As a therapist, Kylee Shields knows that most cultural models for grief fall short when it comes to the full spectrum of loss we experience in life. She likes the term "ambiguous loss," which was coined by psychologist Pauline Boss in the 1970s to describe losses without clear beginnings or endings—someone physically present but psychologically absent (dementia), or physically absent but psychologically present (missing persons, deployment). There's no funeral, no casseroles, no public acknowledgment, no timeline for when you're supposed to "get over it"—which creates its own special loneliness.

Today, Kylee joins us to explore another type of ambiguous loss: grieving something you never had. As she puts it, "Nobody knows what to do with somebody who has lost the thing they never had." For singles, this might mean mourning the marriage that didn't happen, the children you didn't have, the family story you always pictured. Kylee shares how naming this grief has expanded her empathy and inspired her to create "belonging places" where people can talk about life's "unspeakable" aspects—including through her own podcast, The Belonging Place.

Our conversation ventures into unexpected territory, including what we're calling "ambiguous joy"—those gifts and freedoms that emerge from paths we never chose but rarely get acknowledged or celebrated. Turns out joy, like grief, can be surprisingly complicated to hold.

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