get priority before implementing the 4th and 5th feature affected.
Don't the bean counters at Ford Motor Company (for example) nark on the assembly line workers and industrial engineers and QA/QC folks have work pile up, broken machines lying around, uncleaned trash?
In your example, the worst-case scenario is that someone could die, and that tends to spur on investors to discover the probity within themselves to spend some money avoiding an expensive lawsuit.
But when the devs are complaining about the old code being terrible and making their lives hard, it never seems to hinder them that much to management. They keep banging out new features and fixing bugs, and nothing bad seems to happen. But the drip-drip-drip of bugs keeps increasing, and the new features take a little longer each time, and nobody dies at least, but the thing becomes a haunted moneypit that nobody wants to touch, and you're stuck with it now unless you rewrite it all at huge expense, etc., etc.
Maybe everyone should just treat a piece of software as they would a life. I bet we've all seen some codebases where if it were a friend, you probably would have staged an intervention by now. Your software baby needs absolute care from the get-go until the very end, or it will get sick and probably die, and most likely in a very prolonged and painful way.
The really cool thing is that eventually you're able to deliver large, complex tasks in very brief times and then spring on the PM/management that you're able to do this _because_ you've been refactoring. That's made a believer out of at least one of my PMs.
Obviously this doesn't work in all circumstances - it's not always feasible to get the really systemic, contagious debt cleaned up as part of feature work, and if the PM catches on then it makes this tactic difficult to continue.
The bigger obstacle I've had, though, is other developers who haven't fully bought into a culture of continuous improvement. Fear of breakages causes refactor paralysis, which makes it easier to break things when working on them, which increases fear, and so forth. I'm not really sure the best way to deal with that aside from adding a bunch of unit tests (which I still sometimes get pushback on)
The pushback I received was that keeping the framework code in Source Control would result in it being caught in the JS build/minification script, as well as my spec files. The individual that pushed back was also concerned about JS exceptions since we were up against a release, which speaks to a need for training about how unit test files work. Ultimately I .gitignored the framework folder but wouldn't budge on leaving the test files in, since .gitignoring unit tests defeats the purpose. Then I learned that the build script wouldn't grab those files anyway. :)
My boss at my last job had the mind set of "refactoring only makes it different, not better". I asked him if I could spend some time refactoring our build system. He said no. I eventually did it anyway a few months later, spotted a bug due to the changes, and all of a sudden, build times were cut in half or in 10 in many instances.
Same story for a pretty nasty hunk of code we had for handling sparse arrays. Asked if I could refactor, got told no, did it anyway a while later, and all of a sudden a problem that had been considered borderline infeasible takes like 1 day of work.
There is always some risk that refactoring makes code not only different, but worse. Corner-cases are often there for a reason, and refactoring sometimes misses them, especially when there isn't complete unit test coverage. Since it's often easier to get the core logic right, this likely leads to issues that are discovered in production.
A good boss knows to get out of the way, clear a path if necessary.
If boss can't trust the minions to do the right thing, someone's got the wrong job.
There are many people who have wrong jobs.
More importantly, there are many people who are good, but not perfect. They do some aspects of their work greatly, other aspect less well. Good boss has some idea about that and is able to work with people who are not super great.
Least not last, even very good people often disagree about many things, including whether refactoring is needed or not or what kind of refactoring to do. Even if boss trusted all and listened all, he would still be told plenty of contradictory opinions.
Of course, this only works well on teams where your PM and eng lead don't have a fundamentally adversarial relationship. I like to think this is most teams but does take some getting used to in terms of eng lead and PM communicating priorities and needs, between product moment and code quality.