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On August 13, 2025, my husband and I found my sister unresponsive in her home.
The moment was traumatic and terribly upsetting. My thoughts immediately turned
to my mother, how would I tell her she had lost her daughter while dealing with
her son’s terminal cancer diagnosis?
That was the personal side of loss. Days, weeks and months later came the
business side of dying.
My sister, Victoria, Tory to everyone who knew her, lived a full and colorful life.
She worked in healthcare, built close friendships, loved staying active, and filled
her home with warmth and personality. More than anything, she cared deeply about
the people in her life. Relationships mattered to her, and she made time for them.
With Jonathan’s urging, she knew she needed a will. She had taken that step, she
wrote one. My brothers and I even had copies. She believed she had handled things.
But after her death, we couldn’t find the original. And as we looked closer, we
realized something worse: the document wasn’t legally binding. It had not been
prepared by a lawyer. It lacked notarization and key legal language. It expressed her wishes, but legally, it didn’t carry weight.
Because Tory had no spouse or children, my 86 year old mother was considered
next of kin. She had just lost her daughter and was also coping with a son battling
cancer. Taking on the role of executor wasn’t realistic. Our lawyer ultimately
appointed me as personal representative.
That’s when the complications began.
Without a valid will, everything moved through the courts. Even selling her house
required judicial approval. Before submitting a contract, we needed an appraisal
based on the value at the time of death, then another based on current market value.
The judge had to approve the sales price. What normally might be a 30 day closing
became 45 days or more.
Every step took time.
Every delay added stress.
And all of it unfolded while we were grieving.
The irony is that Tory tried to do the right thing. She didn’t ignore estate planning.
She made an effort. But a will that isn’t legally valid can create nearly as much
complexity as having no will at all.
That’s the lesson I didn’t fully appreciate before this.
Estate planning isn’t just about writing down your wishes. It’s about making sure
those wishes are enforceable. The difference between a properly executed will and
an informal document can mean the difference between a smooth process and
months of legal oversight.
It can affect who is in charge, how quickly assets are distributed, whether court
approval is required, how the property is sold, and how much stress falls on family
members.
None of this changes the grief. But it can greatly change the burden placed on
those left behind.
Tory lived with warmth and generosity. She cared deeply about family and friends,
and she tried to plan ahead. But good intentions weren’t enough in this case.
If there’s one takeaway from my sister’s passing, it’s this: Don’t assume a will is
valid just because it exists. Make sure it’s properly executed. Make sure it meets
your state’s requirements. Make sure someone knows where the original is kept.
Because the goal of estate planning isn’t just to state your wishes. It’s to make
things easier for the people you love.
My sister left us with memories, love, and one final lesson.
A will should bring clarity, not questions.
Andrew, my condolences. I’m familiar with this process and the turmoil that can occur. I wrote this HD article summarizing my experiences.
That’s a lot to go through. Seeing a loved one in that state. And perhaps even worse, sharing with a mother that she survived her own daughter. All this in the context of Jonathan’s struggles. What you have been through of late! My condolences.
15 years ago, I gritted my teeth while my wife and I spent several thousand dollars getting an estate plan done with a law firm that specialized in them. I am highly confident, knowing the owner of the firm, that all is buttoned down.
I don’t even think anymore about the money we spent to get it done, only that my son and daughter hopefully will not have to worry about that part of their mom and dad passing on.
There are many things we can do to make our departures easier for those we leave behind. Making sure these affairs are taken care of is near the top, if not at the top.I realize that not everyone needs or wants an estate plan; for my wife and me, it was the way to go, however.
John,
My mother in law died at 103 years old last March which was the month following the passing of the first born child. I don’t think it was an accident as my mother in law was actually very healthy. As a matter of fact they performed an ultrasound of her heart the day before she passed and her function was completely normal.
IMO, the best will is the one in your attorney’s fireproof safe….just as long as your next of kin knows who your attorney is.
Deepest condolences on your losses, Andrew. It’s amazing, isn’t it, how these tragedies come in clusters?
And my I offer strongest endorsements of your warnings. My story is not dissimilar to yours. Please forgive the length, but I think it’s illustrative.
My dad kept a metal box on the top shelf of the linen closet in our family home near Chicago, where he now lived with his girlfriend. The box contained his will and the house and car titles and every other document that his passing would require. And every time I came home from wherever I was living around the country doing TV news, we did a quick review of the box.
On July 2, 1993, two days after my dad and his girlfriend had come out to visit me in Rhode Island (we had stuffed ourselves at the Lobster Festival), she called me to tell me he had died suddenly, shockingly, at 58.
I was on a plane to Chicago the next morning, and she and I walked into the bathroom together to get the box down from the shelf.
It was empty. Empty.
They’d been planning a trip to Arizona, and as best I could guess in later years, he’d been planning to surprise her with a marital side trip to Vegas. I still assume that to keep it a complete surprise, he had taken all the papers to some lawyer to change his will, add her name to the house title and bank accounts etc. without telling her. We tore his home office apart but never found the name of a lawyer or any indication of where all the documents were.
So legally he had died intestate.
What followed was six months of probate hell. I dealt with two lawyers, an accountant, various city and county legal authorities, a judge, and two acidic siblings who didn’t trust me to give them their fair share — as well as the onerous realty process Andrew describes in his article. All at a distance of a thousand miles while the girlfriend stayed in the house to keep it safe.
Even when I could sell the house, it sat on the market for weeks. I finally sold it in the middle of producing the 5:30 newscast at WJAR-TV in Providence. My dad’s girlfriend’s realtor called me on the studio phone at 5:35 with the buyers in the house. Between news stories and giving directions to the live reporters, I negotiated with the buyers, and by the end of the weather segment, we had a deal.
The remaining financial processes in probate were still to be completed, but nine months after his death, I finally had my dad’s slender estate money distributed, all the debts paid off, and my dad’s car towing a U-Haul full of his furniture to California… where I started a new life with it.
Thank you for sharing Mike. It just shows you never know when your time is up so it stresses the importance even more to plan your estate now.
Andrew,
Unfortunately I have experienced the passing of multiple family members within a short time of each other so I know how painful it can be. In 2017 I lost my twin brother (59), then both my parents within four months of each other a year later. Last year I lost my sister in law, mother in law, and an uncle within a few months of each other.
After my parents passed we set up a trust for our estate so our children would not have to undergo the stress of probate like my sister did. It was expensive but making things simpler for our children made it worth every penny.
Thank you David for your comment, you have been through a lot and I am so sorry. Words will never suffice such losses.
Andrew, thanks for this important message.
So sorry to hear that your family suffered so much. Well done for you efforts to bear this load.
Thank you Greg, I am hoping 2026 will continue to the year to reset and move forward. Jonathan and Tory will never be forgotten and they will always have a place in my heart.
Selling my business last year, combined with having a very organised wife, was the spark that got us to finally redo our estate documents. It’s not the most pleasant task to undertake, but as your experience highlights, it’s a hugely important one. The unexpected bonus — the snowball effect, if you like — was that when we sat down with my wife’s sister and brother-in-law to ask them to be our executors, it created the momentum for them to sort out their own will. Two birds with one stone.
Thank you Mark, a will is so important at any age because the next day is never promised to anyone.
Andrew,
Thanks for sharing what must be a difficult story to tell. The last email response I received from Jonathan was 4 days after your sister died. At the time it felt so unfair, and it still does. Thanks for taking care of your Mom, your brother, and your sister’s affairs. Clearly empathy, caring, and bravery run strong in your family.
Thank you Rick for your caring words. It has been a difficult time for our family but there are lessons to be learned that I feel may benefit the readers of HumbleDollar. I tell it how it is.
Oh, Andrew, I’m thinking how hard that period must have been for you and your family, especially your mother.
Thank you for this reminder to keep wills updated, along with letters to explain important things. Jonathan’s diagnosis prompted us to review beneficiaries (either payable on death, or transfer on death) for all of our financial accounts, and even our house, (Ohio allows this, some states do not).
Sounds like you have it all planned out. Unfortunately when you are young you don’t think you need to plan ahead. My sister died at 57, she thought she had a good plan but sadly not.