How to Decide If a Hard Conversation Is Worth It

When something feels off in a relationship, how do you know whether to speak up… or let it go?

In this episode of Is It Me or Is It Them?, I walk you through two real-life friendship situations - one that led to a soft, productive conversation, and another that crashed and burned - to help you understand how to make this decision with more clarity and self-assurance.

This episode is especially for you if you tend to overthink conversations, carry resentment quietly, or struggle with knowing when to address something versus adapting your expectations.

In This Episode, We Explore:

• When the hurt or frustration “lingers” and why that’s an important signal
• Why waiting before responding (instead of reacting) can change everything
• What it actually means to “clear the air” — and what you’re really asking for when you do
• A real example of speaking up that led to reassurance, repair, and deeper understanding
• A second example where speaking up led to defensiveness, shutdown, and another problem to be solved.
• How to tell if you’re truly letting something go — or just going quiet and resentful
• Why not every relationship needs the same standards
• How boundaries are often about what you will do differently moving forward
• Letting go of personalization when someone’s behaviour is about their own patterns
• Deciding who still gets a seat at your table — and on what terms
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Mentioned in This Episode: Bold as Love

If this episode resonates, you’ll love the work we’re doing inside The Bold as Love Collective— a small, intimate coaching collective for women who want to:

• stop overfunctioning and overgiving
• navigate hard conversations with steadiness and clarity
• set boundaries without guilt or explosion
• feel more self-trust, confidence, and integrity in their relationships
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👉 Learn more here.

Want to get better at speaking up? Sign up for the free on-demand workshop that will help you be more confident in standing your ground when you're dealing with a boundary bulldozer. Sign up here.

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Please note:

This show is not a replacement for therapy, assessment, treatment or diagnosis. This show is intended for educational and entertainment purposes only. See your physician, counsellor or local crisis support centre if needed

All identifying details about the people and the stories shared here are removed to protect confidentiality.