Brad Wolfe has spent much of his life asking what gives life meaning. As the grandson of Auschwitz survivors, he grew up hearing stories of unimaginable suffering, survival, and the kind of love that can still exist after profound trauma. Later, when his close friend Sarah was diagnosed with a rare pediatric cancer, Brad found himself showing up at her bedside with the one language he knew best: music. Writing songs for Sarah during her illness became both an offering to her and the beginning of a larger question that would shape his life and work: why wait to live with more love, purpose, and compassion?

In this conversation, Brad and Heather talk about grief, music, post-traumatic growth, and the ways pain can become something meaningful without ever making the loss itself okay. Brad shares the story of his grandparents, the lessons his grandmother left behind, the friendship that inspired his early work with pediatric cancer families, and the creation of Reimagine, a community built around helping people face death and embrace life. They also explore what it means to keep showing up, how small acts of service can carry someone’s memory forward, and why the people we lose can continue shaping how we live. It’s a thoughtful conversation about love, legacy, creativity, and choosing not to wait for some later moment to live more fully.

Resources & Ways to Connect

• Reimagine Website: https://letsreimagine.org/

• Brad Wolfe and the Moon: https://www.bradwolfe.com/

• Jake’s Help from Heaven Website: http://jakeshelpfromheaven.org/

• Jake’s Help from Heaven Instagram: https://www.instagram.com/jakeshelp

• Jake’s Help from Heaven Facebook: https://www.facebook.com/jakeshelp

• APOY Instagram: https://www.instagram.com/aplaceofyespodcast

• Heather’s Instagram: https://www.instagram.com/heathersstraughter

• Our YouTube Channel: https://www.youtube.com/@aplaceofyespodcast

• For more of Heather’s writing and thoughts: https://ohheather.substack.com/

• Everything’s Jakey (Substack): https://everythingsjakey.substack.com/

For most people in Saratoga Springs, Patrick Pipino is known as the guy who always shows up. Whether he's organizing community events, teaching someone how to snowmobile, baking sourdough for friends, or helping a neighbor in need, Pat has built a reputation around generosity and connection. But behind that outward kindness is a loss he has carried for nearly four decades. When Pat was 19 years old, his younger sister Meredith was killed in a tragic house fire set by an arsonist. She was just 13 years old. In an instant, his family was forever changed, leaving behind questions, heartbreak, and a grief that would follow them for the rest of their lives.

In this conversation, Pat and Heather talk about sibling loss, survivor's guilt, and the complicated ways grief evolves over time. Pat shares the lasting impact Meredith's death had on his mother, his brother, and his own understanding of family, as well as the guilt he still wrestles with decades later. They explore what it means to keep someone's memory alive, the challenge of living with unanswered questions, and why small acts of kindness have become such an important part of Pat's life. Along the way, they discuss social media, community, parenting, and the quiet ways the people we love continue shaping who we become long after they're gone. It's an honest conversation about loss, guilt, legacy, and learning to carry grief without letting it define you.

Resources & Ways to Connect

• Jake’s Help from Heaven Website: http://jakeshelpfromheaven.org/

• Jake’s Help from Heaven Instagram: https://www.instagram.com/jakeshelp

• Jake’s Help from Heaven Facebook: https://www.facebook.com/jakeshelp

• APOY Instagram: https://www.instagram.com/aplaceofyespodcast

• Heather’s Instagram: https://www.instagram.com/heathersstraughter

• Our YouTube Channel: https://www.youtube.com/@aplaceofyespodcast

• For more of Heather’s writing and thoughts: https://ohheather.substack.com/

• Everything’s Jakey (Substack): https://everythingsjakey.substack.com/

When Andrea Wilson Woods was 22 years old, she made a life-changing decision: she became the legal guardian of her eight-year-old half-sister, Adrienne. What began as stepping in to provide stability quickly became a true parent-child relationship, with Andrea raising Adrienne through childhood, adolescence, and eventually a devastating liver cancer diagnosis. By the time Adrienne died at just 15 years old, Andrea had spent years fighting for her, advocating for her care, and building a life centered around the person she loved most.

In this conversation, Andrea and Heather talk about the unique grief of losing a sibling who was also your child in every way that mattered. Andrea shares what it was like to navigate the medical system as a young caregiver, the heartbreak of watching friendships disappear after loss, and the struggle of reconciling a life that has been permanently shaped by grief. They also explore intuition, anniversaries, the milestones their loved ones never reached, and the ways we continue carrying someone forward decades after they are gone. Andrea reflects on writing her memoir, Better Off Bald, preserving Adrienne’s own words and artwork, and building a national liver cancer organization in her sister’s honor. It’s a deeply moving conversation about love, advocacy, identity, and what it means to spend a lifetime keeping someone’s memory alive.

Resources & Ways to Connect

• Andrea Wilson Woods Website: https://andreawilsonwoods.com/

• Better Off Bald: https://betteroffbald.com/

• Blue Faery: The Adrienne Wilson Liver Cancer Association: https://bluefaery.org/

• Jake’s Help from Heaven Website: http://jakeshelpfromheaven.org/

• Jake’s Help from Heaven Instagram: https://www.instagram.com/jakeshelp

• Jake’s Help from Heaven Facebook: https://www.facebook.com/jakeshelp

• APOY Instagram: https://www.instagram.com/aplaceofyespodcast

• Heather’s Instagram: https://www.instagram.com/heathersstraughter

• Our YouTube Channel: https://www.youtube.com/@aplaceofyespodcast

• For more of Heather’s writing and thoughts: https://ohheather.substack.com/

• Everything’s Jakey (Substack): https://everythingsjakey.substack.com/

Erica Phelps never imagined she would one day be navigating life after the loss of her daughter, Emmie. Born healthy, Emmie began experiencing infantile spasms as a baby, and over time her condition became increasingly medically complex, requiring around-the-clock care and reshaping every part of family life. In this conversation, Erica shares what it looked like to parent a child with profound medical needs, the identity and purpose that caregiving created for her family, and the devastating reality of losing not only a child, but the entire life built around caring for them.

Erica and Heather talk openly about the rawness of early grief, the physical and emotional weight of losing a medically fragile child, and the complicated process of figuring out who you are after years of 24/7 caregiving. They also explore sibling grief, guilt, honoring a child while continuing to live, and the ways parents try to keep their children’s presence woven into everyday life after they’re gone. Erica shares how donating Emmie’s medical equipment to other medically complex families has become one meaningful way to carry her legacy forward. It’s an incredibly honest conversation about child loss, caregiving, survival, and the deep need to feel understood by people who truly know this kind of pain.

Resources & Ways to Connect

• Jake’s Help from Heaven Website: http://jakeshelpfromheaven.org/

• Jake’s Help from Heaven Instagram: https://www.instagram.com/jakeshelp

• Jake’s Help from Heaven Facebook: https://www.facebook.com/jakeshelp

• APOY Instagram: https://www.instagram.com/aplaceofyespodcast

• Heather’s Instagram: https://www.instagram.com/heathersstraughter

• Our YouTube Channel: https://www.youtube.com/@aplaceofyespodcast

• For more of Heather’s writing and thoughts: https://ohheather.substack.com/

• Everything’s Jakey (Substack): https://everythingsjakey.substack.com/

Kate Walsh grew up alongside the community at Double H Ranch, the camp co-founded by Paul Newman and Charles Wood for children living with serious illnesses. Her connection to the camp began through her father, a pediatric ICU doctor who volunteered there for years and helped shape the experience for countless families. When he was diagnosed with stage four metastatic kidney cancer shortly after Kate’s wedding in 2021, her family was suddenly forced to navigate the impossible balance of celebrating new life while preparing for profound loss.

In this conversation, Kate and Heather talk about caregiving, anticipatory grief, and the way loss reshapes how we move through the world. Kate shares how her family chose to celebrate everything during her father’s illness, why creating moments of joy became so important, and what it looked like to help him spend his final days peacefully at home surrounded by the people he loved most. They also explore parenting after loss, the unexpected moments grief resurfaces, and how carrying someone forward can show up through stories, community, work, and even the smallest everyday interactions. It’s a thoughtful conversation about legacy, family, grief seasons, and learning how to show up better for the people we love.

Resources & Ways to Connect

• Double H Ranch Website: https://www.doublehranch.org/

• Double H Ranch Instagram: https://www.instagram.com/doublehranch/

• Jake’s Help from Heaven Website: http://jakeshelpfromheaven.org/

• Jake’s Help from Heaven Instagram: https://www.instagram.com/jakeshelp

• Jake’s Help from Heaven Facebook: https://www.facebook.com/jakeshelp

• APOY Instagram: https://www.instagram.com/aplaceofyespodcast

• Heather’s Instagram: https://www.instagram.com/heathersstraughter

• Our YouTube Channel: https://www.youtube.com/@aplaceofyespodcast

• For more of Heather’s writing and thoughts: https://ohheather.substack.com/

• Everything’s Jakey (Substack): https://everythingsjakey.substack.com/

Erin Mark has lived with the awareness of death for as long as she can remember. Born with cystic fibrosis and told at just five years old that she likely wouldn’t live past 18, Erin grew up navigating a reality most people never have to face: building a life while believing time may be running out. But instead of letting that diagnosis define her, she spent years determined to squeeze as much joy, laughter, and meaning out of life as possible — even as her health steadily declined and she entered end-stage illness in her 30s.

In this conversation, Erin and Heather talk about what it means to grow up grieving the future you thought you’d have while still learning how to fully live in the present. Erin shares the emotional impact of living with chronic illness, the importance of advocating for yourself when others give up on you, and the perspective shift that comes from surviving beyond the timeline you were once given. They also explore grief that exists beyond death — grieving health, fertility, identity, and the life you imagined for yourself — while holding space for joy at the same time. It’s a powerful conversation about resilience, uncertainty, love, and what can happen when someone refuses to stop fighting for your life.

Resources & Ways to Connect

• Erin Mark Website: https://www.erinmark.com/

• Jake’s Help from Heaven Website: http://jakeshelpfromheaven.org/

• Jake’s Help from Heaven Instagram: https://www.instagram.com/jakeshelp

• Jake’s Help from Heaven Facebook: https://www.facebook.com/jakeshelp

• APOY Instagram: https://www.instagram.com/aplaceofyespodcast

• Heather’s Instagram: https://www.instagram.com/heathersstraughter

• Our YouTube Channel: https://www.youtube.com/@aplaceofyespodcast

• For more of Heather’s writing and thoughts: https://ohheather.substack.com/

• Everything’s Jakey (Substack): https://everythingsjakey.substack.com/

Cassie Wilusz never expected her life to unravel the way it did. What began as a season of happiness — raising her daughter, running a successful café, and rebuilding a close relationship with her father after years apart — was suddenly shattered by a series of unimaginable events. First, her father died unexpectedly in a house fire. Then, just a few years later, her husband Dave was diagnosed with terminal cancer. At the same time, Cassie found herself trapped in a years-long nightmare involving an escalating stalker who terrorized her family while she was already fighting to survive overwhelming grief and trauma.

In this conversation, Cassie and Heather talk about what it means to keep functioning when life becomes almost impossible to carry. Cassie shares the emotional toll of caregiving during Dave’s cancer journey, the fear and helplessness of navigating stalking while trying to protect her daughter, and the frustration of a system that repeatedly failed her. They also explore therapy, resilience, boundaries, and how profound loss can completely reshape the way we value time, relationships, and what truly matters. It’s an intense, honest conversation about survival, advocacy, motherhood, and finding clarity after years spent living in crisis.

Resources & Ways to Connect

• Jake’s Help from Heaven Website: http://jakeshelpfromheaven.org/

• Jake’s Help from Heaven Instagram: https://www.instagram.com/jakeshelp

• Jake’s Help from Heaven Facebook: https://www.facebook.com/jakeshelp

• APOY Instagram: https://www.instagram.com/aplaceofyespodcast

• Heather’s Instagram: https://www.instagram.com/heathersstraughter

• Our YouTube Channel: https://www.youtube.com/@aplaceofyespodcast

• For more of Heather’s writing and thoughts: https://ohheather.substack.com/

• Everything’s Jakey (Substack): https://everythingsjakey.substack.com/

This solo episode from Heather marks what would have been Jake’s 20th birthday—a milestone that brings both reflection and reality into sharper focus. Sixteen birthdays have passed since Jake died at age four, and in this episode, Heather revisits a letter she wrote to him on his first birthday after his death, uncovering how grief has evolved in ways she didn’t fully realize until now.

Heather shares what it means to live with grief over time—the shift from raw fear and constant anxiety to a more familiar, though still painful, presence in daily life. She reflects on the difficulty of imagining who Jake would be today, the weight of unanswered questions, and the quiet moments that still carry him forward. This episode is deeply personal, grounded in honesty, and a reminder that grief doesn’t disappear—it changes, softens, and becomes something we learn to carry.

Resources & Ways to Connect

• Jake’s Help from Heaven Website: http://jakeshelpfromheaven.org/
• Jake’s Help from Heaven Instagram: https://www.instagram.com/jakeshelp
• Jake’s Help from Heaven Facebook: https://www.facebook.com/jakeshelp
• APOY Instagram: https://www.instagram.com/aplaceofyespodcast
• Heather’s Instagram: https://www.instagram.com/heathersstraughter
• Our YouTube Channel: https://www.youtube.com/@aplaceofyespodcast
• Everything’s Jakey (Substack): https://everythingsjakey.substack.com/
• Heather’s Substack (Oh, Heather):⁠ https://ohheather.substack.com/⁠

Shelby Forsythia is a grief coach, founder of Life After Loss Academy, and author of Of Course I’m Here Right Now—a practical, compassionate guide for anyone who wants to better support someone through grief. After losing her mother unexpectedly at 21, Shelby began searching for language that could make grief feel less isolating and more understood.

In this conversation, Shelby and Heather talk about the three core feelings so many grievers carry: feeling crazy, feeling alone, and fearing life will be like this forever. Shelby shares why the words we use matter more than we think, how common comfort phrases often miss the mark, and what actually helps instead. It’s a thoughtful, deeply useful conversation about validation, presence, and the simple language that can help grieving people feel seen rather than shut down.

Resources & Ways to Connect

• Shelby Forsythia Website: https://www.shelbyforsythia.com/

• Jake’s Help from Heaven Website: http://jakeshelpfromheaven.org/

• Jake’s Help from Heaven Instagram: https://www.instagram.com/jakeshelp

• Jake’s Help from Heaven Facebook: https://www.facebook.com/jakeshelp

• APOY Instagram: https://www.instagram.com/aplaceofyespodcast

• Heather’s Instagram: https://www.instagram.com/heathersstraughter

• Our YouTube Channel: https://www.youtube.com/@aplaceofyespodcast

Timothy Schramm has spent more than 40 years walking alongside families in the immediate aftermath of loss. As a funeral director and national spokesperson, he has helped guide thousands of people through grief—often on the worst day of their lives—while also serving as a state and federal mass fatality responder in times of large-scale tragedy.

In this conversation, Tim shares what decades in funeral service have taught him about grief, human connection, and the quiet responsibility of showing up when it matters most. He explains how funeral directors help families make decisions they may not yet understand, why gathering together is such a critical part of the grieving process, and what it means to treat this work as both a calling and an honor. From deeply personal reflections to extraordinary experiences in disaster response, this is a powerful look at the people who help carry others through unimaginable moments—and why those moments shape us forever.

Resources & Ways to Connect

• Tim is a spokesperson for the NFDA. Find out more at nfda.org nfda.organd rememberingalife.com

• Jake’s Help from Heaven Website: http://jakeshelpfromheaven.org/

• Jake’s Help from Heaven Instagram: https://www.instagram.com/jakeshelp

• Jake’s Help from Heaven Facebook: https://www.facebook.com/jakeshelp

• APOY Instagram: https://www.instagram.com/aplaceofyespodcast

• Heather’s Instagram: https://www.instagram.com/heathersstraughter

• Our YouTube Channel: https://www.youtube.com/@aplaceofyespodcast