S8 E15 Why the Holidays Stir Up So Much in Midlife & How to Cope with Ann Bolinger-McQuade
Wed Nov 26 2025
The holidays have a way of stirring up everything at once — joy, nostalgia, gratitude, and for so many of us in midlife, a deep grief for the people and seasons of life we miss. It’s a complicated blend, and it can feel incredibly lonely… even when you’re surrounded by family and celebration.
That’s one reason this episode feels especially personal to me. I was never someone who believed in signs — until after my father passed. And then… they started showing up. Little moments, small winks from the universe that landed exactly when I needed them most. Now I see them all the time, and the truth is: they’re always there. You just have to be open to noticing them.
My guest today, Ann Bolinger-McQuade, understands this better than anyone. As an author and workshop facilitator, she has dedicated her life to helping people recognize these quiet messages — what she calls personal oracles — especially during times when grief feels heavy. After her own breast cancer diagnosis set off a series of life-changing experiences, Ann began to see the world as alive, supportive and filled with guidance.
Together, we talk about why the holidays feel so emotionally charged in midlife, how to hold both joy and grief without guilt, and simple ways to honor the people we miss. Ann also shares how to notice the meaningful “oracles” that often appear during this heightened season, offering comfort and connection when we least expect it.
A few things we discuss:
• Why mixed emotions during the holidays are completely normal — especially in midlife
• How gratitude and grief can coexist without canceling each other out
• Simple ways to feel connected to loved ones who aren’t physically here
If the holidays feel complicated for you this year, this conversation is a soft place to land — and a reminder that you’re never as alone as you think.
Show Notes:
Website: https://everydayextradimensions.com/
Book: Everyday Oracles: Decoding the Divine Messages That Are All Around Us
Instagram: @everydaypersonaloracles
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The holidays have a way of stirring up everything at once — joy, nostalgia, gratitude, and for so many of us in midlife, a deep grief for the people and seasons of life we miss. It’s a complicated blend, and it can feel incredibly lonely… even when you’re surrounded by family and celebration. That’s one reason this episode feels especially personal to me. I was never someone who believed in signs — until after my father passed. And then… they started showing up. Little moments, small winks from the universe that landed exactly when I needed them most. Now I see them all the time, and the truth is: they’re always there. You just have to be open to noticing them. My guest today, Ann Bolinger-McQuade, understands this better than anyone. As an author and workshop facilitator, she has dedicated her life to helping people recognize these quiet messages — what she calls personal oracles — especially during times when grief feels heavy. After her own breast cancer diagnosis set off a series of life-changing experiences, Ann began to see the world as alive, supportive and filled with guidance. Together, we talk about why the holidays feel so emotionally charged in midlife, how to hold both joy and grief without guilt, and simple ways to honor the people we miss. Ann also shares how to notice the meaningful “oracles” that often appear during this heightened season, offering comfort and connection when we least expect it. A few things we discuss: • Why mixed emotions during the holidays are completely normal — especially in midlife • How gratitude and grief can coexist without canceling each other out • Simple ways to feel connected to loved ones who aren’t physically here If the holidays feel complicated for you this year, this conversation is a soft place to land — and a reminder that you’re never as alone as you think. Show Notes: Website: https://everydayextradimensions.com/ Book: Everyday Oracles: Decoding the Divine Messages That Are All Around Us Instagram: @everydaypersonaloracles