What was the $2,000 rejection challenge Joe Hudson gave his barber?

Joe Hudson told Chris Williamson that his barber painted well but was in no galleries because he feared rejection. Hudson offered him $2,000 if he could collect 50 rejections in the next 60 days. The barber failed to get the rejections because two galleries accepted him, and he now makes a living selling his art and rarely cuts hair. Hudson said the barber was never afraid of making money, only of the feeling of failure, and the challenge reframed each rejection as a win.

• Williamson told a matching story about his business partner selling door to door for npower at one sale in 50 doors, who was told he only needed 98 rejections.

Source: our own transcription of the episode. The full conversation is on Modern Wisdom (2026-11-02). Read the whole episode summary →

▸More from this episode