The Life Coach School Podcast · Brooke Castillo

Ep #513: Types of Regret

February 15, 2024·26 min·2 clips

A student's financial investments failed, leaving her frozen in fear and feeling she let her family down.

Brooke Castillo opens after a weekend with her girlfriend Christine in Miami, describing pickleball, beach time, and watching the Super Bowl. She transitions to a coaching session with a student paralyzed by regret over financial investments that had not worked out, who was blaming herself for affecting family members financially. Castillo describes the pattern she coaches people through: regret as a form of useless rumination that freezes decision-making rather than improving it. She distinguishes regret of commission -- regret for having done something -- from regret of omission -- regret for not having done something. She argues the second type is systematically underweighted in decision-making because it is invisible in advance: people assess the risk of acting but rarely assess the cost of not acting, the missed opportunity, the unlived version of their life. She shares her own condo purchase in Miami as an example of regret of commission: the contract she signed but did not read thoroughly required her to close on the property and then wait 30 days before moving in, meaning she paid costs for a month while unable to occupy the space. She felt frustrated by the developer's expectations but ultimately looked at the contract and confirmed it was written exactly that way. She uses this to model how to process regret: examine what happened, learn from it, and refuse to self-flagellate over a decision that cannot be changed. The broader coaching philosophy is that all events are 50-50 neutral -- neither purely wrong nor right decisions -- and that everything is a series of lessons and corrections toward the life one is meant to live. The episode emphasizes emotional neutrality in retrospective evaluation rather than avoidance of regret entirely.

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