Podcast Summary: A Place of Yes | A Grief Podcast

Episode: Stepping Away from Work to Make Space for Grief
Host: Heather Straughter (Jake’s Help From Heaven)
Guest: Rebecca Finegloss (Grief Educator, Author, Founder of GrieveLeave)
Date: November 19, 2025

Episode Overview

In this candid and heartfelt conversation, host Heather Straughter welcomes back Rebecca Finegloss, grief educator and founder of GrieveLeave, to discuss the complexities—and necessities—of making space to fully experience grief. The episode explores why taking time for grief and rest often feels impossible in modern life, how workplace cultures can better support grieving employees, what it’s like when your work becomes your grief, and how innovative, community-based events like Sad Hours help break the isolation around loss. Rebecca and Heather share personal stories of loss, “surprise grief,” and the continual balancing act of holding space for sorrow and joy.

Key Discussion Points & Insights

Finding “Yes” Amidst Overwhelm (02:10–05:15)

• Opening Ritual: Both host and guest reflect on recent things they've said “yes” to, underscoring the importance of boundaries.
  • Heather: “Sometimes to protect your yes, you have to say no.” (02:47)
  • Rebecca: Shares about hosting a joyful event for friends during difficult times, leaning into making small, local change as a counter to overwhelm.

The Origin and Purpose of GrieveLeave (05:49–14:11)

• Heather frames the conversation around Rebecca’s pivotal choice after major personal losses: realizing she “could not rest and grieve and work,” and choosing to take time off.
• Rebecca emphasizes privilege in taking a year off and aims to make that learning accessible:
  • “It’s not my recommendation that the average person quit their job for a year… I quit my job so you don’t have to.” (08:12)
• Discusses initial skepticism and concern from others, especially given her background as a high-achieving public sector professional (13:09–16:04).

Public Grieving and Its Social Evolution (16:04–22:18)

• Heather reflects on how her earlier grief journey (after losing her son Jake at 35) lacked community or public discourse about grief.
• Rebecca provides historical insight:
  • “We only shut out grief from public space in the last… 150 years, probably less… It’s so human to grieve.” (18:06)
• Social media and blogs offer a return to public acknowledgment and connection.

Making Space for Grief in Everyday Life (21:53–27:55)

• Practical Ways to Carve Out GrieveLeave: It’s not about lengthy sabbaticals—it can be small, intentional acts:

  • “A grieve leave can look like taking five minutes to listen to your person’s favorite song in the car…” (22:18)
  • Sharing memories at the park, telling stories to children, or simply pausing to reflect.

• The episode critiques linear, transactional cultural models of grieving and sheds light on the need for integrating rather than suppressing loss.

Grieving at Work (26:21–30:13)

• Rebecca challenges the taboo around grieving in professional settings:
  • Suggests putting up a photo of a lost loved one at work, and journaling briefly when grief intrudes.
  • “Your surprise grief is absolutely going to show up at work… Give yourself the space for it.” (31:27)
• Heather notes how workplaces and strangers often avoid mentioning those who are gone.

Balancing Personal Grief and Service (32:21–38:18)

• Discusses the unique challenges faced by grief professionals and empathetic community members who support others through loss.
• Rebecca shares her strategies for replenishment:
  • Purposefully consuming joyful media or pursuing escapist hobbies, e.g., reality TV, shopping (35:53).
  • Setting boundaries at events after being approached for heavy conversations.

The Interplay of Joy and Grief—Surprise Grief and “The Before” (38:18–47:20)

• Both host and guest reflect on how intense, unexpected grief can collide with joyful moments, and reminisce about their pre-loss selves:

  • Rebecca: “Rebecca before… was putting on a performance often because I was so afraid of these really heavy feelings…” (42:13)
  • Heather: Struggles with seeing images of “the Heather before,” yet finds pride now in her resilience and openness.

• They both affirm that holding joy and grief together makes for a richer, more authentic life:

  • “My joy and my grief sit side by side together.” (43:26)
  • “We’re all of it all the time… at different times, what is more forward facing.” (46:49)

Innovative Grief Gatherings: Sad Hours (47:20–53:40)

• Rebecca describes Sad Hours and Meet & Grieve events—casual, secular gatherings for grievers:
  • “I just want to hang out with people who get it… I don’t only want to talk about my dead parents or my grief.” (48:16)
  • Unlike traditional support groups, these are informal and inclusive; conversation can flow naturally between grief and other topics.
  • “There’s a lot of laughter. Hard conversations that make you laugh.” (53:28)

The Future of GrieveLeave & Normalizing Grief in Workplaces (53:40–56:28)

• Rebecca’s upcoming projects:
  • A memoir in progress exploring intersections of marriage, loss, and identity.
  • Expanding Sad Hours, revamping the GrieveLeave website, and growing workplace trainings to make companies more grief-friendly.
  • Speaking at major conferences (EndWell, South by Southwest).
  • Season 2 of her podcast, including an episode on grief and AI.

Notable Quotes & Memorable Moments

• On Boundaries and Finding Yes:

  “Sometimes to protect your yes, you have to say no.”
  — Heather (02:47)

• On Privilege and Taking Leave:

  “It’s not my recommendation that the average person quit their job for a year… I quit my job so you don’t have to.”
  — Rebecca (08:12)

• On The Human Need for Public Grief:

  “It is so human to grieve. So human. And you don’t know that that person in the car next to you is grieving… But you can talk about it on the internet.”
  — Rebecca (19:14)

• On Integrating Grief Into Everyday Life:

  “A grieve leave can look like taking five minutes to listen to your person’s favorite song in the car…”
  — Rebecca (22:18)

• On Surprise Grief at Work:

  “Your surprise grief is absolutely going to show up at work… Give yourself the space for it.”
  — Rebecca (31:27)

• On Joy, Identity and Grief:

  “My joy and my grief sit side by side together. That helps me feel… like the best version of myself that I’ve ever felt.”
  — Rebecca (43:26)

• On Sad Hours Events:

  “The whole concept is just gather people together who want to come to a sad hour because they are self-selecting that they’re grieving in some capacity and they want to just come chill. And like—that is magic.”
  — Rebecca (50:18)

Timestamps for Key Segments

• Introduction and “Place of Yes” question – 00:00–05:15
• Behind GrieveLeave: Rest, Grief, Work – 05:49–14:11
• Public Grieving & Social Connection – 16:04–22:18
• Practical Micro-Grieve Leaves – 21:53–27:55
• Navigating Grief at Work – 26:21–32:21
• Helpers & Burnout: Balancing Service and Self – 32:21–38:18
• Joy, Surprise Grief, and Identity Post-Loss – 38:18–47:20
• Sad Hours & Community Events – 47:20–53:40
• GrieveLeave’s Future, Resources, Events – 53:40–56:28
• Closing Reflections – 56:28–end

Tone & Vibe

The conversation is open, validating, and sometimes darkly humorous. Both speakers share vulnerably—sometimes bringing each other to the verge of (or into) tears—while also making space for laughter and optimism. The episode emphasizes the non-linear, communal, and deeply personal reality of living with grief, and offers both practical strategies and permission for listeners to make room for their own losses.

Takeaways for Listeners

• You don’t have to quit your job to honor your grief; small intentional pauses are powerful.
• Grieving publicly builds connection and reduces shame—isolation is the real enemy.
• Surprise grief is normal, and it often appears at unexpected times, including at work. It’s okay, and important, to make space for it.
• Community events like Sad Hours offer casual, supportive settings that normalize both grief and joy.
• It’s normal for grief to co-exist with happiness; holding both can make you feel more authentically yourself.

Learn more about GrieveLeave and Sad Hours at [GrieveLeave.com]
Listen to Rebecca’s podcast and find grief-informed workplace resources online.