From Print to iPad: Designing a Reading Experience

People need to switch from thinking "dumb user" (very bad) or "I suck at design" (bad) to "yay - I learned something". Adding more people into the testing loop is possibly good for objectivity - but really bad for lengthening the feedback loop and making it much less communicative.

It fits in with your general point that we don't talk enough about failure enough. Failure is normal in the design process. I expect the first few iterations to be complete fk ups in one way or another. That's just the way life is. People are complicated.

Be open about it. Test early and often. Learn and improve.