Hi Nikolaj, thanks for sharing your insights. It's comforting to know that you guys are human too - struggling with imposter syndrome, and second-guessing your choices. This is probably why developers get so good at what they do because they're always looking to improve not just themselves but the product/team/company.
I think a healthy work culture is when management trusts the developers enough to make good decisions, but not to an extent to be so lax on the contribution of technical debt - or to acknowledge it and not have an action plan to deal with it. Also I think good management should value developers who concerned about long-term sustainability of an ageing codebase. These developers have the company's best interests in mind.
If all companies had a Gary, or maybe a little bit nicer, or a Nikolaj, and they became the management, then just maybe there would be even more 10x developers out there because we'd all be taught the right things.