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"The unexamined life is not worth living" - Socrates

I completely agree with this, and so does Stoicism. Writing a journal is an undoubtedly positive step towards eudaemonia, helping you correct past mistakes in the future. However, by constantly seeking to improve yourself, which seems like a good thing (and I believe it is) aren't you are admitting that, currently, you are not good enough? This I believe could then lead to a lack of confidence in one's own abilities. This contradiction seems unnecessary, considering the Stoic would be considered unwavering and most confident in his/her abilities.

So how does the Stoic strike the balance or, just in general, approach this?