Oct 6, 2026

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...

Sep 30, 2026

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.

Sep 23, 2026

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...

Sep 16, 2026

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...

Sep 9, 2026

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...