Educational content only. Not legal, financial, tax, or medical advice. Plan Your Passing is not a law firm and no attorney-client relationship is created here. Estate, probate, tax, and inheritance laws differ by country, state, and county. You are responsible for confirming what applies to you. Always consult a licensed attorney in your jurisdiction before acting on anything you read or generate on this site.
About Plan Your Passing
Built for the conversation no family gets a script for.
Plan Your Passing is the family-side platform for end-of-life planning. We are not a law firm. We are not a financial advisor. We are not an insurance carrier. We are the trusted layer between those professionals and the family that has to figure out the rest of it.
To make every family's end-of-life decisions clearer, kinder, and faster than the alternative. The legal industry built tools for documents. We build the system around the documents: the conversation, the scenarios, the scripts, the playbook for the day it actually happens.
The largest intergenerational wealth transfer in human history is underway. $84 trillion will move from baby boomers to Gen X and millennial heirs through 2045. Most families are not ready for the conversations, the documents, or the math. The legal sector serves the documents. Almost nobody serves the family.
Source: Cerulli Associates, U.S. High-Net-Worth and Ultra-High-Net-Worth Markets, 2022 report.
Founded by a licensed realtor with 15 years in the room when estates settle and 21 years sponsoring people through the hardest conversations of their lives. We are not a law firm. Not a financial advisor. Not an insurance carrier. We are the trusted family layer that did not exist before.
Founder
Roger Daniel Grubb
Roger has spent fifteen years as a licensed California realtor, most of those years in the East Bay — Pinole, San Pablo, Hercules, Richmond. The kind of work that doesn't make the trade magazines: a thousand-square-foot stucco bungalow in 1972 that becomes the seven-hundred-thousand-dollar inheritance in 2026. The kind of transaction where the listing call is also a grief call, and the buyers don't know that yet.
Which means he has been in the room for hundreds of estate settlements. The siblings who wouldn't speak to each other. The widow who didn't know where the deeds were. The estranged son who showed up the day after the funeral. The one with the key to the safe deposit box and the one with the key to the house and the one with neither. The mother who said the daughter could have the piano, and the brother who heard it differently, and the piano that sat in the foyer for fourteen months while the estate stayed open.
He kept noticing the same thing: the legal documents were almost always fine. The family system was almost always broken. The attorneys had done their part — wills, trusts, POAs, sometimes brilliant tax planning. But nobody had told the family how to actually have the conversation. Nobody had built the script for what to say when the brother stops returning calls. Nobody had given the executor a 30-day playbook for the work that goes way beyond the legal mechanics.
Roger has also been a recovery sponsor for twenty-one years. Which means he has sat with people through the hardest conversations of their lives — the conversation with a parent, the conversation with a sibling, the conversation with yourself. The recovery world teaches you that the script is everything. The exact words, said in the exact order, by a person who has done it before, is the difference between a breakthrough and a wall.
Plan Your Passing is what he wishes had existed when those families called. Not another estate-planning law firm. Not another life-insurance funnel. The platform that sits beside the family at the kitchen table and helps them figure out what to say, what to do, in what order, with what consequences.
Not a lawyer. That is the point.
Credentials
- Licensed California Realtor since 2010
- 21 years as a recovery sponsor (continuous sobriety)
- Author, Plan Your Passing: The Family Guide
- Founder, Plan Your Passing platform
Subject-matter focus
- Inherited-property real estate transitions
- Step-up basis and primary-residence exclusion
- Sibling conflict mediation and pre-fight conversations
- Executor playbooks and first-30-days work
- Blended-family estate dynamics
How we work
Six operating principles
These aren't aspirational. They're the rules we actually use to decide what to publish, how to write it, and what to charge for.
Plain English over legalese
If a sentence can be written in fewer or smaller words without losing precision, we use the shorter version. Lawyers write for other lawyers. We write for the family at the kitchen table on a Tuesday morning, often the day after a death, often before their coffee is done.
Composite case studies, not real-client stories
Every story you read on this site is a composite — common patterns combined into a representative example, with fictional names and locations. We never identify a real client. Even with permission, we don't, because it sets a precedent. Composites let us teach the lesson without ever putting a family in the line of fire.
Honest about what we are not
We are not a law firm. We do not draft binding legal documents. We do not provide legal, financial, tax, or medical advice. Every page on this site says so, clearly, in the legal disclaimer. The trade is that we say things lawyers can't say — about families, about money, about the conversations that actually have to happen.
Free for families. Paid by professionals who serve them.
Editorial content, AI tools, conversation scripts, state guides, and the 47-point checklist are free and stay free. Forever. Families never pay to figure out grief. We monetize the optional book ($19.99), the optional community ($47/mo), and the partner program for professionals ($97/mo). Trust monetizes for decades; ad revenue monetizes for months. The full model is laid out at /why-free.
Built in public
We tell you when we launch features, when we make mistakes, and when we change direction. The public stats page shows real subscriber counts, real customer counts, and real shipping cadence. No vanity metrics. No 'as seen on' badges from publications that haven't actually written about us.
Family relationships before assets
Every recommendation we make passes one test: does this protect the family relationships, even when it costs a few thousand dollars on a tax strategy that would have saved more? Most estate planning maximizes the asset transfer. We optimize for the family that has to live with each other after the transfer.
Timeline
How we got here
Roger gets his California real estate license. First estate-transition deal: a paid-off home in Pinole with three siblings who hadn't spoken in five years.
After his 100th estate-related transaction, Roger starts keeping a journal of every recurring family pattern. Notes that the legal documents were almost always fine. The family system was almost always broken.
COVID accelerates everything. Families realize they have no documents, no conversations, no plan. Roger writes a 60-page draft of what eventually becomes Plan Your Passing: The Family Guide.
Manuscript expands to 24 chapters. Roger starts using draft chapters with families as supplemental material in real transactions. Pattern: the chapters they read prevent the fights he used to mediate.
Plan Your Passing is built — first as a brand, then as a platform. Programmatic state-by-state content. Scenario walkthroughs. The 47-point checklist. Architecture for the next 5 years.
Public launch. Free Founding Member access for the first 10,000 families. Book and community at Founding-Member rates. Partner program opens to realtors, advisors, attorneys, and CPAs.
By the numbers
What is shipped
Updated continuously. Public stats page at /stats shows real signups and customers in real time.
For the lawyers in the room
What Plan Your Passing is not
We are not a law firm. We do not draft binding legal documents. We do not give legal advice. Every page on this site says so, clearly, in the legal disclaimer. Educational content only.
We are not a financial advisor. We do not recommend specific investments. We do not sell securities or annuities. We describe how the system works and what questions to ask the right professional.
We are not an insurance carrier. We do not underwrite policies. We help families understand what they need and we partner with vetted carriers and brokers when families ask.
We are not a CPA or tax preparer. We explain the rules that affect estate decisions (step-up basis, inheritance tax by state, IRA RMDs). We don't file your taxes.
We are the trusted family layer that complements all four. That is the entire thesis.
For press & partners
Building in the end-of-life adjacency. Open to white-label, content, API, and strategic-alignment conversations. Press kit available for journalists.