You Need to Disappoint More People

Key wellness / self-care / productivity takeaways

• Reframe what “disappointing people” means

  • Disappointment is a feeling tied to not meeting someone’s expectations.
  • The goal isn’t avoiding “the no”—it’s handling the internal discomfort that comes after you say no.
  • You don’t need to be “the main character” in how others react; their disappointment is not your responsibility.

• Mindset rule: separate your feelings from theirs

  • Use a “bright line” to remember:
    • My feelings are mine
    • Their feelings belong to them
  • Don’t take ownership of resolving their disappointment.

• Don’t manage their emotions—manage your response

  • After you decline, allow silence instead of over-explaining, negotiating, or trying to soften the blow by fixing it for them.
  • Let them sit with disappointment and process it themselves.

• Validate without rescuing

  • If they react emotionally, validate their experience without trying to remove the discomfort:
    • e.g., “I know this is disappointing. I understand.”

• Build the “disappointment muscle” with small reps

  • Practice saying no to small, low-stakes situations to get comfortable with the feeling:
    • barista/waitress requests (“No, thank you”)
    • street/petition asks (“Listen for a moment, then decline”)
    • minor invitations

• Productivity/leadership communication: start with the no

  • Give clear, confident declines so people can move forward:
    • Start with: “I can’t…”
    • Then add: gratitude (“Thank you for including me”)
    • Then add kindness/closure (“I hope it goes well”)

• Use specific phrase templates

  • “I know this is disappointing. I can’t make it.”
  • “I know this is probably going to disappoint you. I can’t make it.”
  • “I’ve thought about it and I need to say no.”
  • “Not in the cards for me right now.”
  • “I appreciate that, but not in the cards for me right now.”
  • “I need to stop you there. I need to decline.”
  • Dad-style boundary: “You don’t have to like it—you just need to understand it.”

• Avoid toxic over-caring that creates dependency

  • Trying to prevent their disappointment often leads to:
    • stunting their growth
    • keeping them on “training wheels/crutches”
  • Healthy leadership = letting them handle the emotional fallout and build resilience.

• Internal preparation strategy

  • Accept in advance: “They’re going to be disappointed—and that’s okay.”
  • This reduces “parade of terribles” mental spirals before the conversation.

Presenters / sources

• Jefferson Fisher (host / speaker)