It's the push and pull of creating anything remarkable.  It's something every entrepreneur, investor, leader, or creator of remarkable things struggles with.  If they don't, they're either lying to you, or to themselves.

Is your Judgement right? Or did you miss something in your blind spot? Was your Judgement right, but you didn't Persist enough.

It's a mind-f*ck struggle.

Judgement is a slippery slope of sunk costs and Persistence is the ability to compartmentalize and endure.

The future is a complex set of probabilities. Unmercifully, the outcomes are binary. And that, generally, is how success is defined.  As my friend Yoda would say: "Do or Do Not, there is no Try".

Judgement can be improved.  Judgement is mostly about developing a deep understanding of the variables and probabilities (developing a superior process) when placing a bet on an outcome.  Every piece of data or feedback along the way can help refine your Judgement. Look past the data point itself and understand why that data point happened, or didn't, as you expected it would.

Persistence on the other hand is different.  I'm not sure how to put a finger on it, but it seems to be more about conviction and commitment in the face of negative data and feedback.  Lack of Persistence results in a bad outcome when the Judgement is sound.  The Judgement was right, but the Persistence wasn't there. The inverse obviously is also true.  See: mind-f*ck above.

There's a clear path to improving Judgement, but I don't know how, or even if, you can systematically improve Persistence.  Maybe it's one of those things that you either have it, or you don't.

"If you don't get what you want, it's a sign either that you did not seriously want it, or that you bargained over the price." - Kipling