I suspect you have no problems making a call on a technical solution that you understand right? Because once you understand the system well enough, the answer i

I suspect you have no problems making a call on a technical solution that you understand right? Because once you understand the system well enough, the answer is obvious such that the question feels like a given. Well obviously you would just... But you can't make a decision here? So the question really is less; How do you know when it's time to walk away. And I assume it's much closer to; How do I decide what I want to optimize for? If you're already completely sure you know exactly what you want to optimize for, then I'm gonna assert you already know the correct decision, and you're either avoiding it because it'll be uncomfortable, or you're already mourning it. As for what to optimize for... I'm one of last people come to for advice... but that's never stopped me from giving it: No one ever wishes they spent more time worrying, no one ever wishes they worked more hours in the office. People do regret throwing more time at something they already thought was a waste of time. (edit: ggoo said this already, and I'm shameful copying the idea from him, because it's too important to ignore. People regret giving up their principles because of some external expectation. Don't forget to consider the things that you consider important for their own worth!)