Grammy puts sugar and butter on her pancakes.
My daughter, who is four, watches her do this with the kind of focus only a small child can manage. Then she looks up and asks, "Grammy, why are you doing that?"
My wife Elise is sitting across from them, drowning hers in maple syrup. Three generations at one breakfast table, and three completely different ways of eating the exact same thing.
Grammy laughed and said something about how that's how her mother always made them. How they'd sit at the kitchen table on Saturday mornings, and that was just how it was done. Sugar, butter, the whole routine.
My daughter didn't ask a follow-up question. She just went back to eating. But I sat there thinking about what would happen to that story if Grammy hadn't been here to tell it. If nobody had ever asked. If that little piece of who we are just quietly disappeared because no one thought to bring it up over breakfast.
Families that talk openly about their values, traditions, and wishes are far more likely to successfully transfer wealth across generations. According to the Williams Group, a family wealth consultancy, 70 percent of wealth transfers fail by the second generation, and 90 percent fail by the third. The primary cause is not bad investments or poor tax planning. It is a breakdown in communication and trust within the family. The families who lose their wealth are overwhelmingly the families who never had the conversation.
And it almost always starts with the small stories.
The Little Stories Disappear First
Nobody wakes up one morning and decides to erase the family history. It happens slowly. Grammy's pancake recipe doesn't get written down. The reason Grandpa worked doubles at the plant never gets explained to the grandkids. The story of why your parents never took vacations, why they saved every dollar, why they wanted you to go to college and maybe do something different with your life. Those stories feel so obvious to the people who lived them that they forget other people don't know.
But they don't.
Your kids don't know why the money is there. They don't know what it cost. They don't know about the decades of grinding it out so they could have choices their parents never had. And if nobody tells them, they'll make assumptions. They'll think it was easy. Or they'll think it doesn't matter. Or they simply won't think about it at all until a lawyer calls and says there are decisions to make.
I work with retirees every day at American Retirement Advisors in Scottsdale, Arizona, and I can tell you from hundreds of conversations that the families who talk are the families who thrive. Not just financially. Emotionally. The ones who sit down and say "here's why we did what we did" are the ones whose kids and grandkids actually understand the weight of what's being passed down.
The ones who don't talk? They leave behind what I've started calling quiet chaos.
"It's Pretty Well Taken Care Of"
I've watched this play out closer than most people realize. Two people on our own team lost parents who said the words every family dreads in hindsight: "Oh, it's over there. It's pretty well taken care of."
It wasn't.
What followed wasn't one year of sorting things out. Or two years. It was three years of wasted hours and misery. Legal questions nobody could answer. Documents nobody could find. Wishes nobody could confirm. And the worst part? After all of it, the memory of the parents was clouded. The adult children weren't sitting around telling stories about Mom and Dad. They were buried in unfinished, unresolved challenges that consumed every family gathering for years.
That phrase, "it's pretty well taken care of," might be the most dangerous sentence in estate planning. Because it means nobody had the real conversation. It means the hard stuff got skipped, and everyone assumed it would work itself out.
It doesn't work itself out.
One of our clients called in and said something that stopped me: "We really, really need to get started with inheritance planning because my husband is in poor health and we have to get something going. We don't even have a will." That call came not at the beginning of a planning journey, but when crisis was already at the door.
How to Talk to Family About Inheritance (Without a Spreadsheet)
Most people think the inheritance conversation starts with documents. A will. A trust. A list of accounts. And those things matter. But they're not where the conversation starts.
The conversation starts at breakfast.
It starts when your daughter asks Grammy why she puts butter on her pancakes and Grammy says, "Because that's how my mother always made them." That answer carries more weight than any legal document. It says: I come from somewhere. I carry something forward. And I want you to know about it.
The financial version of that story is no different. Why did Grandpa work the job he worked? What did your parents sacrifice so you could have the life you have? What do they want to happen to what they built when they're not here anymore?
These aren't uncomfortable questions. They're generous ones. And they don't have to happen in a formal meeting. They can happen over pancakes. Over a walk. Over a holiday weekend when three generations are in the same room and someone finally says, "Let me tell you about how we got here."
Here's a simple way to start:
- Start with the story, not the money. Tell your kids or grandkids why you made the choices you made. The career. The sacrifices. The values behind the numbers. The money makes more sense when it has a story behind it.
- Name who gets what, and why. One of our clients is dividing her estate three ways: one-third to each of her two surviving daughters, and one-third to the children of a daughter who passed away. That decision IS the family story. It says: nobody gets forgotten. But she had to say it out loud for it to mean anything.
- Talk about your wishes while you can. Another client built a farm for her son. He moved to Malta. Now she's reworking her entire plan because the original assumptions don't hold anymore. Life changes, and the plan has to change with it. That conversation only works if it happens while everyone is still at the table.
- Write down your passwords. I asked a room of 20 people at one of our workshops: "Can you right now take out a pen and write down your username and password with 100 percent confidence that you have it right?" Four people raised their hands. Four out of twenty. That means for the other sixteen, a lifetime of photos, documents, and digital records disappears the moment their phone locks and nobody knows the code.
What Family Legacy Planning Really Means
Most people hear "legacy planning" and think it's a fancy word for estate planning. It's not. Estate planning is about documents. Legacy planning is about meaning.
Estate planning says: here's the will, here's the trust, here's who gets what.
Legacy planning says: here's why. Here's the story of this family. Here's what we value. Here's what I hope you'll carry forward, whether that's a business I spent 30 years building, or a recipe for pancakes that goes back three generations.
The families who do both are the ones who keep their wealth and their identity intact across generations. The ones who only do the paperwork? They might transfer the assets. But they lose the thread that ties it all together.
According to the American Bar Association, roughly 55 percent of American adults do not have a will or any estate planning documents. That means more than half the country is leaving every decision to a court that doesn't know their family, their values, or their story. The judge who handles your estate has never tasted Grammy's pancakes. And that judge will never know why that recipe mattered.
What Happens When Nobody Has the Conversation
When a family doesn't talk about inheritance, the consequences are not abstract. They're specific and they're painful.
Here's what I've seen happen, and what the data confirms:
- Probate. Most people don't realize that a will still goes to probate. I've heard an estate attorney in our office say it clearly: "I have had a lot of clients say 'I have a will, I'm good to go.' You've got the basics. But do you realize that your stuff goes to probate?" The look on their faces tells you they didn't know.
- Homes pulled out of trusts. During the 2020 and 2021 refinancing boom, countless homeowners pulled their homes out of their trusts to refinance because that's what the bank required. Then nobody put the home back. One family went 18 years before discovering the house was no longer in their trust. All that planning, undone by a single refinance nobody followed up on.
- The wrong people making decisions. Without a clear plan, the state decides who inherits. Intestate succession laws don't know that your daughter loved that rocking chair. They don't know that your son wasn't responsible with money. They don't know that you wanted the grandchildren of your daughter who passed away to be taken care of. The law applies a formula. Families apply love.
- Digital lives that vanish. Photos. Emails. Financial accounts. All locked behind passwords nobody else has. The stories those files contain are irreplaceable, and they're one locked phone away from being gone forever.
Every one of these outcomes is preventable. Not with a bigger portfolio. With a conversation.
Grammy's Pancakes Are the Opening
I'm not going to sit here and tell you that watching my mother put butter on her pancakes was a spiritual experience. It was breakfast. It was ordinary. It was a four-year-old asking a question and a grandmother giving an answer she probably gave without thinking twice.
But that's exactly what makes it important. The small, ordinary moments are where family identity lives. And if we don't protect them, if we don't pass them down, they vanish as quietly as they arrived.
The same is true for the money. If you don't talk about where it came from, what it cost you, and what you want it to do for the people you love, then someone else will make those decisions for you. A court. A formula. A process that doesn't know your family's name, let alone your pancake recipe.
You don't need a formal meeting. You don't need a lawyer in the room. You need a moment. Maybe it's a holiday weekend. Maybe it's a visit from Grammy. Maybe it's a question your kid asks that you weren't expecting.
That little question might be the spark you need to have the bigger conversation. About where the money came from. Who it's for. And what happens to it when you're not here to explain.
Don't wait until someone else has to figure it out. Tell the stories. Have the conversation. And while you're at it, write down your passwords.
What Families Actually Ask Us About Inheritance
How do you talk to family about inheritance? Start with the story, not the money. Share why you made the choices you made, what you sacrificed, and what you value. Then explain your wishes clearly: who gets what, why, and how. A family meeting does not need to feel like a legal proceeding. Some of the best inheritance conversations happen over a meal or a holiday visit.
What is the difference between legacy planning and estate planning? Estate planning focuses on the legal transfer of assets through wills, trusts, and beneficiary designations. Legacy planning includes those tools but goes further by addressing the values, stories, and wishes behind the money. Estate planning answers "who gets what." Legacy planning answers "why."
What happens to your estate if you don't have a will? Without a will, your state's intestate succession laws determine who inherits your assets. A court appoints an administrator, and the legal process of probate can take months or years. Your family's wishes, relationships, and circumstances are not considered. According to the American Bar Association, roughly 55 percent of American adults do not have estate planning documents.
When should you tell your kids about your inheritance plans? Before a crisis forces the conversation. The best time is when you are healthy, clear-headed, and able to explain your reasoning. Waiting until a health event or emergency often means decisions are made under stress, without the context your family needs to understand your wishes.
Why is a family meeting important for estate planning? Because the alternative is silence. Research from the Williams Group shows that 70 percent of wealth transfers fail by the second generation, primarily due to breakdowns in family communication and trust. A single conversation about your values, your documents, and your wishes can prevent years of confusion, legal costs, and fractured relationships.
This article reflects the personal views of the author based on years of experience in the retirement planning industry. It is intended for educational purposes and should not be considered personalized financial, tax, or legal advice. Please consult a qualified financial advisor, tax professional, or attorney before making decisions about your estate plan, inheritance, or legacy planning.
About the author: Ian Schaeffer is Chief Operating Officer at American Retirement Advisors in Scottsdale, Arizona. He lives in Amesbury, Massachusetts with his wife Elise and their two children. He thinks about pancakes more often than a COO probably should.
Disclaimer: The information in this article is for educational purposes only and does not constitute tax, legal, or investment advice. Tax laws change frequently, and individual circumstances vary. American Retirement Advisors does not provide tax or legal services. Before making any tax-related decisions, consult a qualified CPA, tax attorney, or financial planner who can evaluate your specific situation.