You can follow all the estate planning rules and still end up with the wrong plan. In this episode, Jill walks through a question from a young attorney who’s been handed traditional estate planning forms and is wondering whether they actually serve her clients. Jill break down how a standard trust structure can limit flexibility for families who don’t need estate tax planning, and how small adjustments can make a big difference. Estate planning isn’t about checking boxes. It’s about building something that works. 

New clients came in with two life insurance trusts—professionally drafted, signed, notarized, and organized in beautiful binders. There was just one problem: the trusts didn’t do anything.

In this episode, Jill breaks down what an irrevocable life insurance trust (ILIT) is, when it actually makes sense, and how it fails when no one follows through. This is a real-life look at the gap between having documents and having an estate plan that actually works.

When someone dies, there’s no master list of what they owned and no automatic system that pulls it all together. In this episode, Jill walks through what actually happens when families try to track down assets, why unclaimed property isn’t the safety net people think it is, and how a lack of organization can turn estate administration into a frustrating, years-long scavenger hunt. This is where estate planning meets real life and where most plans break down.

Agreeing to serve as an executor, trustee, or agent under a power of attorney often feels like the right thing to do but it’s also one of the most overlooked risks in estate planning. In this episode, Jill flips the perspective and walks through what you need to evaluate before you say yes to a fiduciary role in someone else’s estate plan. From compensation and liability to knowing when to step in and how to step out, this episode highlights the gap between estate planning documents and real-life execution. Because a well-drafted estate plan only works if the people named in it are set up to succeed.

Can you stop your child from inheriting money, even if the trust says they should? In this estate planning episode, we walk through a real-life scenario where a mother is trying to protect her son from receiving a large inheritance at the wrong time. Along the way, we break down how estate planning tools like trusts actually work in real life, what trustees can and can’t do, and why you can’t simply “use up” a trust to avoid passing money on. We also introduce a powerful (and often overlooked) tool, a power of appointment, that might allow you to adjust what happens next, even when a trust is irrevocable. Because sometimes the plan is set… but not completely locked.

What happens if you don’t name a beneficiary on your retirement account? Most people assume it goes to the estate. But that assumption can be dangerously wrong. In this episode, Jill walks through a real case where getting this wrong would have cost a surviving spouse more than $300,000, and explains what actually controls the outcome in your estate planning.

A viral Instagram reel claims California’s Proposition 19 “hijacks your kids’ inheritance.” In this Tuesday Triage episode, Jill walks through the facts behind the fear. Using a real-world example, she explains how California property taxes actually work, what changed under Proposition 19, and why federal tax rules like step-up in tax basis still protect many beneficiaries. This episode is about slowing down, adding context, and replacing social-media sound bites with real understanding.

A beautiful estate planning binder doesn’t mean your plan is complete, especially when business interests or stock grants are involved. In this Tuesday Triage episode, Jill Mastroianni unpacks a listener question about distributing a family business in a blended family and uses it to expose one of the most common estate-planning blind spots: assumptions about ownership.

Through real-world examples and practical guidance, Jill walks listeners through how to identify who actually owns a business interest, what that ownership really means, and why these details matter long before a crisis forces the issue.

What happens when an estate plan is technically correct—but doesn’t quite work in real life?

In this Tuesday Triage episode, Jill shares a moment from a client meeting where one simple, common-sense question changed an entire estate plan. Through a personal story and a real client scenario, she breaks down the differences between trusts and powers of attorney, and explains why questioning the expert can lead to a plan that actually works when it matters most.

This episode is about trusting your instincts, understanding your options, and remembering that estate planning is supposed to serve real people, not just legal theory.