The Iconic Midlife with Roxy Manning

Letting Go of the Good Girl: Shame, Self-Compassion, and Midlife Growth with Annalie Howling


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What if the version of you that kept the peace, followed the rules, and carried everyone else… isn’t the version you’re meant to be anymore?

In this powerful and deeply resonant conversation with Unapologetic author, Annalie Howling, we unpack one of the most persistent midlife patterns women struggle to release: the “good girl” narrative — and the shame that comes with outgrowing it.

This episode is about what happens when you evolve in a direction that no longer fits your old roles, relationships, or expectations. When softness is mistaken for weakness. When power feels like a dirty word. And when self-judgment quietly replaces self-trust.

Together, we explore:

  • Why shame is so deeply embedded in how women experience midlife
  • The emotional cost of caretaking everyone except yourself
  • What it really means to outgrow people, identities, and relationships
  • Why softness is not something to fix — it’s a strength
  • How self-compassion becomes the antidote to shame

This is not a conversation about becoming louder, tougher, or more “empowered.”

It’s about becoming clearer, kinder, and more honest with yourself.

If you’ve ever felt pressure to disappear until you’re “better,” smaller, healed, or perfect — this episode is for you.

What We Talk About
  • Letting go of the “good girl / bad girl” binary
  • Shame-based narratives women inherit — and how they show up in midlife
  • Why power doesn’t have to look aggressive to be real
  • The freedom that comes with releasing outdated expectations
  • Self-compassion as a daily practice, not a buzzword

Why This Episode Still Matters

Some conversations don’t expire — they deepen.

This is one of those episodes women return to when they’re navigating growth, transition, or the quiet realization that their life no longer fits the rules they were raised with.

Listen If You’re…
  • Feeling like you’ve outgrown parts of your life but don’t know what comes next
  • Tired of carrying shame that no longer belongs to you
  • Navigating midlife with more honesty — and less performance
  • Ready to trade self-criticism for self-trust

Connect + Continue the Conversation

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The Iconic Midlife is where smart, stylish women over 40 come to reframe midlife on their terms.

New full episodes every Tuesday. Bonus game episodes on Thursdays.

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Social Media: @theiconicmidlife

Host: @redcarpetroxy

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The Iconic Midlife with Roxy ManningBy Roxy Manning

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