The guest is asked about their favorite failure and how it led them towards success. Focusing on identity crises and a lack of time management, they reveal how certain failures allowed them to embrace where they're now at in their career.
The speaker shares his experience of identity crisis when his plan didn't work out and Jennifer Aniston is asked if she has a favorite failure that made her successful later in life.
The collapse of a 20-year pursuit led to a better life with his family, and the speaker expresses his interest in learning from failures rather than successes.
The speaker reflects on the irony of not always knowing what's best for oneself and how the things one didn't want to do ended up being the best experiences, while the things one wanted didn't always turn out as expected.