Jonny Lang's song Second Guessing is about a person who constantly doubts their own feelings and instincts. The lyrics describe someone who builds walls around themselves, holding back their emotions and second-guessing their first impressions. They are always rushing in all directions, never stopping to trust their heart or listen to their gut. The song encourages the listener to stop doubting themselves and to trust their emotions and instincts. The chorus emphasizes that you will know when you've found what you're looking for by the way you feel. The lyrics suggest that the person's heart is more trustworthy than their own thoughts that sit in their mind, gathering dust. The song's narrative includes a moment where the person writes down their deepest emotions but then sees their piece of paper fly out the window. They initially feel bad about losing their words, but then imagine a lonely stranger finding them and feel comforted. This moment highlights the theme of letting go and trusting that your words and emotions will find their way to someone who needs them. Overall, Second Guessing tells the story of a person who learns to trust their heart and emotions instead of constantly doubting themselves. The song encourages the listener to stop second-guessing and to follow their intuition.