The author reflects on their experience preparing for a TEDx talk during their “Year of Yes.” Initially, they aimed to use the talk to promote their book on transitions. However, after several drafts and meetings with a coach, they realized the original theme wasn’t resonating. The turning point came when the coach encouraged them to share their personal experiences instead. This pivot led to the theme “Let’s Make It Awkward,” which felt authentic and ultimately transformed the talk into something meaningful. The piece explores the idea of pivots in life, contrasting societal teachings about persistence with the potential benefits of letting go. The author highlights examples from Zappos and Amazon, which incentivize employees to leave if they’re not a good fit, suggesting that quitting can be a brave choice. The author argues for more iterative approaches in life, similar to product development, where trying things out before committing can reduce risk and promote growth. They emphasize that pivots can reflect personal growth rather than failure, encouraging readers to embrace change when something isn’t working.