On a wing and a prayer Definition 1 of 2Pro Tip 1/3Optimistic Undertone Implies hopefulness despite acknowledging risks or difficulties. He started his business on a wing and a prayer, believing in his vision. Pro Tip 2/3Facing Challenges Often used when someone faces obstacles but still pushes forward. She started the race with an injury, running on a wing and a prayer. Pro Tip 3/3Less Formal Suitable for casual conversations rather than formal writing or speeches. I'm just gonna wing it with the repairs and hope for the best.