The Executor Help Podcast

Why are we so uncomfortable with grief when every one of us will experience it?   This week, David sits down with grief educator, social worker and author Lisa Keefauver for a candid conversation about what grief really looks like—and why so many of us get it wrong.   Lisa shares what she learned after the death of her husband, Eric, including the things people said that hurt, what actually helped...

What are you saving for later?   The good bottle of wine. The nice restaurant.   The trip you've been talking about.   The golf course you'd love to play.   In this short solo episode, David wonders whether we sometimes get a little too good at waiting.   Planning for tomorrow matters. Getting organized matters.   But that doesn't mean we should keep putting off the things that bring us joy today....

What happens to your digital life when you die?   Your photos. Passwords. Email. Social media. Online accounts. Important documents. Even the information sitting on your phone.   In this episode, David talks with Niki Weiss, founder of Endevo and a digital thanatologist, about a part of estate and legacy planning many families rarely think about.   Niki explains why our digital lives can create an...

Nobody applies to become the Responsible One in a family.   It usually starts with something small. A ride to an appointment. A prescription to pick up. A form Mom doesn't understand.   Then, little by little, everyone starts calling you.   In this short solo episode, David talks about how responsibility quietly accumulates — and why the person everyone depends on can eventually find themselves wo...

When Davis Wilkinson was 14, his older brother Adam died from an overdose.   While grieving the loss of his brother, Davis watched his mother take on another burden few people talk about — the hours of paperwork, phone calls and frustration that begin after someone dies.   One memory stayed with him: listening as his mother struggled simply to cancel Adam's gym membership.   In this episode of The...

Most of life isn't made up of big moments.   It's coffee with Dad. A phone call from Mom. Nine holes of golf with a friend. Sitting around the kitchen table talking about nothing in particular.   In this short solo episode, David reflects on the ordinary moments that often become some of the memories people treasure most after someone is gone.   It isn't about living as though every moment could b...

What does it mean to love someone when you can't fix what they're going through?   Yvonne Heath knows that feeling personally.   Yvonne is a nurse, speaker, author and founder of Love Your Life to Death. In her book Addiction, Grief, and Joy: A Son's Struggle and a Mother's Love, she shares her family's experience of loving her eldest son through addiction.   In this deeply personal conversation,...

"I think they know." Those four words can leave a family with more uncertainty than we realize. In this short solo episode, David talks about the difference between having the paperwork done and making sure your family actually knows what you want . A will and power of attorney may be in place. The important papers may be organized. But families can still be left wondering: What did Mom really wan...

What happens when you can't find the words for what you've been through?   For Liliana Del Vedova, photography became a way to express what words couldn't.   In this episode, David and Liliana talk about grief, trauma, healing, and why people sometimes don't need someone to fix them or tell them how to move forward.   Sometimes they simply need to feel seen.   Liliana shares how her own difficult...

How often do we spend so much time preparing for tomorrow that we forget to enjoy today? If you're the Responsible One in your family, you probably know the feeling. There's always another form to complete, another conversation to have, another task to cross off the list. In this solo episode, David shares the story of a couple who spent months organizing their affairs. When they finally finished,...

  Most of us think we'll have time.   Time for one more visit.   One more conversation.   One more chance to say what matters.   But sometimes life changes without warning.   In this episode, David has a conversation with Elizabeth De Sevo , author of Choose Your MOMents, to talk about the sudden loss of her mother and how that heartbreaking experience completely changed the way she looks at life....

Every family seems to have one.   They're not always the oldest child.   They're not always the executor.   They don't ask for the responsibility.   But when life becomes uncertain, they're the one who quietly steps forward.   In this solo episode, David shares a realization that came to him after several unexpected conversations.   Different people.   Different families.   The same quiet pattern....

In Part 2 of David's conversation with Dr. Robert V. Hurst, author of Life's Fingerprint, they explore why family dynamics become so complicated when parents begin to age, caregiving decisions need to be made, and estates eventually have to be settled.   Why does one sibling become "the responsible one" while another steps back?   Why do conversations about health care, finances, and inheritance s...

Have you ever wondered why the same family arguments keep happening—even decades later?   In Part 1 of this two-part conversation, David sits down with Dr. Robert V. Hurst, author of Life's Fingerprint, to explore how birth order and childhood family dynamics can quietly shape our personalities, relationships, and decision-making throughout our lives.   Why does one sibling naturally take charge w...

There's a sentence that doesn't often get said out loud, but it sits underneath many of the conversations families avoid: "I don't want this to be hard for you." In this short reflection, David explores the quiet motivation behind getting organized, having important conversations, and making plans for the future. Because for most people, it's not really about documents, lists, or paperwork. It's a...

In this special Father's Day conversation, David speaks with author and editor Margaret McMullan about her book Every Father's Daughter , a collection of essays from 24 women reflecting on the impact their fathers had on their lives.   Together they explore the unique bond between fathers and daughters, the lessons that stay with them the relationships that shape them, and why the influence of a f...

For this Father's Day special, David reflects on his own relationship with his father and the things that continue to stay with him years later.   He shares the story of a difficult Father's Day that changed his family forever, the moment he had to make a decision no son wants to make, and how his understanding of his father evolved over time.   This is not a story about perfection.   It's a refle...

What if you knew exactly how many Mondays you had left?   In this episode, David speaks with Jodi Wellman, author of You Only Die Once and founder of 4000 Mondays.   Together they explore why so many people drift through life on autopilot, why we avoid thinking about our mortality, and how a simple question can completely change the way we think about time.   Jodi shares how losing her mother at a...

When Claudine's father passed away at nearly 90 years old, the family believed at least one thing had already been figured out — he wanted to be buried with his parents.   But after his death, the family discovered something unexpected.   The cemetery records were wrong.   Ownership of the burial plot wasn't clear.   Old paperwork had to be tracked down from decades earlier.   Multiple siblings ne...

There's a moment many families never think about ahead of time.   Not the funeral.   Not the paperwork.   Not the phone calls.   The first time you open the door.   In this quiet and reflective solo episode, David talks about the emotional experience of walking into someone's home after they've passed away—and why that moment often stays with families long after everything else.   From the coffee...

When families fight over an estate, most people assume the only path forward is court. But what does that process actually do to a family? In this episode, David speaks with Bruce Young, founder of Collective Agreement and a Certified Executor Advisor, about what really happens when estate disputes turn into legal battles. Together they explore: why estate conflicts become so emotional how litigat...

Many people know they should talk with their family about important things. They just don't know how to begin. In this short episode, David talks about why these conversations often feel harder than they need to be—and why most families are not avoiding the conversation as much as they are afraid of starting it the wrong way. He shares three simple ways to begin without making it heavy, formal, or...

What does it really feel like to lose a mother?   In this episode, David speaks with Chelsea Ohlemiller, author of Now That She's Gone.   She shares her personal experience of losing her mother and what grief has actually been like for her.   This is not a conversation about fixing grief or moving on quickly. It's about what the experience really feels like—day to day, over time, and in ways peopl...

Why do some things only become clear later?   In this episode, David shares a personal reflection about his mother.   He talks about the small things that stayed with him. The quiet moments. The way she showed up, and what he understands now that he didn't see at the time.   He also reflects on something he sees often in his work—how, after someone is gone, it's not the paperwork people remember....

Why do families fight over things after someone dies?   In this episode, David speaks with Daniel Glazier , a personal property appraiser who has been in thousands of homes helping families deal with what's left behind.   They talk about a part of estate settlement many people don't expect.   It's not the paperwork.   It's the stuff.   Furniture. Keepsakes. Personal items that carry meaning.   Dan...