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Estate planning is the thing most people avoid. I’ve spent the past three months of my life up to my eyeballs in it for our own family. Around dining room tables. In rooms. On the phone. Via email.
I’ve spent my career talking to people about it. Wills and trusts. Beneficiary designations and powers of attorney. Guardianship provisions and healthcare directives. Account titling and charitable giving. You name it, I’ve asked my clients about it.
And yet. In a world where people pay me for my advice, and where I have commanded multi-million dollar operating budgets, I still feel like the child in our family screaming into a void about the need to get this done.
Reader, this is the hardest part about giving out “free” advice to family members. When there’s no skin in the game, you can’t control the outcome, and it’s harder to provoke action.
So I nag. And I push. And I cajole.
Clients are much more responsive. But sometimes, as an advisor, we have to nag them too. Lately these conversations have gotten a lot more personal as I’ve found myself sitting on the other side of them with people I love from varying generations and different life experiences: who should be in charge, who will take care of whom, what happens to a surviving spouse, whether the person someone wants to put in charge is actually capable of doing the job.
And I’ve realized there’s a part of estate planning we don’t talk about very often: Your estate plan isn’t only a plan for what happens to your money.
It’s a plan for what you’re asking other people to carry.
And if you’re an adult child trying to help your parents or grandparents get their affairs in order, that may be the most important place to start.
Don’t Start With “Do You Have a Will?”
While it’s an obvious question, and yes, any adult member of your family should have one, a better place to start is:
If something happened tomorrow, would we know what to do?
This isn’t just about death. It’s also about injury, strokes, dementia, hospitalization, and any circumstance in which a person can’t make decisions for themselves.
If one parent dies and the other suddenly has to manage finances they haven’t touched in thirty years. Who can legally act? Where does the money come from? Who pays the bills? Who owns the house? What debts exist? What income continues? Who can make healthcare decisions? Where are the documents? Who is the attorney?
And does the person named in the estate plan even know they’ve been given the job?
Those questions aren’t about death as much as they’re about continuity. And the thing is, they’re the big items. There are others I’ve found myself asking: Where are the pink slips and title / registration for the cars? Where are the keys to the motorhome? Who comes to the house for cleaning, gardening, pool maintenance? What services need to be maintained? What’s the name of that property management company? Do you pay your bills online or over the phone? (yes, plenty of people still pay by phone).
In some instances, I’ve followed my mom around the house while taking a video on my phone just so I can have information recorded to check back on when needed in the future.
Plan for Incapacity Before You Plan for Inheritance
One of the most important reasons to have an estate plan is the possibility that you’re still very much alive, but temporarily or permanently unable to manage things yourself.
A financial power of attorney allows someone to act on another person’s behalf for financial matters according to the authority granted in the document. Healthcare decision-making is separate; a financial power of attorney doesn’t automatically give someone authority to make medical decisions.
Without that planning, a family may need court involvement to get authority to manage an incapacitated person’s property. Which is why the most useful question you can ask a parent isn’t:
Who gets your money?
It’s:
Who takes care of things if you can’t?
There may actually be several answers. The person you trust to make healthcare decisions may not be the person you want managing your investments. The person who is emotionally closest to you may not be particularly organized. One sibling may live nearby and another may understand the finances. One child may be excellent in a crisis but terrible with paperwork. There is no rule that says every role has to go to the same person.
The goal isn’t to hand out titles fairly. The goal is to build a plan that works.
Everything above is written from the adult-child seat, the one asking these questions of a parent. But this cuts both ways. Someday you’ll be the one naming a trustee, a healthcare proxy, an executor, for your own kids or whoever comes after you. The rules don’t change based on which chair you’re sitting in.
Loving Someone Doesn’t Make Them Right for the Job
Families often treat roles like trustee, executor, or power of attorney as if they’re honors.
“Of course I’ll name my oldest son.” “She’ll be offended if I don’t choose her.” “He’s my spouse. Obviously he’ll handle it.”
But these aren’t honorary titles. They. Are. Jobs. And depending on the circumstances, some of them can be really big jobs.
The CFPB describes four fundamental responsibilities for a financial fiduciary: act in the person’s best interest, manage their money and property carefully, keep their assets separate from your own, and maintain good records. In practice, that can mean bills, investments, insurance, property, taxes, all documented, while you’re grieving.
Think about this from the perspective of the person you’re naming. You aren’t just saying I trust you. You may be saying: someday, while you’re grieving me, I’d like you to manage a portfolio, maintain a house, deal with relatives, and keep records of all of it. That’s a very different proposition.
Which means we shouldn’t assign these jobs based on birth order, favoritism, or any bias other than whether the person can actually do the job. And you certainly should not assign someone the job without asking them and giving them context on the roles and responsibilities that come with it first.
And always, always name a backup.
Plan for the Family Dynamics You Actually Have, Not What You Wish You Had
We want estate plans to reflect an idealized version of our families. Everyone gets along. No one fights over money or struggles with spending. No one has complicated marriages or resentments. Everyone responds rationally to grief.
And then there’s your actual family. Good estate planning needs to be designed for that one.
Maybe one beneficiary shouldn’t receive a large inheritance outright. Maybe a trust should provide ongoing support instead. Maybe someone needs housing security more than a lump sum. Maybe a trustee should have discretion to pay certain expenses directly. Maybe one child is perfectly capable of inheriting assets outright while another needs guardrails. Maybe the family member who believes they should be in charge is precisely the person who shouldn’t be. Maybe someone is going to be angry about that.
Estate planning doesn’t eliminate family dynamics. Its job is to anticipate them.
Please Don’t Make Your Children Defend Your Decisions
If you make a call another family member may not like, own it while you’re alive. Don’t leave your executor to explain it, or one child saying, “This is what Mom, Dad, or Auntie wanted, I swear.” You don’t have to disclose dollar amounts. But there’s a difference between privacy and leaving behind a mystery.
Something as simple as, “I’ve chosen Jane as trustee because she’s suited to it. John will make healthcare decisions. I’ve talked to both of them and they’ve agreed,” means Jane never has to spend her grief convincing everyone she didn’t orchestrate the arrangement. Your documents speak for you. But whenever possible, so should you.
If the Assets Don’t Match the Documents, it’s a Problem
You can pay an attorney thousands of dollars for a beautiful estate plan and still fail to implement it. A trust may need to be funded. Property may need to be retitled. A plan isn’t complete simply because the legal documents are signed. Asset titling and beneficiary designations have to align with it too, which is why I don’t view estate planning as something that happens exclusively in an attorney’s office. The attorney drafts the structure. Someone still has to check the actual financial life underneath it, the house, the accounts, the insurance, the debt, against the story the documents tell.
And then there are the parts that were never really about money. Some people, like my grandma, start putting Post-it notes on things years in advance for who gets what. (That made holidays weird.) Who makes the healthcare decisions? What happens to the dog? Who gets the jewelry everyone thinks Grandma promised them? Estate planning sits at the intersection of law, money, relationships, mortality, and memory. Treating it as a transaction, we signed the trust, we’re done, misses most of what the planning is actually for.
Starting the Conversation With Your Parents
Back to the adult-child seat for a second, because this is usually where people get stuck.
You don’t need a 37-point checklist, and I wouldn’t start with “So, how much money do you have?”
Try: “I don’t need to know all the details of your finances. I just want to make sure that if something happened, we’d know what you wanted and how to help.” Then work outward: current documents, who has power of attorney, who makes healthcare decisions, whether those people know they’ve been named, where the originals are kept, who the attorney and CPA are. You don’t need every account balance. You need enough that a crisis doesn’t also become a scavenger hunt.
You may still get resistance. “You’ll figure it out.” “Everything is in the trust.” “I don’t want you knowing my finances.” That’s their right. But you can be clear about what you’re actually asking for. Not control. Just enough information to carry out the responsibility they may someday expect you to assume. There’s a real difference between “tell me how much I’m inheriting” and “if I’m the person you’ve named to handle this, I need to understand what that job involves.” The CFPB has an entire resource called Managing Someone Else’s Money for exactly this reason: an agent under a power of attorney or a trustee isn’t simply a helpful family member. They’re acting in a fiduciary capacity. If someone wants you to accept that responsibility someday, it’s reasonable to talk about it today.
The Transfer of Responsibility
I’m a CFP®. Of course I still believe in wills and trusts and powers of attorney and beneficiary reviews.
But I’ve come to see estate planning less as a stack of documents and more as a transfer of responsibility. At some point, someone else may have to pick up your financial life, temporarily or permanently, after you’re gone or while you’re still here. The question isn’t simply whether you’ve legally authorized them to do it. It’s whether you’ve made it possible for them to do it well.
There’s a difference between leaving someone an inheritance and leaving them a mess. There’s a difference between giving someone responsibility and giving them the tools to carry it. The best estate plans I’ve seen aren’t the most complicated. They’re the ones that leave fewer questions.
They tell the people you love:
Here’s what I want. Here’s who I’ve asked to help. Here’s where everything is. Here’s what you need to know.
And then, someday, when the people you love are already carrying grief, they don’t also have to carry the weight of figuring out what you meant.
Related: Financial Plans Should Evolve as Life Changes—Here’s How To Stay on Track