I was always ashamed of not being able to bang out code without looking at the documentation. One example was file opening/handling in .NET 1.1. I remember not being able to do it even if my life would depend on it. Later on I’ve read that Microsoft made the study about APIs usability. One of the APIs that missed the mark was the IO.
The main complaint was that you need way too many lines of code for basic scenarios.The other complaint was that you need the knowledge of rather abstract (from the usage point of view) inheritance tree. That was a bit of relief. I stopped feeling as such an imposter that was getting payed for doing nothing. Still I regarded this as my flaw and was always irritated when unable to do simple stuff because I forgot API details.
Similarly, after finding out about Ruby I was amazed that alpha geeks figured it out five years before me. When I think about it more carefully, it would not be logical any other way. I speculate that they were able to position Ruby as a Smalltalk derivate that has some Perl syntax sugar and some Lisp functional goodness. That enabled them to label/recognize the whole technology relatively fast and easy.