The Executor Help Podcast

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 young age shaped her perspective, why regrets matter, and how small shifts—not dramatic life overhauls—can help us feel more alive.

A thoughtful conversation about purpose, mortality, grief, relationships, and making the most of the time we have.

For David's book, other resources and more visit www.davidedey.com

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 needed to sign documents.

And what seemed like a simple burial quickly became far more complicated.

In this episode, David speaks with Claudine Lukoweski about the emotional and practical challenges her family faced after her father's passing — and why having conversations and making plans ahead of time matters more than many people realize.

A thoughtful conversation about grief, family communication, burial planning, and the hidden details families often don't discover until it's too late.

For David's book, other resources and more visit www.davidedey.com

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 mug still sitting on the counter to the ordinary objects that suddenly carry deep meaning, this episode explores grief, memory, and the strange stillness of a life paused in place.

A gentle conversation about loss, family, and the ordinary things we often don't notice until they matter most.

For David's book, other resources and more visit www.davidedey.com

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 litigation can take on "a life of its own"
• why families often stop speaking afterward
• and what collaborative law offers as an alternative to court

David also shares personal reflections from his own seven-year family estate battle and the lasting impact it had on relationships.

A thoughtful conversation about conflict, communication, and the hidden cost of fighting over an estate.

For David's book, other resources and more visit www.davidedey.com

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 overwhelming.

A calm reminder that sometimes the hardest part is simply opening the door.

For David's book, other resources and more visit www.davidedey.com

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 people don't always talk about.

Chelsea puts words to emotions many people struggle to explain.

A calm and honest conversation for anyone who has lost a parent—or wants to better understand someone who has.

For David's book, other resources and more visit www.davidedey.com

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.

It's the conversations they didn't have.

This is a simple and honest episode about memory, perspective, and what we carry with us over time.

For David's book, other resources and more visit www.davidedey.com

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.

Daniel shares why this becomes so difficult for families, how emotions often outweigh financial value, and what people can do ahead of time to make things easier.

A practical and eye-opening conversation about what really creates tension—and how to avoid it.

For David's book, other resources and more visit www.davidedey.com

What happens when everything starts falling on you?

In this episode, David talks about the moment many people quietly step into a role they didn't choose.

The one who handles things.

The one others rely on.

The one who keeps everything moving.

At first, it feels like helping. But over time, more and more responsibility starts to land on one person.

David reflects on what that feels like—and the part people don't always see.

A calm and honest conversation about responsibility, pressure, and why carrying everything alone isn't the only way.

For David's book, other resources and more visit www.davidedey.com

In this episode, David speaks with Valerie Oldfield, a death doula who helps families through serious illness, planning, and grief.

They talk about why these conversations feel so hard to start—and what happens when we avoid them.

Valerie shares simple ways to begin. Not in a heavy or overwhelming way, but through small, honest conversations.

She also explains how planning ahead can be one of the most caring things you do for your family.

A calm and practical conversation about fear, preparation, and making things easier for the people you love.

For David's book, other resources and more visit www.davidedey.com