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Should I Stay or Should I Leave? episode artwork

Oct 15, 2026 9 min

Should I Stay or Should I Leave?

from Stuck is Where it Starts

Should I Stay or Should I Leave? You've been talking about leaving for months, maybe longer. On paper, staying makes sense: the salary, the security, the familiarity, the people you like working with. And yet something keeps telling you it doesn't fit any more. You can't quite name it, and you can't argue yourself out of it either. In Episode 1 I promised to come back to this question, because it's one I'm asked more than almost any other in my coaching practice. In this episode I look at why it's so hard to answer, and even harder to act on. Being stuck isn't the same as being unable to make a decision. It happens when the practical side and the feeling side give you different answers, and thinking harder only ever hears the practical side. In this episode Why stuck lasts longer and runs deeper than an ordinary decision How loss aversion quietly tips the scales towards staying Why we're far more likely to regret what we didn't do than what we did A five-minute handwritten journaling practice to give the feeling side a voice, built around these questions: What will I lose by leaving? What am I losing by staying? What would I gain by leaving, and what does that word actually mean to me? Looking one to three years ahead, which loss would I regret most, and which could I make peace with? If this sounds like someone you know that could find it helpful, please do share it. Thank you! Anne

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This episode was published on October 15, 2026.

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