A few years ago, my daughter Amanda served as executor of her grandmother’s estate. Her grandmother had a will, but she had done little to prepare for what would happen after she died. For several months, Amanda struggled to find assets, accounts, passwords, documents, and all the other information necessary to administer the estate.

We talked often during those months. I heard about the frustrations and the unnecessary detective work. Amanda is also the named executor of my estate, and one day, after dealing with yet another frustration, she looked at me and said:

If you leave a mess like this for me to deal with, I’ll kill you!

We both knew she was kidding. But I also knew she was making a serious point, and I took it seriously.

A Will Isn’t Enough

Most of us know we should have a will. Depending on our circumstances, we may also need living trusts, other trusts, powers of attorney, healthcare directives, beneficiary designations, and other documents. Those things matter and getting them right requires thought and the assistance of qualified attorneys and other advisers.

But Amanda’s experience taught me something else. Having an estate plan and leaving an estate that can actually be administered are two different things. A will may say what should happen to your assets. It doesn’t necessarily tell your executor what those assets are, where they are, how to find them, or whom to call with questions.

There is another issue that may be just as important. If we don’t communicate what we want to happen, we leave a vacuum. Children and other beneficiaries may begin filling in the blanks themselves. Why did Dad do this? What did Mom intend? Is this really what she wanted?

Where intentions are appropriately explained beforehand, conversations can prevent misunderstandings later. Silence leaves room for people to create their own explanations, and those explanations may be very different from what we intended. A good estate plan can distribute assets. Clear communication can sometimes prevent the distribution of misunderstandings along with them.

As an aside, the concept of deciding what shareholders want is similarly important for businesses. I have written and spoken about buy-sell agreements for more than twenty years.  I often say that business owners need to agree on the defining elements of their buy-sell agreements while everyone is alive and healthy.  Reaching agreement may not be easy in the here and now, but it will be virtually impossible when an owner is in the hereafter.

The same is true for our wills and estate planning.  When one is in the hereafter, his or her existing will and planning will define the experience to be had by remaining family members and other gifts or provisions that one might desire to make.

When Several Kinds of Planning Collide

As we pass through the sixties and later of life, several things begin to converge. We may be retiring, semi-retiring, working differently, or figuring out what to do with our days. We need to think realistically about what it will cost to live for however many years remain. We may want to simplify our finances. And we need to decide what should happen to whatever remains when we are gone.

We all know that we will die someday.  Hopefully that will be a day far into the future for you and me.  But the prospect of death isn’t particularly pleasant to contemplate. It is very easy to procrastinate, but that is not good for you or me, and it is certainly not good for our families.

I’ve discovered that preparing for death and dwelling on death are very different things. There is considerable satisfaction in knowing that things are in order.

My attorney gave me a form designed specifically to create a roadmap—assets, accounts, passwords, important contacts, and other information that someone administering an estate might need. Completing something like that takes time and keeping it current requires some discipline. But imagine the alternative: your executor sitting at a desk someday trying to reconstruct your financial life from whatever he or she can find.

Could Someone Step into Your Shoes?

I’m certainly not an estate-planning attorney, so this is not intended to be an estate-planning checklist. But Amanda’s experience and my own preparations suggest some questions worth considering:

1. Who will be responsible when I can’t be? Have I talked with that person about the responsibility?
2. Are my legal documents current? Do they still reflect my family situation, assets, circumstances, and wishes?
3. Could someone identify what I own and find it? That includes bank and investment accounts, retirement assets, real estate, business interests, insurance policies, valuable personal property, and other assets.
4. Could they gain access to my digital life? Passwords, devices, email, online financial accounts, cloud storage, and other digital assets increasingly matter.
5. Would they know whom to call? Attorney, accountant, investment adviser, insurance professional, business associates, and others who can help. With emails and other contact information.
6. Have I communicated my intentions? Where explanation is appropriate, do the people involved understand what I (or you) want to happen and why?
7. Am I leaving unnecessary complexity behind? Old accounts, obsolete documents, scattered records, and years of accumulated financial clutter can all become someone else’s problem.
8. Finally, when did I last review all of this? Getting things in order is not a one-time event. Life changes. Families change. Assets change. Our wishes can change, too.

My work in the estate tax valuation area over many years has revealed estates where one or more of these questions were not timely addressed.  Things can get messy.

Not Everything We Leave Is an Asset

For Christmas in 2023, my children gave me a booklet called Papa, Tell Me Your Story. I took them seriously. Similar books are available on Amazon.com, at bookstores, and elsewhere for Moms, Grandparents, and more.  You can write your responses in the books.  In my case, I extracted the questions and typed my answers.  Consider getting one. Or maybe get books for your parents or grandparents.

By Christmas of 2024, I had written a 34-page “opener,” and they loved it. Thinking about this post reminds me that I have more work to do. Christmas 2026 is a good goal.

That book won’t be listed on an estate inventory and doesn’t need a beneficiary designation. But someday it may be worth more to my children and grandchildren than some of the things that will be listed.

The process outlined here is part of getting our affairs in order. We spend much of our lives accumulating things – assets, experiences, relationships, stories, lessons, and memories. At some point, stewardship begins to mean not only accumulating and managing but also deciding what should happen to them and what we want to leave behind.

Estate planning forces us to think about our death. Estate readiness asks us to think about the people who will still be here when we are gone. That’s a somewhat different perspective, and for me, a more useful one.

Amanda’s warning still makes me laugh. And I’m trying very hard not to leave her a reason to carry it out.

As always, be well, and age gratefully,

Chris

PS  If you enjoy this post and the blog, consider telling your friends and share with your social media.  If you like it, they will probably like it, too.