When you have enough money so you don’t have to work anymore. For most that’s never unfortunately.

Constantly assess the cost and benefit for future scenarios. Give up when the cost goes too high and beats your risk appetite.

In SW development the bar is constantly being set extra high expecting people to meet it constantly if they meet it once. Maybe some random unachievable internal date for some pointless goal for a back slap and a feel good headpat. Yeah, no. You will fail sooner or later as the denizens of management and PM-topia expect that is the norm. Better to relax and let every date be missed and tell them life's a bitch.

I mean this ran straight into Halting problem, and proven impossible to solve.