Estate Planning Awareness

Summary

Jill on Money with Jill Schlesinger

Episode: Estate Planning Awareness

Release Date: October 24, 2025

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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.

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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)

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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)

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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

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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.

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

Transcript

[Rick Kaler]

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[Jill Schlesinger]

Today's episode is supported by what Should I Do with My Money? An original podcast from Morgan Stanley and Like Jill on Money, this podcast makes understanding money and getting advice about what to do with it less intimidating. You'll hear candid conversations from people just like you who have money questions just like yours. They talk to experienced financial advisors about their goals, worries and dreams, asking questions like can I retire early? Like really early? How do I leave a financial legacy for my special needs child? Menopause is making me feel wacky and it's shifting how I think about my money. Help. The conversations can get emotional, but they're always practical. Find what Should I Do with My Money? On your preferred podcast player and feel empowered and supported when it comes to managing your life and finances. Welcome to the Jill on Money show. It's Friday, October 24th. Hey, did you realize that it is National Estate Planning Awareness Week? I bet you didn't. I know these things. It's always nice to have some sort of awareness week where I am allowed to talk ad nauseam about one of my favorite topics. I know you think it's weird, but it is true. I love talking about estate planning because it's just one of those areas that once you do it, it's so much easier to update it. It's also nice to know that you've gotten one of those big pieces of your financial foundation taken care of. And I think there's no for me to celebrate Estate Planning Awareness Week than to give you a little bit of the interview that we conducted in our most recent webinar. It was with Juliet Caleb, who is an estate planning attorney in New York, and Rick Kaler, a fee only financial advisor as well as a financial therapist. How about that for a dual degree? He's based in South Dakota and they joined us for this webinar which was so helpful. And this topic, maybe more than all others, really does show that so much of our financial world is influenced by our emotions and that's one of the big hurdles that prevents us from getting our estate planning done. So here is a snippet of the webinar that we conducted with Juliet Caleb and Rick Kaler. And remember if you'd like to see the entire webinar, all you need to do is be a member of Jill on Money Live. 45 bucks for the next 12 months, access to the course, quarterly live webinars. Our next one is gonna be year end financial planning and tax planning. But you also get the back catalog like this interview and all the others that we've done. There's bonus audio and video content. Again, 45 bucks for the next 12 months. Jill on Money Live. Okay, here is the interview with Julia, Caleb and Rick Kahler. Rick, what do you do if you have a couple that or even an individual who's resistant to this process? How do you help people get over the hump? How do you help. How can we help people get over the hump when they are in that situation?

[Rick Kaler]

First thing that I think of is to become curious, you know, shaming people for not having it. You can normalize it that 68% of people don't have state plans or documents. But rather than try to convince them why, it's best to understand why and to really get curious about what it is. I've had all sorts of things come up, but one thing that I've had come up in the past is that, well, if I actually start drawing the documents, I'll die.

[Juliet Caleb]

Oh, that's very common.

[Jill Schlesinger]

Really?

[Juliet Caleb]

Yes. People are very superstitious. More than you would think.

[Jill Schlesinger]

Wow, I had no idea. That's incredible.

[Juliet Caleb]

Yeah, it's a real thing.

[Jill Schlesinger]

Okay. I don't think I ever heard that, but that's amazing. That's like people, they don't want to cancel their life insurance because they think if they do, the next day they're going to drop dead.

[Juliet Caleb]

Yeah.

[Jill Schlesinger]

Wow. Okay, so that's one thing. Okay, so curiosity, obviously a little compassion in this. Right. Because people are freaking out about it. You know, it's interesting, I think that when people are dealing with this, it really makes you. And the reason, again, the emotional part is it makes you confront certain aspects of your family dynamic. I'm sorry, it just does. So what that means is that if you're worried, like we have someone in the chat who's like, I'm worried that, like, my kids are bad with money. Or if you're worried to have a conversation with your parents because you're like, oh, if I find out they're in terrible financial situation, then I actually have to deal with that. Or if you find out that your parents have been hoarding all this money and you've been struggling, what does that bring up to you? All these things happen every day. Right. What the value I think of is involving an estate attorney or. Or a financial therapist or your financial planner, and ideally both, because it's. Rick, is that you have someone who is a dispassionate observer and expert. From your perspective, Juliet, when people come in, they know they're coming in to draft their estate documents. I imagine one of the harder things for you is to get them to complete the process, because doesn't it just get stretched out forever and ever?

[Juliet Caleb]

It does. It can.

[Jill Schlesinger]

And how do you move it along?

[Juliet Caleb]

Regular reminders. Very kind reminders. I think kind of going with the general philosophy that once this is done, at least they can put it away for a little while. This is the hard part, you know, the hard part is, you know, sending me an email or picking up the phone and calling. They've made it five steps just by doing that part of it. So I think. And then having a big conversation about their family and what they want to do, encouraging them because. Because I think by the time they read the drafts, and that's a place where things kind of get stalled, they've done so much of the hard work.

[Jill Schlesinger]

Right.

[Juliet Caleb]

And I think encouraging that and saying, you know, you've done this, it's hanging over your head. There is a huge emotional component. A lot of people believe, well, I've gotten it that far, so I've done this, and I've. 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. So I wish I had an easy answer. But I think being encouraging, being positive and explaining that the worst is over, then they can kind of close the chapter on this for a while.

[Jill Schlesinger]

Rick, should you have this, like, how do you bring your kids in? Let's say your kids are horrible with me. Do you bring them in and have this conversation with someone like you in the room to say, like, hey, look, this is what we're doing, or do you let them find out when you die?

[Rick Kaler]

Most people let them find out when they die because they don't want to have the conversation. There are hard conversations to what you alluded to, Jill. We bring in so much baggage into these discussions, you know, decades of history and relational history. It's a minefield of emotionality.

[Jill Schlesinger]

Yeah.

[Rick Kaler]

So having somebody in the room that can help guide it to your point, someone who's dispassionate, an unbiased third party, can really make a difference in exploring that and exploring why you may want to set up a trust, and a lot of times when these difficult conversations are had, it's surprising how often there may be agreement.

[Jill Schlesinger]

I am bad with money, right? I don't. I really don't want that responsibility. I do need help with that. That's so. It's so true. You're absolutely right. If you've got a question about estate planning, maybe just don't know how to get started. Maybe you're not really clear about how to broach the topic with members of your own family, get in touch with us. Go to jillonmoney.com, click the contact us button, write us a note, and of course, check the box if you'd like to join us on the air live. I very much encourage you to join us live when you're talking about estate planning because there's a lot of nuance to this topic. In okay, that's it. That's the program. You can subscribe to us on the Odyssey app or wherever you find your favorite podcasts. Our music is composed by Joel Goodman. Mark Talercio is our executive producer and king of all things Web, and we are distributed by Odyssey. Try to do something nice for someone else today. Change your work, change your wealth, change your life. Thank you for listening and we'll talk to you on Monday. Hey gang, here's the thing about wine. Some of the best bottles are not sitting on a store shelf. They're being crafted at small, independent wineries. But those wines can be so hard to find sometimes I wish I had a personal sommelier to guide me to find the best wines I normally wouldn't be able to access. Where's that handcrafted pinot that I've been craving? Well, Psalmsation's expert team seeks out incredible wines from top independent producers. These are bottles that you will not find in stores and on shelves. They aren't mass produced wines. They're handcrafted with care, using pure ingredients and meticulous winemaking. Whether you want a single bottle, a guided tasting experience, or an entire wine club membership, Psalmsation makes it easy to elevate your wine experience. Shop their [e-mail] jillonmoney that's somsation.com jillonmoney.

[Juliet Caleb]

Hi, I'm Nancy Cartwright. You may know me better as the voice of Bart Simpson on Simpsons Declassified, we're diving into the mysteries that keep the Simpsons forever young. Have you ever wondered how the Simpsons regularly predicts future events? Who better to ask than the show's creators, performers and writers? The celebrity guests be sure to follow and listen to Simpsons Declassified wherever you get your podcasts.