Dear Annie Joy

42: That Was Not the Plan


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When life takes a turn you never asked for, what happens next? In this conversation with Amber Jackson, we talk about grief, growth, and how joy still shows up — even when nothing looks like it was supposed to. If you're holding heartbreak and hope at the same time, this one’s for you.

Amber is a writer, speaker, and fierce believer in honest storytelling. She shares what it looks like to rebuild when the old version of life is gone, how to grieve out loud, and what it really means to hold joy and pain in the same space.

This episode is tender, funny, gritty, and real. It's a true invitation to let go of the plan and lean into what’s actually unfolding.

We talk about:
  • What happens when the life you planned disappears

  • Loud grief vs. quiet grief

  • Rebuilding identity after deep loss

  • Finding joy that doesn’t need permission

  • How true friendship holds space for both the mess and the magic

    Connect with Amber:
    Instagram: @enjoyingholland

    Get her Joy Journal 

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    Dear Annie JoyBy Annie Joy