Freewheeling/ˌfriːˈwiːlɪŋ/ Definition 1 of 3Pro Tip 1/3Positive Spin Conveys enthusiasm for freedom and spontaneity in actions or lifestyle. His freewheeling spirit inspired others to live more adventurously. Pro Tip 2/3Emotional Connotation Can imply a carefree and joyful attitude toward life. Her freewheeling laughter was infectious. Pro Tip 3/3Context Sensitivity Fits best in casual or creative settings, not formal ones. The team enjoyed a freewheeling brainstorm session.