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What happens when the plan works perfectly on paper—but still doesn’t quite work in real life? Today, I share a moment from a client meeting where one simple question changed an entire estate plan. We’ll talk about trusts, powers of attorney, and why “that’s just how it’s done” often isn’t best answer. This episode is about trusting your instincts and asking the question that makes the plan better for the people who actually have to live with it.

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Welcome to the Death Readiness Podcast. This is not your dad’s estate planning podcast. I’m Jill Mastroianni, former estate attorney, current realist, and your guide to wills, trusts, probate and the conversations no one wants to have. If your Google search history includes, “Do I need a trust?” “What exactly is probate?” and “Am I supposed to do something with mom’s Will?” you’re in the right place.

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When I started my junior year of high school, I was on fire athletically. I’d had an incredible summer of training in the Adirondacks—running, biking, swimming—and working shifts at the local ice cream shop. I entered the national championship race the fall of my junior year undefeated.

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Then I had a terrible race.

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I finished 14th. And to me, that felt like failure. I had planned to win.

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So instead of resting, I decided the answer was simple: I needed to push harder.

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What I didn’t realize was that pushing harder had made my body vulnerable. I started feeling exhausted in ways that didn’t make sense. My high school had two floors, and I remember struggling just to walk from the first to the second. I kept wondering, Is this how it’s supposed to feel?

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My mom took me to our family doctor. She ran some tests and told me everything looked fine.

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So I doubled down. I told myself it was all in my head.

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Early in the summer heading into my senior year, I went out for a run on a steep rural road. Halfway through, I couldn’t do it. I started walking. And, I never walked.

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I’d been walking for maybe a minute when my mom pulled up beside me in her car. She never did that either. But that day, she did.

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By then, I’d trained twice at the United States Olympic Training Center with elite high school athletes. My mom called the physiologist from that program and asked if there was any bloodwork he’d recommend. One of the tests he suggested was for mononucleosis, or, mono—something that’s actually pretty common in high school students.

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We were in the Adirondacks for the summer, so my mom took me to the local doctor with a handwritten list suggested bloodwork from the physiologist.

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That office had a lab, so I sat in the hallway holding the lab slip. I looked it over—barely legible, as doctor’s scripts are known to be—but I didn’t see mono on the list. And I knew it was supposed to be there.

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The doctor walked by, and I stopped him. I asked, Did you include a mono test?

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He looked at the order and said, “No, I didn’t.”

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And then he added it.

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I was nervous to question him. But I did. And it mattered—because the bloodwork came back positive for mono.

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If I hadn’t looked at the order, if I hadn’t asked the question, the results would have come back normal. And I might have kept believing what others were telling me—that it was all in my head.

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Today’s Tuesday Triage is about moments like that.

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It’s about trusting your instincts and asking questions. It’s about what can change when you’re willing to question the expert.

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If you’re listening and thinking, I have questions—but I don’t even know where to start, that’s exactly why I created The Death Readiness Playbook. It helps you surface the right questions, understand the documents you already have, and spot the gaps before a crisis forces your hand. Learn more at deathreadiness.com/playbook. That’s deathreadiness.com/playbook.

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Today’s question comes from a client meeting I had last week. I’ve been working with a woman in her 70s—I’ll call her Linda—who asked a simple, common-sense question that shifted her estate plan in a way I hadn’t initially seen.

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Over the holidays, my travels took me to my dad’s house in the Adirondacks. Linda lives nearby. She became a client over the summer when my daughter and I were spending time there.

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Linda is single and has two adult daughters. She knew she wanted to get her estate planning in order, but the whole process felt too overwhelming to tackle on her own. That’s where I came in.

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Linda and I started at the beginning. We figured out what she owned and how it was titled. We talked through who she wanted making decisions for her if she couldn’t make them herself, and how she wanted her assets handled after her death.

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At the end of September, Linda and I met together with an excellent New York estate planning attorney. Just before Christmas, we received drafts of her estate planning documents.

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Because our holiday schedules lined up, Linda and I agreed to meet in-person on New Year’s Day to review those drafts together.

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I reviewed the documents in advance. Part of my role is making sure an estate plan doesn’t just work legally, but that it works in real life, for the person sitting across the table from me.

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Linda’s plan included a revocable trust, sometimes called a living trust.

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At its core, a trust is a legal arrangement where one person—the trustee—manages assets for the benefit of others, called beneficiaries. This arrangement is spelled out in a trust agreement, which functions like a contract: who gets what, when they get it, and under what conditions.

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A revocable trust is one that can be changed or undone during the creator’s lifetime.

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It can help avoid probate and make it easier to manage assets if the creator becomes incapacitated.

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Linda chose a revocable trust because she wanted to make things as simple as possible for her daughters—both while she’s alive and after she’s gone. Given those goals, her New York attorney recommended this structure.

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If you want a deeper dive on whether a revocable trust makes sense for you, I’ll link to Episode 19, Why You Need (or Don’t Need) a Trust, in the show notes.

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Here’s how a revocable typically works.

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When someone creates a revocable trust, they usually serve as the initial trustee. Linda is single, so she was named the sole trustee of her trust. If a married couple creates a revocable trust together, it’s common for both spouses to serve as co-trustees.

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Linda has two adult daughters who are responsible, capable, and—importantly—they get along. That combination is rare, and Linda wanted to take advantage of it.

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In the draft trust we were reviewing, Linda was the initial trustee, and her two daughters were named as successor co-trustees. Because her daughters communicate well and both have young families, everyone agreed that each daughter should be able to act independently as trustee. In other words, either daughter could step in and take action without needing the other’s signature. It would be critical that they continued communicating with each other.

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The trust provided that Linda’s daughters would step in as successor co-trustees in one of two situations: First, upon Linda’s mental incapacity, if that ever occurred. Second, upon Linda’s death.

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And like most well-drafted revocable trusts, this one included language spelling out how incapacity would be determined.

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Under the trust, Linda’s daughters would need either a court order or a written medical opinion confirming that Linda was under a legal disability—or, as the trust put it, that Linda was quote“suffering from diminished capacity that prevents her from giving prompt and intelligent consideration to financial matters and administrative decisions such that she is unable to serve as trustee.”

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This is a common arrangement, but as I’d soon find out, it would not have been a good fit for Linda’s situation.

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As I reviewed this section before our meeting, I made a couple of notes for myself.

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One was to ask Linda whether her doctor would even feel comfortable providing a written opinion about her mental capacity. The other was to ask the drafting attorney whether she had a standard form for that determination—something we could show Linda’s primary care physician and ask, very concretely, Would you be willing to complete this if Linda became unable to manage her own affairs?

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Because in practice, many doctors are hesitant to make formal capacity determinations. And I was concerned about the real-world consequence of that hesitation: I didn’t want Linda’s daughters to be forced into court, considering that Linda’s goal was to make things as easy as possible for them.

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As I started walking through those concerns, Linda stopped me.

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She said, “Don’t my daughters already have the ability to act immediately—without an incapacity determination?”

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She was right to ask.

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We had just finished reviewing her financial power of attorney.

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There are two basic types of financial powers of attorney: immediate and springing.

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An immediate power of attorney takes effect as soon as it’s signed. For example, the power of attorney I’ve given my husband Jeremy is immediate—he could act today if needed.

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That’s helpful because if I became incapacitated, he wouldn’t need a formal determination to step in and help. But there’s a tradeoff. Even while I’m fully competent, he legally has the authority to act—he could, in theory, sell our house without my knowledge.

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A springing power of attorney works differently. It only becomes effective after an incapacity determination. Often, that means that a physician must certify that the person can no longer manage their own affairs. Generally, individuals who don’t want anyone else to have access to their assets while they’re still mentally competent, choose a springing power of attorney.

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If you want a deeper explanation of powers of attorney, I’ll link to Episode 17, How Powers of Attorney Work, When to Use Them, and When It’s Too Late to Get One, in the show notes.

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In Linda’s case, after talking it through with me, her attorney and her daughters, she chose an immediate financial power of attorney. She named both daughters as co-agents, each with the authority to act independently.

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And here’s the key point: under that power of attorney, Linda’s daughters could step in and manage her affairs immediately. No incapacity determination is required.

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So when Linda asked whether her daughters already had that authority, the answer was yes—but only for assets titled in her individual name.

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What we were reviewing at that moment wasn’t her power of attorney. It was her revocable trust.

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And trusts work differently.

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A power of attorney governs assets owned in your individual name. A revocable trust governs assets you’ve transferred into the trust—like a home titled in the name of the trust.

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We’re dealing with the same people and the same goals, but it’s two different legal tools.

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And that’s where Linda’s question took us next.

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To avoid probate, Linda planned to transfer most of her assets into her revocable trust—everything except her retirement accounts, which already had beneficiary designations.

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That meant she would have two categories of assets: Assets still titled in her individual name, like her retirement accounts, managed by the agent under her power of attorney. And assets titled in the name of the trust, like her house, managed by the trustee of the revocable trust.

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Linda understood that structure. What she didn’t understand was why the trust required an incapacity determination for her daughters to take over but the power of attorney did not.

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Linda wanted one thing above all else: if something happened to her, she wanted her daughters to be able to step in immediately. She trusted them and she didn’t want them worrying about getting a doctor’s letter or going to court just to help her. That’s exactly why she chose an immediate financial power of attorney.

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So she asked the obvious question.

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Why shouldn’t the trust work the same way?

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That question changed everything.

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I had been focused on the mechanics—the way trusts are usually written and the way incapacity provisions typically work. Linda zoomed out. She saw the whole picture.

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And Linda has no formal training in trusts and estates law. She was using common sense. And she wasn’t afraid to question me—the so-called expert.

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I don’t know whether Linda felt comfortable asking because we were sitting at my dad’s dining room table, because we’ve known each other for more than a decade, or because she would have asked that question no matter what.

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But I’m grateful she did.

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Because when she asked, “Why are they different?” the honest answer was: they don’t have to be.

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So I told her, “You’re right, Linda. We can change this.”

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I reached out to the attorney and asked that the trust be revised so that Linda and her daughters would serve as co-trustees from the beginning, with each trustee able to act independently, just like under the power of attorney.

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We’d be clear with her daughters that there was no expectation they step in right away. But if their support was ever needed—because of incapacity or illness—they could act immediately. No medical letters. No court orders. No delays.

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I’m the expert. But Linda caught something I didn’t. The plan worked perfectly on paper. Linda made it work better in real life.

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And that’s the lesson here.

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Sometimes the most important question isn’t “Is this legally correct?” It’s “Why does it have to work this way?”

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When I was a teenager, asking one uncomfortable question changed everything. Years later, Linda reminded me how powerful that same instinct can be.

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Estate planning isn’t about memorizing rules or blindly accepting answers. It’s about understanding your options and speaking up when something doesn’t feel right. Because the best plans aren’t just legally sound—they’re built by people who are willing to ask the questions that makes them better.

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If this episode made you realize you want a plan that works in real life—not just on paper—The Death Readiness Playbook is a great place to start. It’s a practical, step-by-step system to help you organize information, understand your options, and make decisions your family can actually use when it matters. It’s just 27 dollars and you’ll find it at deathreadiness.com/playbook. That’s deathreadiness.com/playbook.

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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.

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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.

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