If you've ever felt pressure to hold it together after loss, Episode 430 of the Grief and Happiness podcast is for you. Widow, author, and mentor Lisa Woolery shares the unfiltered reality of grief — from bank meltdowns to ill-fated dating attempts — and makes a compelling case for why laughter is one of the most powerful healing tools available. Giving yourself permission to be a hot mess, she says, is the first step toward your comeback.
In This Episode, You Will Learn:
(00:52) From Southern California to Kansas City: the sudden loss that changed everything
(03:42) Why most grief books fall short and what Lisa did differently
(05:11) Writing funny chapters about grief's most painful moments
(07:46) Why laughing without guilt is a powerful grief recovery tool
(10:12) Dating as a widow: sharing her lowest moments so others feel less alone
(13:22) Emily's story: finding love again after swearing she never would
(14:01) The dream that gave Lisa permission to move forward
(16:55) Why widows must stop judging each other's grief journeys
(18:35) What not to say to a widow — and what actually helps
(19:55) You can handle anything, but you don't have to do it all
(22:50) Why Lisa keeps saying yes to new adventures
Lisa Woolery is a widow, author, and widow mentor based in Kansas City, Missouri, raising two teenagers and three dogs after losing her husband Eric suddenly — just eight months after their family relocated from Southern California. A former Vice President of Public Relations at Wells Fargo, Lisa channeled her grief into The Widow's Comeback, an International Impact Award-winning memoir about her first two years of widowhood, alongside a grief calendar workbook, guided journal, and an active Facebook community for widows.
In this episode, Lisa shares why she wrote her memoir with raw honesty and deliberate humor — a direct response to the sugar-coated grief narratives she encountered after Eric's death. From laugh-out-loud chapters about bank meltdowns to candid reflections on the guilt-laden process of dating again, she shows how comedy and self-permission became essential tools in her healing. The conversation closes on Lisa's most powerful takeaway: that she can handle anything, but doesn't have to do everything alone — and that while the \"hot mess\" phase is real, it doesn't last forever.
Connect with Lisa Woolery:
Books: Lisa Woolery - The Widow’s Comeback Series
Let's Connect:
The Grief and Happiness Alliance
Book: Emily Thiroux Threatt - Loving and Living Your Way Through Grief
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