Grief has a way of splitting time. There is the life you lived before the loss, and then there is everything that follows. Somewhere in between, you find yourself asking questions that seem impossible to answer. How do I keep going? Will this pain ever soften? What am I supposed to do with all the love I still have for someone who is no longer here?

My guest on this episode of Crying Out Loud is Rabbi Steve Leder, one of America’s most respected rabbis and the bestselling author of The Beauty of What Remains. For decades, he has walked alongside thousands of individuals and families through death, illness, heartbreak, and unimaginable loss. Yet some of his deepest insights about grief didn’t come from his years in the rabbinate. They came after the death of his own father, when he discovered that some of what he had believed and even taught about grief no longer felt true.

In this deeply moving conversation, Rabbi Leder shares what his own loss taught him about love, faith, regret, anger, forgiveness, and the ways grief continues to reshape us long after everyone else believes we should have moved on. We talk about why healing isn’t measured by how much less something hurts, why grief arrives in waves we cannot control, and why learning to float may be one of the most important lessons any of us will ever learn.

What stayed with me most was Rabbi Leder’s willingness to revisit beliefs he had held for years and admit where experience transformed his understanding. One small change in the way he now speaks to grieving families carries enormous wisdom, and I have thought about it ever since we recorded this conversation.

If you’ve ever wondered whether life can hold both heartbreak and hope, or how love continues after loss changes form, I think this episode will stay with you long after it ends.

In this conversation, we discuss:

• Why Rabbi Steve Leder says he misunderstood grief until his own father died.

• The surprising reason healing isn’t about hurting less.

• What grief and ocean waves have in common, and how learning to float can change everything.

• Why is anger after loss often protecting a deeper emotion.

• The regrets people carry at the end of life, and what they can teach us now.

• How faith changes when tragedy shatters what you thought you believed.

• The one-sentence Rabbi Leder no longer says to grieving families, and what he says instead.

• Why accepting help can be one of the hardest parts of grief.

• What forgiveness really asks of us after profound loss.

• The hidden meaning behind “the valley of the shadow of death.”

• How heartbreak can deepen our capacity for connection, compassion, and joy.

To learn more about Rabbi Steve Leder, follow him on Instagram where he shares a weekly sixty-second reflection, and explore his book, The Beauty of What Remains.

And if you’re moving through grief, heartbreak, or a season of profound change, you don’t have to carry it alone. The Grief Healing Collective offers support, connection, and a community that understands what it means to rebuild a life after loss.

If this conversation moved you, reach out at cryingoutloudpod@gmail.com. Because healing doesn’t happen in isolation, it happens in moments like this one.