How to Talk About Grief (Without Making It Awkward) with Jennifer Sanfilippo

Grief. Death. Loss. Deep breath. Stay with me. (The name of the podcast should have warned you!) In this episode, I sit down with life transition coach and death doula Jennifer Sanfilippo ( to talk about something we ALL experience… but rarely talk about well. PLOT TWIST: grief isn’t just about death! We explore how unacknowledged losses (like career shifts, identity changes, empty nests, layoffs, divorces and all that) quietly shape our resilience. Because if we don’t learn how to face the small griefs, the big ones hit even harder. We dive into: How to support someone who’s grieving (without saying the wrong thing) Why grief absolutely belongs in workplace conversations How open discussions about death and loss actually build resilience and connection Jennifer also shares her powerful journey from the financial industry to becoming a life transition coach after the loss of her husband, and why creating space for grief is one of the bravest things we can do. Yes, we talk about death, and yes, we laugh because grief and joy can coexist. If you’ve ever felt unsure what to say… avoided the topic… or tried to “stay strong” instead of feeling… this conversation is for you. Chapters 03:08 Understanding Grief and Loss 05:57 The Journey from Finance to Life Coaching 12:03 Building Bridges of Compassion 17:55 Death Cafes: Creating Safe Spaces for Conversation 24:02 Navigating Grief in the Workplace Jennifer Sanfilippo, MBA, is a certified end-of-life doula and executive coach. After her husband Jim died in 2020, she redirected her leadership skills to grief support, facilitating Death Cafés, community forums, and bereavement groups. A mother of two, she lives in Rochester, NY, with three cats and a high-energy dog. Anne Bonney is a keynote speaker and emcee who helps organizations lead through change by building resilience, emotional intelligence, and courageous communication.

You can listen to How to Talk About Grief (Without Making It Awkward) with Jennifer Sanfilippo online on Radio and Podcast. Open the player on this page to stream the available audio.

How to Talk About Grief (Without Making It Awkward) with Jennifer Sanfilippo is an episode from Igniting Courage with Anne Bonney by Anne Bonney.

This episode is 31:31 long.

This episode was published on Mar 9, 2026.

Yes. Use the heart button on the episode page to add it to your favorite episodes list.

Yes. This page shows related episodes from Igniting Courage with Anne Bonney when more episodes are available from the podcast feed.