According to the Do It Anyway Songfacts there were two inspirations for this song - the birthday cards that Ben Folds mom used to give him and the response from the member of the crowd to how he introduced a ballad he was about to play.
"OKAY! Let's try once again.
Have an unmastered track from the new Ben Folds Five album. It's called "Do It Anyway". The intensity of the track is typical of the rest of the…
You might put your love and trust on the line
It's risky, people love to tear that down, let 'em try
Do it anyway
Risk it anyway