Flexibility comes from having multiple choices; wisdom comes from having multiple perspectives. Vital for a good leader. It is much less likely for one person to see all the options and to have experienced multiple perspectives.
It’s not only you, external factors also play a role. Many leaders suffer from depression and guilt from perceived mistakes or not planning for each and every bad scenario. I am still learning that life is full of surprises and it is as much about what I expect of the world, as it is what the world offers and expects of me.
Prioritize tech debt as if time and money matters. Each company running IT systems, including the flashy machine learning ones being built today, faces this dilemma at some point in their lifetime. The dilemma is usually: there is nobody left who understands a specific system, or it no longer builds, or making changes takes more and more time, or that one can’t build anything new without spending weeks on various upgrades first.