"I've been able to do things that allow me to hold my head up and still be popular"

This quote by Sam Waterston seems to suggest that the speaker has had the ability to accomplish things that have actually made them respect and affection, while still preserving their popularity among others. It suggests that many times, individuals may compromise their worths or beliefs in order to suit or get acceptance from others, however the speaker has discovered a way to remain true to themselves and still be well-liked. This could be analyzed as a statement about the importance of staying real to oneself and not compromising values in order to acquire appeal or social status.