Befriending Grief: How Jill Terwilliger Helps Us Find Meaning in Life’s Most Difficult Transitions
🎧 Listen to the full episode: Episode 59 – Jill Terwilliger: The Many Ways to Grieve and Grow
🔗 Learn more about Jill’s work at AnbauCoaching.com
Inspired by Episode 59 of the Women in… Podcast
Grief is often seen as something to "get over"—a painful chapter we hope to close. But for Jill Terwilliger, an independent grief and change coach, grief is not a linear journey with a finish line. It’s a relationship. In Episode 59 of the Women in… podcast, Jill invites us into a radically compassionate and honest conversation about what it really means to live with grief—and why we might want to stop resisting it and start befriending it.
A counselor with decades of experience, Jill brings a layered perspective to her work. Through her coaching practice at Anbau Coaching and her role as a hospice grief support counselor, she supports individuals and groups facing all kinds of loss—not just death, but divorce, job changes, identity shifts, and more. Her 2024 TEDx talk, Befriending Grief, draws on this deep well of experience and offers a compelling invitation: to tend to our grief the way we would tend to a garden or a wound—with presence, care, and no expectation of a “quick fix.”
What Does It Mean to Befriend Grief?
To “befriend” grief is not to enjoy it. It’s to acknowledge its place in your life, to sit with it rather than run from it. Jill uses the metaphor of tending and befriending—language that softens our cultural instinct to either “fight” grief or “fix” it. Tending grief means creating space for it: giving ourselves time to feel, to reflect, and to honor what was lost. It might look like journaling, ritual, talking to a trusted friend or therapist, or simply allowing ourselves to cry.
Befriending, on the other hand, speaks to relationships. As Jill describes, “When we befriend grief, we stop treating it like an enemy. We learn its language. We let it teach us.”
That teaching often leads to unexpected places. Jill shares that some of the most meaningful moments in her own life—and in the lives of her clients—come through grief, not around it. It’s in the heartache that we reconnect with what matters most: love, legacy, and the bonds we share.
Grief Has No Timeline
One of the most liberating truths Jill shares is that grief has no expiration date. Whether the loss occurred last week or two decades ago, its waves can still rise. Our culture often rushes people to “move on,” but Jill urges us to resist the urge to measure progress by how quickly the pain fades. In fact, the pain may never fully disappear—and that’s okay.
“Grief doesn’t follow a five-step checklist,” Jill says. “It loops, spirals, hides, and reappears when we least expect it. That doesn’t mean we’re broken. It means we’re human.”
This timelessness is especially true when the loss is profound. A child, a partner, a parent—we don't ever really “get over” those losses. Instead, we integrate them into the fabric of who we are. And that takes as long as it takes.
The Spectrum of Grief: Not All Losses Are the Same
In the episode, Jill also touches on an important but often overlooked truth: not all grief is the same. The depth, duration, and expression of grief vary depending on the nature of the loss and the relationship involved.
For example, the death of a grandparent—while deeply sad—might come at the end of a full life, and with some emotional preparedness. The grief may be tender, but it often carries elements of celebration and closure.
Contrast that with the loss of a child, which can feel like the tearing away of the future itself. It’s a kind of grief that defies the natural order and can leave an ache that never truly heals. Jill honors these distinctions without placing grief on a hierarchy. “All grief is valid,” she reminds us. “But it’s also deeply personal.”
There’s also what Jill calls “non-death grief”: the quiet losses that society doesn’t always recognize. Moving to a new city, losing a sense of identity after retirement, ending a long friendship, or watching a loved one slowly change due to dementia—these moments carry grief, too. And they deserve to be named.
Turning Toward, Not Away
Ultimately, Jill's approach is about turning toward our grief instead of away from it. This might feel counterintuitive in a world that prizes speed, productivity, and emotional “resilience.” But Jill offers a different kind of strength: the courage to sit in discomfort, the willingness to feel, and the grace to let healing unfold in its own time.
Her own journey with grief began early, with the loss of her father at 19—a moment that shaped her path forward as a grief educator, hospice chaplain, restorative justice facilitator, and now coach. Each role has added depth to her understanding that grief is not a detour from life—it’s part of the road.
As Jill shares in the podcast, “Grief opens us. It reminds us how deeply we loved, how connected we are. And in that opening, there’s a kind of beauty. A kind of joy we wouldn’t have known otherwise.”
If you’re in the midst of loss or walking beside someone who is, this episode is a powerful reminder that grief doesn’t need to be rushed, solved, or silenced. It needs to be witnessed. And sometimes, simply being present is the most loving thing we can do.
