From Pets to Paintings: The Little Things That Can Cause Big Estate Trouble

Sentimental items might have little monetary value, but their disposition can cause hurt feelings. Help your family by talking about who wants what, labeling everything or sharing your possessions while you're still alive.

By Eric W. Bond

published 8 November 2025

in Features

An older couple smile while they sit on the porch and interact with their dog. — (Image credit: Getty Images)

Editor's note: This is part three of a four-part series about how to create and use your own Estate Planning Playbook. Part one introduced the concept and why it matters. Part two focused on the family love letter, a heartfelt guide to end-of-life preferences. In this article, we cover the often-overlooked details that can cause real stress if not addressed: family heirlooms, pet care and day-to-day bills.

When most people think of a will, they imagine a formal document that lays out how money, real estate and high-value possessions will be distributed after death.

While those financial assets are important, the biggest family disputes I see rarely center on a bank account or a piece of jewelry.

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The greatest tensions often arise over personal, sentimental items.

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These are things with little monetary value but deep emotional meaning. It might be the teacup Grandma always used, the painting that hung above the fireplace or the stand mixer pulled out every year for birthday cakes.

These items stir memories, and when they're not discussed or accounted for, they can create confusion and heartache.

When meaning matters more than money

Mike, a close friend, experienced this after his father passed away. Of everything his dad owned, all Mike wanted was the tool set they had used together on countless weekend projects.

That simple gesture would have meant the world to him as a lasting reminder of their time together.

Unfortunately, no one knew, and the tool set was given away before Mike could ask for it.

That story stays with me because I believe that if his father had known, it would have been a no-brainer to pass the tools on to Mike while he was still alive.

The takeaway is simple. Don't assume your family knows what matters to each other. Ask. Talk. Label. Share.

How to handle heirlooms without the drama

Too often, people wait until it's too late to have conversations about personal belongings. Those left behind are forced to make dozens, or sometimes hundreds, of small decisions about items they might not want or recognize their meaning.

Here are a few ways to make it easier for your family:

Have the conversation now. Hold a family meeting and ask which items mean something to your loved ones. You might be surprised by the answers. It's not always a diamond ring; often, it's the everyday objects full of memories.

Give items away now. If there is a mixing bowl you never use or a painting your daughter has always admired, consider passing it on now. You'll get the joy of seeing it appreciated, and it's one less decision for your executor.

Label key items. I've had clients use sticky notes behind framed artwork, under dishes or inside furniture drawers to indicate who should receive them. A simple "For Emma" or "Jack loved this" can go a long way toward preventing conflict.

Include a list in your playbook. One page labeled "Heirloom Instructions" in your estate planning playbook can save your family from confusion and distribute items as you intended.

Blended families and step-relatives can add complexity. Being clear and proactive helps reduce tension and shows your family that you've thought of everyone.

Don't forget about the dog (or cat)

An often-neglected piece of the estate planning puzzle is pet care. Dogs, cats and other animals are family members, but they can't speak for themselves when you're gone.

Make sure your estate planning playbook includes a simple pet directive that outlines:

Who you'd like to care for your pet(s)
Routines, medical needs or dietary notes
Contact information for your veterinarian
Emergency funds or pet insurance policies

This single page can make all the difference in ensuring your pet goes to a loving home and has proper care. It also relieves your family from having to make a rushed or emotionally difficult decision during an already stressful time.

Household bills and subscriptions: A hidden headache

One of the most underrated sources of confusion after someone passes is managing their monthly bills.

Today, many households have dozens of automatic payments from utility bills and insurance to streaming services and club memberships. Without clear direction, family members are left trying to decipher what's owed, what's recurring and which accounts are funding which bills.

Judy, a client of mine, handled this masterfully. In her estate planning playbook, she keeps:

Copies of every recurring bill
Notes on which bank account pays which bill
Account numbers, contact information and customer service details

Her rationale is simple. If something happened to her, she doesn't want her family spending hours on hold with the water company or struggling to identify which charges were still active.

Something many people don't consider: If a recurring bill continues after death, such as AAA, gym memberships, even a car loan, companies will often send a refund check in the deceased person's name. This creates even more paperwork for executors trying to deposit or cancel it.

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Having copies of bills is not just about transparency; it gives your family proof of where money is going and helps them close out accounts quickly and correctly.

It also avoids the headache of trying to persuade companies to issue refunds when you don't have documentation.

I've seen families spend hours trying to recover small amounts simply because they didn't have evidence of what had been paid and from where.

It's not about the money — it's about the meaning

It's rarely the most expensive items that cause the most stress. It's the small stuff — the irreplaceable, sentimental, personal touches that carry family meaning.

This part of estate planning is not about writing a check; it's about writing down what matters.

The best way to do that is to communicate. With a playbook, you don't just leave instructions. You leave clarity, comfort and confidence for your family.

In the final article of this series, we'll explore how to bring an Estate Planning Playbook to life by holding a family meeting, sharing your decisions and making sure everything is up to date and accessible.

Creating a plan is just the first step. Putting it into action is where the real impact happens.

Disclaimer

This article was written by and presents the views of our contributing adviser, not the Kiplinger editorial staff. You can check adviser records with the SEC or with FINRA.

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Eric is a prominent figure in the Long Beach community, where he has made significant contributions both professionally and philanthropically. As the President and Founder of Octave Wealth Management, Eric has steered his financial planning practice to new heights since its rebranding and expansion in 2024. His career, which began in 1997, has been marked by a steadfast dedication to excellence, reflected in the success and growth of his practice.