Episode 88: How to Overcome Estate Planning Jargon and Overwhelm
Episode 88
Host: Jill Mastroianni
How to Overcome Estate Planning Jargon and Overwhelm
The biggest obstacle to estate planning isn't procrastination. It's confusion and overwhelm. In this episode, Jill shares why she changed the way she practices law, the surprising lesson a surgeon taught her about communication, and why helping clients understand their estate plan is just as important as drafting excellent legal documents. Through stories about a graphic designer, AI, a 90-year-old client, and even her own financial planner, Jill explores how great professionals not only know their subject, they know how to explain it.
What You’ll Learn in This Episode
· Why confusion and overwhelm, not procrastination, keep many people from completing their estate plan.
· How Jill's approach to estate planning has evolved over the past 12 years.
· The importance of translating estate planning legal jargon into everyday language.
· Why AI is a valuable tool, but a poor substitute for professional judgment.
· How Jill uses AI in her own estate planning practice and podcast without letting it replace experience or critical thinking.
· The unexpected communication lesson Jill learned after thyroid cancer surgery.
· Why excellent estate planning documents aren't enough if clients don't understand what they're signing.
· Why Jill charges flat fees for estate planning and encourages clients to ask questions without watching the clock.
· The reminder that we're all experts at something and beginners at something else.
Resources & Links
Watch this episode on YouTube: https://youtu.be/1Ivqf4_izD4
Jill’s Estate Plan Audit: https://www.deathreadiness.com/audit
Jill’s Tennessee Estate Planning Services: https://www.deathreadiness.com/estate-planning-solution
Connect with Jill:
· Website: DeathReadiness.com
· Email: jill@deathreadiness.com
· Learn more about Jill’s solutions
· Subscribe to the Death Readiness Dispatch!
· Ask a question for Tuesday Triage
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The biggest obstacle to estate planning isn’t procrastination. It’s confusion and overwhelm. Today, I’m sharing why I stopped practicing law the way I was taught, the surprising lesson a surgeon taught me about communication, and why I believe helping clients understand their estate plan is just as important as drafting it. If you've ever put off estate planning because it felt like too much, this episode is for you.
Welcome to The Death Readiness Podcast. This is not your dad’s estate planning podcast. I’m Jill Mastroianni — estate planning attorney, death readiness guide, and your translator for wills, trusts, probate, and the conversations most families avoid. If you’ve been wondering things like, ‘Can a trust protect what I leave to my children?’ ‘What happens if I give someone power of attorney over me?’ and ‘How can I help my parents while respecting their independence?’ You’re in the right place.
When I first started practicing estate planning, I practiced the way I'd been taught. Meet with the clients. Draft the documents. Email them the drafts with a summary. Schedule a signing. Done. That's how I practiced for years, including when I was one of about 2,000 attorneys at a very large law firm. But I don't practice that way anymore.
It's not necessarily because I think that process is wrong. It's because over the last 12 years I've realized that preparing good legal documents is only part of my job. The other part is making sure my clients actually understand what they're signing and why.
The longer you've worked in any profession, the easier it is to forget what it felt like before you knew any of it. The words become second nature. The abbreviations make sense and you stop noticing how much specialized language you've actually accumulated.
But the people sitting across from you haven't spent years immersed in your world. They're hearing many of these terms for the very first time. Part of being good at your job is remembering where you started and explaining what you know today using the language you had before you learned all the jargon. That's one reason I always run my podcast episodes by my husband before I record them.
He's a software engineer. If I say something that doesn't make sense to him, I rework it until it does.
I'm making this podcast for people who have questions about wills, trusts, probate, and powers of attorney, not for experienced estate planning attorneys.
I've realized there are two main reasons for not doing something challenging. #1 – You don’t know where to start, and #2 – There’s just too much to do.
Here’s a recent situation where I felt like this. I'm getting ready to officially launch Mastroianni Legacy Law, and I wanted to make sure the messaging across my law firm, The Death Readiness Podcast, my website, social media, and my Google Business Profile all felt consistent.
My sister-in-law Bethany is an incredibly talented graphic designer and visual communicator. I asked if she'd help me think through how to better connect—but also distinguish—The Death Readiness Podcast and Mastroianni Legacy Law online.
She sent me two very thoughtful emails with color palettes, design ideas, layout suggestions, and messaging recommendations. And I stared at them. I knew there were good ideas in those emails but I just couldn't process them.
Design is a different language to me. So I emailed Bethany and said, "I can tell you've put a lot of thought into this, but I'm overwhelmed. Can we sit down and go through it together?" We did. She explained why she was recommending each change. I asked questions. We talked through the options. She made a few revisions.
And everything made sense. Bethany didn't change the quality of her ideas. She just changed how she communicated them. I think that's exactly what happens with estate planning. Some people don't move forward because the language feels foreign. Wills. Trusts. Powers of attorney. Beneficiary designations. Fiduciaries. None of those words are part of everyday conversation.
Other people understand the words just fine, but they’re overwhelmed. The stack of papers. The binders. The draft documents. The summary and the decisions all feels like too much.
And when you're both confused and overwhelmed, it's really easy to decide you'll deal with it later, or look for a shortcut.
Today, for a lot of people, that shortcut is AI. I have had clients upload their estate planning documents into ChatGPT or Claude with a prompt like, "Tell me if this is a good estate plan." Then they'll copy and paste the AI response into an email to me that simply says, "I gave the documents to ChatGPT. Thoughts?"
Please don't do that. And I don’t say that because I'm against AI. Quite the opposite. I use AI every day. For example, I might use ChatGPT to help soften the tone of an email. AI helps me communicate what I actually mean.
I also use legal AI to make my legal research more efficient and occasionally to suggest drafting language. But even with software that costs far more than ChatGPT or Claude, I still have to verify the legal sources, evaluate the suggestions, and decide whether they actually make sense. AI doesn't replace my experience but it does make me more efficient.
I think that's where people sometimes get tripped up. AI works best as a collaborator, not as a substitute for judgment. And it definitely isn't a copy-and-paste communication tool. Let me show you what I mean.
After I record each podcast episode, I generate a transcript using AI built into my recording software. Then I upload that transcript into ChatGPT and give it a very specific prompt to create a title for the episode. I don't simply say, "Give me a title."
Instead, I tell it who my audience is. I explain the feeling I want the title to create. I tell it that I prefer titles that start with "Why," "How," or "What You Need to Know." I tell it to avoid colons and em dashes. I even give it a 61-character limit.
It usually gives me ten or so suggestions. Sometimes I like one. Sometimes I ask for more variations. And if I don't like any of them, I change my prompt or come up with something myself.
The title I ultimately choose might be one ChatGPT suggested, or it might be one that its ideas inspired. But I'm still the one deciding what best communicates the message I want you to hear. That's the important part. AI isn't driving the conversation. I am.
If I simply uploaded my transcript, accepted the first title it gave me, and never thought about it again, I'd be letting AI decide what I was trying to communicate. And if I gave you all ten suggested titles and said, "You pick," you'd probably wonder whether I even knew what I was trying to say. The same thing happens when clients send me pages of AI-generated questions without first thinking about what they're really trying to understand.
I ask ChatGPT for podcast title ideas, I don't let it decide what I mean. I decide what I want to say, and AI helps me say it better. That's one reason I even use AI when I'm outlining these podcast episodes. The first way I explain something isn't always the clearest way. Sometimes it's too lawyerly. Sometimes it's a little too "businessy." I don’t want to sound like a legal textbook.
My goal not to sound like a legal textbook is partly inspired by an experience I had 6 years ago. I had recently undergone surgery to remove a cancerous nodule from my thyroid. Thankfully, the surgery went very well and the cancer was completely contained in that one small nodule.
When I went back for my follow-up appointment, the waiting room was full of people receiving cancer treatment. Unlike me, many of the people waiting there were very, very sick. It was an emotionally heavy environment.
When the surgeon came into the exam room, she removed the bandage from my neck and very matter-of-factly said something like, "We did remove cancer. It was cancer." I was startled at the word “cancer” and didn’t say a word. She looked confused and asked, "You are Jillian Mastroianni, aren't you?" I said I was. I don't remember much else about the appointment because my brain had stopped listening.
And I don't tell this story because I think my surgeon did anything wrong. In fact, I think she was exceptional. Her name was Carmen—the same name as my dad—and she performed exactly the surgery I had hoped for. Most surgeons would have removed my entire thyroid. She was skilled enough to remove only the portion that needed to come out.
She was outstanding at surgery. We just had completely different perspectives. She was speaking from the perspective of someone who treats cancer every day. I was hearing those words as someone who wasn’t ready to have them applied to me.
I came away from that experience with my surgeon thinking about two separate goals. The first is to be excellent at what you do. The second is to make sure the person sitting across from you actually understands what you’re trying to say. I strive to do both.
Of course I want to create excellent estate plans. But I also want my clients to understand what I'm recommending, why I'm recommending it, and to feel comfortable asking questions until they're confident they're signing documents that truly reflect what they want.
My job is to remove stress, not add to it. I recently started working with a woman who is almost 90 years old. I'll call her Linda. Her husband passed away about a year ago. He had always handled the finances and the paperwork. Now all of that responsibility had landed in her lap.
When I arrived at her home, we started pulling binders and folders off the shelves. She kept apologizing because she didn't know what she had or how it all fit together. I said, "Linda, don't apologize. This is exactly why I'm here. We're going to figure out what you have. We're going to make sure the right people are in place to help you if you ever need it. And we're going to make sure everything you've worked so hard for ends up exactly where you want it to go." Linda didn’t need someone to simply draft documents. She needed someone to help her get unstuck.
And that's the practice I'm trying to build, a practice that breaks down the language barrier, doesn't overwhelm people with paperwork, and welcomes questions instead of making people feel like they're slowing things down.
I also know that hiring an attorney is a significant investment. Once someone hires me, I want the stress to start going away, not to increase every time they have a question. That's one of the reasons I charge a flat fee for estate planning instead of billing by the hour. I never want a client sitting at home wondering, "Is this question worth another six minutes of my attorney's time?"
Once you become my client, we're on the same team. We're going to work through it together. Right now, I practice estate planning in Tennessee, and I hope to add Michigan very soon. If you're outside Tennessee but you're looking at your existing estate plan and wondering, "Do I even understand what I have?" that's exactly why I offer estate plan audits. We review your current documents together, make sure you understand them, and identify any changes you might want to discuss with an attorney licensed in your state.
Estate planning is my thing. But do you know what I need help with? Almost everything that isn't estate planning. My daughter recently set up my printer because I couldn't figure it out. My neighbor's granddaughter is helping me track down the missing piece to my ring light. And despite my very Italian last name, if I'm left to cook for myself, there's a very good chance dinner will be an English muffin.
Last week I met with my financial planner, who's also a good friend. About halfway through the meeting she stopped and asked, "Are you okay? You look concerned." I laughed and said, "I'm not concerned. I'm just really bored."
There were numbers. Then more numbers. Then somehow... even more numbers. I was trying so hard not to look bored that apparently I looked worried instead. She laughed, changed how she was explaining things, asked me a few questions, and suddenly I was back in the conversation.
She met me where I was. And I realized she'd done exactly what I've been talking about in this episode. She didn't become less knowledgeable but she became a better communicator.
We're all experts at something. And we're all beginners at something else. My clients don't expect me to know how to design a website, fix a printer, or cook dinner. I don't expect them to understand trusts, probate, beneficiary designations, or powers of attorney. That's okay.
None of us has to know everything. We just have to know who to ask. If you've been putting off your estate planning because it feels confusing or overwhelming, don't assume the problem is you. Maybe you just haven't found someone who's willing to slow down, answer your questions, and explain it in a way that makes sense.
If today's episode made estate planning feel just a little less overwhelming, then it accomplished exactly what I hoped it would. If you're in Tennessee and you're ready to create or update your estate plan, I'd be honored to help.
If you're somewhere else in the country and you'd like help understanding the estate plan you already have, that's exactly why I offer estate plan audits. Sometimes you don't need to start over. You just need someone to help you understand what you already have. I'll include links to both in the show notes.
Thanks for listening today.
This is Death Readiness, real, messy and yours to own. I’m Jill Mastroianni and I’m here to help you sort through it, especially when you don’t know where to start.
Hi, I'm April, Jill's daughter. Thanks for listening to The Death Readiness Podcast. While my mom is an attorney, she’s not your attorney. The Death Readiness Podcast is for educational and entertainment purposes only. It does not provide legal advice. For legal guidance tailored to your unique situation, consult with a licensed attorney in your state. To learn more about the services my mom offers, visit DeathReadiness.com.
