This is a classic engineering take on the problem. It changes when you become a CTO. Because now technical debt is your problem and the choice whether to fix it or not is yours to make. The flip side here is that wrong choices (either way) can be expensive and even kill your company.

I've been on both sides. Having to beg a manager to get permission to fix a thing that I thought needed fixing. And now I'm on both sides where as a CTO it's my responsibility to make sure the company delivers working products to customers that are competitive enough that we actually stand a chance to make money. And I build our product too.

Two realities:

1) Broken stuff can actually slow down a lot of critical feature development. My attitude as a CTO is that making hard things easier is when things can move forward the fastest. Unblocking progress by addressing the hardest things is valuable. Not all technical debt is created equally. There's a difference between messing with whatever subjective esthetics I might have and shit getting delayed because technical problems are complicating our lives.

2) We're a small company. And the idiot that caused the technical debt is usually me. That's not because I'm bad at what I do but I simply don't get it right 100% of the time. Any product that survives long enough will have issues. And my company is nearly six years old now. The challenge is not that there are issues but prioritizing and dealing with them in a sane way.

How I deal with this is very simple. I want to work on new stuff that adds value whenever I can. I'm happy when I can do that and it has a high impact. Whenever some technical debt issue is derailing my plans, I get frustrated and annoyed. And then I sit down and analyze what the worst/hardest thing is that is causing that. And then I fix that. It's ultimately my call. But I can't be doing this all the time.

One important CTO level job is to keep the company ready for strategic goals and make sure we are ready for likely future changes. So I look at blocking issues from the point of view of the type of change that they block that I know I will need to do soon. This is hard, nobody will tell me what this is. It's my job to find out and know. But getting this right is the difference between failing or succeeding as a technology company.

Another perspective here is that barring any technical moat, a well funded VC-funded team could probably re-create whatever you do in no time at all. If your tech is blocking you from moving ahead, it can be sobering to consider how long it would take a team unburdened by technical debt to catch up with you and do it better. Because, if the answer is "it wouldn't be that hard" you should probably start thinking about abandoning whatever you are trying to fix and maybe rebuilding it better. Because eventually somebody else might do that and beat you. Sometimes deleting code is better than fixing it.