Plan Your Passing

The Family Guide

By Roger Daniel Grubb, Licensed Realtor

Copyright

Copyright © 2026 Roger Daniel Grubb. All rights reserved.

No part of this book may be reproduced, distributed, or transmitted in any form or by any means, including photocopying, recording, or other electronic or mechanical methods, without the prior written permission of the publisher, except in the case of brief quotations embodied in critical reviews and certain other noncommercial uses permitted by copyright law.

First edition, 2026. Published by Plan Your Passing, LLC. planyourpassing.org

ISBN (Paperback): TK ISBN (eBook): TK

Disclaimer — Read This First

I am a licensed realtor. I am not a lawyer, a CPA, a financial advisor, or a tax professional. Nothing in this book is legal advice, tax advice, investment advice, or a substitute for professional counsel for your specific situation.

What this book is: a plain-English walk-through of how estate planning actually works in American families — the conversations, the paperwork, the fights, the taxes, and the day-it-finally-happens reality — written by someone who has spent fifteen years in the rooms where these things play out.

What this book is not: a replacement for an attorney licensed in your state. State laws differ. Your family is unique. The examples in this book are composites and illustrations, not prescriptions. Before you sign anything, before you file anything, before you move money anywhere — if the stakes are real, talk to a professional.

What's new in this edition (2026)

If you've read an estate-planning book or article more than a year old, several things have changed that you should know before you go further:

Federal estate tax exemption is now $15M per individual / $30M per married couple. The 2025 One Big Beautiful Bill Act (OBBBA) made the high exemption from the 2017 Tax Cuts and Jobs Act permanent, AND stepped it up. The "2026 sunset" landmine that pre-OBBBA estate-planning books warned about did not happen. Effective 2026, the exemption is permanent and indexed annually for inflation. If you did expensive "panic-gift" planning in 2024-2025 to lock in the prior $13.99M before it sunset to $7M — that planning is still valid, but it wasn't strictly necessary.

Iowa fully repealed its inheritance tax effective January 1, 2025. If your sources still list Iowa among the inheritance-tax states, they're out of date. There are now five states with inheritance tax: Kentucky, Maryland, Nebraska, New Jersey, Pennsylvania.

SECURE Act 10-year rule final regulations were issued by the IRS in July 2024. The key clarification: if you're a non-spouse beneficiary of an IRA from someone who was already taking required minimum distributions (RMDs), you must take annual RMDs in years 1-9 of the 10-year period AND fully empty the account by the end of year 10. Pre-2024 there was ambiguity about whether the annual RMDs were required; the final regs say yes.

State estate-tax thresholds are still much lower than federal. Oregon ($1M) and Massachusetts ($2M with cliff structure) remain the most exposing. Even Boston-area middle-class families now routinely cross the Massachusetts threshold thanks to real-estate appreciation. Federal isn't the only worry — see Chapter 23 and Appendix A.

These changes are reflected throughout this edition. Where a number appears, it's current as of publication.

When this book says "talk to an attorney," I mean it. When it says "this is the part where you need a CPA," I mean that too. The whole point of knowing how the machine works is so you can hire professionals intelligently and ask the right questions — not so you can do it yourself and hope.

Laws change. Tax thresholds change. Major recent events captured in this edition: the 2025 One Big Beautiful Bill Act (OBBBA) made the federal estate tax exemption permanent and stepped it up to $15M per individual ($30M per couple) effective 2026; Iowa's inheritance tax was fully repealed effective January 1, 2025; the IRS finalized SECURE Act 10-year-rule regulations in July 2024. Numbers and rules cited in this book reflect what I understood to be current as of the publication date. If you're reading this more than 12 months after publication, verify the specific dollar amounts and statute references before acting on them. Estate planning is state-law-driven; your licensed attorney is the authoritative source for your specific situation.

Dedication

For my father, who never sat me down. For the families who taught me what happens when no one does. And for Erica — who keeps me accountable to say the hard thing before it's too late.

A Note on the Stories in This Book

Every family story in this book is true in spirit. Every name, location, and identifying detail has been changed or composited across multiple cases. If you think you recognize yourself, you don't — you recognize your neighbor, your cousin, your own family, and a thousand others. That's the point. These stories are not special. They are what happens in ordinary American families every single day.

The people in these stories did not fail because they were bad or stupid or cold. They failed because nobody had ever told them how the machine worked. That is the gap this book is trying to close.

How to Read This Book

You do not have to read it straight through. You can, and some people will. But most people won't, because most people come to estate planning in the middle of a crisis — a parent's diagnosis, a sibling's phone call, a lawyer's letter. Here is how to use this book in the real situations you are probably in.

If a parent has just died and you have no idea what to do: Start at Chapter 11 ("The First 24 Hours"). Then read Chapter 12 (the executor's job) and Chapter 13 (probate). Come back to the rest later.

If a parent is aging and you know "the talk" is coming: Start at Chapter 1 ("The Conversation You've Been Avoiding"). Then read Chapters 2–5 on the core documents. Then go to Chapter 15 (why siblings fight) and skim Chapter 18 (special situations).

If you are the one planning your own estate: Read Chapters 1–10 in order. Then skip to Chapters 23–25 (taxes), then 26 (ethical will). Come back to the people chapters (15–18) before you finalize your plan.

If you are in a blended family: Chapter 17 is load-bearing. Do not skip it. Read Chapter 5 (beneficiary designations) and Chapter 16 (fairness trap) alongside it.

If you are already in a family fight: Chapter 22 (mediation) comes first. Then Chapter 15. Then, reluctantly, Chapter 20 (choosing an attorney).

The complete checklist in Chapter 30 works as a one-page map of the whole book. If you only ever read one chapter, read that one.

Before You Turn the Page

Most of the pain in estate planning is not legal. It is relational. The documents matter, but the conversations matter more. The tax code matters, but the trust between siblings matters more. The house is the most expensive thing on the balance sheet, but the wedding ring is the thing that will ruin Thanksgiving for the next twenty years.

This book takes both seriously. The mechanics are here — wills, trusts, probate, taxes, the first 24 hours, the 100-item checklist. And the humans are here — the sibling who was always the favorite, the stepparent nobody warmed up to, the adult child who hasn't called in three years but will show up for the reading of the will.

If you do the documents without the conversations, your family will fight. If you have the conversations without the documents, the fight will be legal and it will be worse. This book is about doing both.

Turn the page. Let's get to work.

— R.D.G. Redding, California Spring 2026