Dface's Discussion of "Judging and Fixing Your Own Errors"

Imma write about the collapsed paragraph below:

The paragraph

The second sentence:

Yeah, for the goals of “eat sushi for dinner” or “spend under $10 for dinner”, it’d be easy to judge if I failed or not. It’d be easy to judge if I succeeded.

What does “confidently judge” mean? I can tell without finding an error in my judgement? Like, I don’t see major problems like about the money in my bank, about how to count how much I spend, about what sushi is or not.