It takes real confidence and self-awareness to talk to someone who’s considering hiring you and telling them that you aren’t sure you like what you did.

I 100% agree with this sentiment. I've interviewed my share of designers, and one of the questions I often ask when reviewing our design test is "how would you have done this differently, given another go?"

Designers who learn as they create, look at their own work critically, and challenge their assumptions frequently, are often the ones that go far.

This is a good essay. I think some designers I know would humbly admit to doing this all the time. At least for me, my personal ego isn't as interesting as discovering what is really the best solution. It should always be "the best thing," not "the best thing that I made."