One of the things I've learned over the last twelve years is that people rarely avoid estate planning because they don't care. More often, it’s because it’s really hard to make sense of something that feels unfamiliar.

Death Readiness Dispatch
July 22, 2026

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Hi there,
 
One of the things I've learned over the last twelve years is that people rarely avoid estate planning because they don't care. More often, it’s because it’s really hard to make sense of something that feels unfamiliar.
 
There are new legal terms, important decisions and stacks of documents. And somewhere along the way, the whole process starts to feel bigger than it really is.
 
Of course, this doesn't just happen with estate planning. It happens any time we're beginners. I recently met with my financial planner. Halfway through our 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.
 
She could tell she'd lost me. So she changed how she was explaining things, asked me a few questions, and I was back in the conversation. She didn't become less knowledgeable but she became a better communicator.
 
That conversation reminded me of something I think about often. The longer you've worked in any profession, the easier it is to forget what it felt like before you understood all the jargon. We all become fluent in a language our clients don't speak.

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The stories that changed how I practice law

That's why I've changed the way I practice law. Preparing good legal documents is only half my job. The other half is making sure my clients actually understand what they're signing. Understanding creates confidence, and confident people move forward.
This week, I share:
Why I stopped practicing law the way I was taught,
The unexpected lesson a surgeon taught me about communication,
Why I use AI differently than many people expect,
And the story of a 90-year-old client who reminded me that sometimes people don't need more information, they need someone to help them get unstuck.
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If you've been putting off estate planning because it feels confusing or overwhelming, don't assume the problem is you. Maybe you just haven't had someone explain it in a way that makes sense.
 
If you're in Tennessee, I'd love to help you create an estate plan that's tailored to your family, and make sure you understand every recommendation along the way.
 
If you already have an estate plan, but it's been years since you looked at it (or you've never really understood it), that's exactly why I offer Estate Plan Audits. We review your existing documents together, translate the legal language into plain English, and identify the questions worth asking before you make any changes.
 
An estate plan only brings peace of mind if you understand it.
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Thanks for being here.
Jill
 

 
PS: This week's blooper reel includes me trying (unsuccessfully) to explain to my dog Hopper that podcast recording isn't an interactive activity.
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Royal Oak, MI 48067, United States