The Jefferson Fisher Podcast The Jefferson Fisher Podcast

What to Say When Texts Go Badly

Oct 13, 2026 · 32m

Summary

Jefferson Fisher reviews listener-submitted texts to navigate difficult conversations, starting with a father’s empathetic refusal to let go of a childhood doll and a coworker’s boundary-setting against micromanagement. He analyzes a passive-aggressive boss’s response to PTO and a heated exchange between a mother and son, advising against text-based conflict and suggesting "it sounds like" statements to de-escalate. The episode also covers responding to "why can't you be nice?" by distinguishing kindness from niceness, and handling a friend’s frustration over scheduling conflicts by acknowl…

Topics discussed

Introduction: Navigating difficult texts and emails Case study: Adult child requesting a childhood doll Analysis: Balancing past memories with future relationships Workplace conflict: Coworker reading sent emails and critiquing Boss response: Handling passive-aggressive PTO denial Sponsor break: Athena executive assistant service Family dispute: Mom and son arguing over postcards Rent dispute: Distinguishing between being nice and kind Friendship friction: Managing expectations and apologies
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