The Conversations that Matter Most: Estate Planning with Paul Stafford episode artwork

EPISODE · Jun 2, 2026 · 1H

The Conversations that Matter Most: Estate Planning with Paul Stafford

from Messy Middlescence

On a recent walk with a close friend, Tina learned that her friend and her husband had an upcoming appointment to complete their wills. Tina replied how reviewing and updating their wills was something she and her husband wanted to do as well. The friend sheepishly corrected Tina that they were not updating their wills but were actually doing them for the first time. Tina’s friend is in her mid-50’s, highly educated, owns multiple homes and has 3 children in their early 20’s. She explained how they had intended to do their wills since their children were young, but only began the process after pressure from their financial advisor.Tina was surprised they had not drawn up wills before this but only mildly so. By coincidence, Tara and Tina had just finished a conversation a few days earlier with Paul Stafford, a professional estate planner. Tina realized that her friend was the “real-life person” behind the statistics when it comes to estate planning: most of us know this is something we need to do and yet it is so easy to procrastinate and put off doing it.In speaking with Paul, it becomes obvious why this happens. Estate planning is the convergence of 3 topics most people have some difficulties with: money, emotions, and the actual realization that you will die. Still, as Paul states quite clearly, “hope is not a plan”. And everyone – no matter your age, net worth or family– needs some form of an estate plan.The compelling conversation we have with Paul is a little bit practical, a little bit instructional, and extremely motivational. He explains through stories from his own life and decades of professional experiences why it matters to have a say in what happens after you die—and why that clarity is a gift not only to our loved ones but also to yourself. He encourages us to think beyond wills and trusts and ask deeper questions: what has my life meant? What do I hope to pass on? How do I want to care for the people I love after I am gone? What conversations should happen while I still have the chance to have them,Topics discussed in today's episode include:The basic documents every person over 18 should have and the conversations worth having before completing these documents;Why estate planning is not just for wealthy families;What probate is and why many families hope to avoid it;The differences between a will, a revocable (“living”) trust, and an irrevocable trust;Why so many estate plans fail to accomplish what people intended;The reasons to revisit an estate plan created years or even decades ago;How to approach conversations with parents who continue to postpone estate planning;The challenges the digital age creates for families after someone dies;The value of bringing together your accountant, estate planner, financial planner and other advisors;The unique planning considerations that arise when children become legal adults;The deeper questions worth asking: what has my life meant; what do I want to pass on; And how do I want to be remembered.Paul explains that estate planning is ultimately about relationships, legacy and caring for the people we leave behind. The documents matter but they are simply tools that help start important conversations and then hopefully provide guidance to future difficult moments.

Episode metadata supplied by the publisher feed · Published Jun 2, 2026

Embed this episode

Ready to play

The Conversations that Matter Most: Estate Planning with Paul Stafford

0:00 1:00:16

No transcript for this episode yet

We transcribe on demand. Request one and we'll notify you when it's ready — usually under 10 minutes.

No similar episodes found.

Fatherhood Field Notes Ned Schaut Fatherhood Field Notes is where we hear real stories from real men living real lives every week. Fatherhood is not only about being a dad, it incorporates providing and serving a home, loving and serving a spouse, engaging and serving in a community, as well as intentionally serving your children. Fatherhood is an adventure, one full of fun, wild, and messy stories. In this podcast, we will hear stories from real men who have found themselves living the Adventure of Fatherhood. The Craft of Fatherhood episodes are 5-10 minute episodes where your guide Ned Schaut shares stories on his own fatherhood journey. Infinite Loops Jim O'Shaughnessy Every Thursday, join Jim O'Shaughnessy and his favorite people as they arm you with the tools & fresh perspectives required to upgrade your HumanOS and thrive in our messy, probabilistic world.Visit our Substack at newsletter.osv.llc for full transcripts, highlights, weekly doses of timeless wisdom, and a bounty of other goodies designed to make you go, "Hmm that's interesting!" Leah on Love: A Podcast on Dating and Relationships Meleah Manning Each week, Meleah Manning, trauma-informed dating and relationship coach, will bring you all the tools, insights and coaching you need to clear the path to the best relationship of your life.Along with her best kept secrets, Meleah will share interviews with experts and Q&A’s addressing your specific questions.Together, we will dive into the big questions around relationships — including all the messy, sexy, and complicated parts.Whether you’re looking to strengthen the relationship you’re in, heal your heartbreak and choose better partners, develop a stronger sense of self, or move away from dysfunctional patterns into highly functioning ones - this show is for you.Connect with Meleah on Instagram @meleah_manning Starting the Conversation Alice Benham Tune in to hear from Alice Benham - strategist, speaker and best-selling author - as she debunks what it takes to grow, normalises the messy middle and documents her journey with transparency. Come for the actionable insights, stay for the reminder that you're not alone.

Frequently Asked Questions

How long is this episode of Messy Middlescence?

This episode is 1 hour and 0 minutes long.

When was this Messy Middlescence episode published?

This episode was published on June 2, 2026.

Can I download this Messy Middlescence episode?

Yes. Use the download control on the episode player to save the publisher-provided media file.
URL copied to clipboard!