Jill on Money with Jill Schlesinger

Episode: Estate Planning Awareness

Release Date: October 24, 2025

Overview

In recognition of National Estate Planning Awareness Week, host Jill Schlesinger focuses on one of her favorite financial topics: estate planning. She’s joined by Juliet Caleb, a New York estate planning attorney, and Rick Kaler, a South Dakota-based fee-only financial advisor and financial therapist. Together, they explore the emotional, practical, and behavioral hurdles that prevent people from completing their estate plans—and offer actionable insights to help listeners tackle this task. The discussion leans into why estate planning is often delayed, how family dynamics impact the process, and practical strategies for moving past psychological roadblocks.

Key Discussion Points & Insights

1. Why People Avoid Estate Planning

Timestamp: 03:29 – 04:24

• Fear and Superstition:
  Many people fear that drafting estate documents will hasten their death, a belief more common than many realize.

  • Rick Kaler: "If I actually start drawing the documents, I’ll die." (03:43)
  • Juliet Caleb: "Oh, that’s very common. People are very superstitious. More than you would think." (04:05)

• Normalizing Procrastination:
  It’s common to put off estate planning. Instead of shaming clients for delay, professionals should encourage curiosity about the root of resistance.

  • Rick Kaler: "Normalize it... 68% of people don’t have estate plans or documents. But rather than try to convince them, it’s best to understand why." (03:32)

2. Emotional Barriers and Family Dynamics

Timestamp: 04:24 – 05:44

• Facing Family Issues:
  The process often surfaces complex family dynamics and secrets, such as poor financial habits or the anxiety of discovering a relative’s hidden financial status.

  • Jill Schlesinger: "It really makes you confront certain aspects of your family dynamic... If you find out your parents have been hoarding all this money and you’ve been struggling, what does that bring up to you?" (04:47)

• Value of a Dispassionate Observer:
  Bringing in an estate attorney, financial therapist, or financial planner helps navigate these emotionally charged topics.

  • Jill Schlesinger: "You have someone who is a dispassionate observer... and expert." (05:21)

3. The Difficulty of Completing the Process

Timestamp: 05:44 – 07:03

• Why Estate Plans Stall:
  Clients frequently begin the process but pause at the draft stage, feeling the hardest part is already behind them—when in fact, completion is critical.

  • Juliet Caleb: "By the time they read the drafts... they’ve done so much of the hard work. A lot of people believe, well, I’ve gotten it that far, so I’ve... accomplished a lot, so I can kind of take a break. But at the end of the day, they haven’t really accomplished anything that’s permanent." (06:15)

• Role of Gentle Reminders:
  Kind reminders and encouragement help move clients to completion.

  • Juliet Caleb: "Very kind reminders... and explaining that the worst is over, then they can kind of close the chapter on this for a while." (06:47)

4. Talking to Family About Estate Plans

Timestamp: 07:03 – 08:05

• Should You Tell Your Kids?
  There’s reluctance to discuss estate plans with heirs, especially if children are perceived to be "bad with money."

  • Jill Schlesinger: "Do you bring them in and have this conversation ... or do you let them find out when you die?" (07:14)

• The Value of Guided Conversations:
  Most people avoid the conversation, but having a neutral third party can help create agreement and clarity.

  • Rick Kaler: "Most people let them find out when they die because they don’t want to have the conversation... It’s a minefield of emotionality... an unbiased third party can really make a difference." (07:18, 07:40)

• Surprising Outcomes:
  Family members may actually agree on more than expected when guided properly.

  • Rick Kaler: "... when these difficult conversations are had, it’s surprising how often there may be agreement." (07:53)

5. Listener Resources & Call to Action

Timestamp: 08:05 – 08:34

• Getting Advice:
  Jill encourages listeners uncertain about how to start or broach estate planning topics to contact her show for guidance.
  • Jill Schlesinger: "If you’ve got a question about estate planning, maybe just don’t know how to get started ... get in touch with us." (08:08)

Notable Quotes & Memorable Moments

• On Superstitions:

  • Rick Kaler: "If I actually start drawing the documents, I’ll die." (03:43)
  • Juliet Caleb: "People are very superstitious. More than you would think." (04:05)

• On Family Dynamics in Estate Planning:

  • Jill Schlesinger: "It really makes you confront certain aspects of your family dynamic. I’m sorry, it just does." (04:43)

• On Getting Stuck:

  • Juliet Caleb: "Once this is done, at least they can put it away for a little while. The hard part is ... picking up the phone and calling. They’ve made it five steps just by doing that part of it." (05:51)

• On the Value of Third Party Guidance:

  • Rick Kaler: "Having somebody in the room that can help guide it ... can really make a difference." (07:40)

Timestamps for Important Segments

• 03:29 – 04:24: Emotional and superstitious roadblocks to estate planning
• 04:24 – 05:44: Family dynamics and the importance of dispassionate, expert guidance
• 05:44 – 07:03: Why the estate planning process stalls and how to push through
• 07:03 – 08:05: Discussing estate plans with family and leveraging third parties
• 08:05 – 08:34: How to get help and next action steps

Conclusion

Jill and her guests provide a candid exploration of estate planning’s emotional hurdles, common misconceptions, and practical tips for initiating and finishing the process. The episode urges listeners not to let fear, superstition, or discomfort with family dynamics keep them from tackling this vital financial task—and encourages seeking out professional and emotional support to get it done.

For related resources, webinars, or to ask your own questions, visit jillonmoney.com.