Sherry argues that "should" is an unhelpful word because it lacks specificity and carries connotations of shame and obligation. When we replace phrases like "I want to" or "I feel like it would be helpful," with “should”, we allow external influences to shape our decision-making instead of relying on our own intrinsic motivation. The word "should" is associated with guilt stemming from societal beliefs that are indirectly imposed and rooted in desires, ethics, and personal growth. Sherry challenges the notion that there is any valid use for the word "should." Drawing from the words of therapists that have come before her, do not “should” yourself and instead advocate for embracing personal choices and inner guidance.
You’ve built something incredible. But when it’s time to sell, are you unknowingly making your exit harder than it needs to be? Most founders...
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Sherry interviews Kim Witczak about the loss of her husband Woody. He was in the early stages of a startup and began to experience...