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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 (www.jennifer-sanfilippo.com) 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.
View all episodes
By Anne Bonney
4.8
2424 ratings
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 (www.jennifer-sanfilippo.com) 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.