Great food for thought in this episode. Frequent quitting disrupts a thread of purpose and focus in any undertaking. If you are not passionate about any undertaking, persistence is difficult, if possible at all.
Two ways to quit (or start) any undertaking are to research before you move, or just leap.
For me it depends on the potential. For example, when launching products, if we have NO users, get it out the door. If we have a 1/2 million users and don't want to bring it to a quarter million users, then we better research our hypothesis before we leap. However, we better not take too long, or we will miss the opportunity window.
I have not even addressed the emotional experience in quitting when you think you should stay and staying when you think you should quit or staying when you think you should stay and you should have really quit vs. the opposite.
One of my favorite quotes from a mathematician is "there are two ways to solve a math problem, brute force or elegance. The problem is we cannot predict when elegance will occur."
To me, this is the elegant statement on quitting. If we think elegance will extend our lifetime, or cost more time than it is worth, then we should quit. Problem is, elegance could be just around the corner.