It’s Better to Be Safe Than Sorry

Bren Sheriff
Bren Sheriff

It’s Better to Be Safe Than Sorry

As we close out 2025 and look toward a new year, many families are taking stock of their financial and personal affairs. How about your family? Have y’all had The Talk? I certainly hope so, because some of you will discover that a little planning now can prevent tremendous pain later. Unfortunately, some folks don’t believe that fat meat is greasy and will only learn this truth after a crisis hits their family.

I have been in the financial services industry for more than a half century, and I have seen some things. This week I’m sharing some of the most common family disasters I’ve encountered while helping people “get their house in order.” The saddest part is that these disasters are so common, completely avoidable, and deeply destructive to family relationships.

Why You Need to Designate a Medical and Financial Power of Attorney

I provided life insurance to Mrs. Johnson for years and gently nudged her to set an appointment with me so we could meet with her family and create an estate plan. Even though she was well into her 80s, she always made excuses—but never made an appointment. When a sudden stroke left her unable to communicate, her three adult children assumed they could automatically step in. They quickly learned they could not: Mrs. Johnson had never signed the medical or financial power of attorney.

The hospital could not accept “family decisions,” and the children had no consensus on treatment. They had to petition the court for guardianship, a month’s-long process costing thousands of dollars. The court had to choose which child would serve as guardian. The two siblings who were not selected disagreed with the medical decisions made by their youngest sister, and the conflict became so intense that even at their mother’s funeral, the tension was visible. To my knowledge, they have never reconciled.

Lesson: A simple power of attorney, affordable and easy to complete—prevents a costly court battle and ensures you choose who handles your affairs.

First Wife Takes All

I provided both Mr. Williams and his second wife with life insurance for more than ten years and frequently reminded them to schedule an appointment to complete an estate plan. Sadly, Mr. Williams died suddenly at age 71, leaving behind his wife of 15 years.

Although he had listed his second wife on the life insurance policy he bought through me, he never updated the beneficiary on his retirement account. His ex-wife was still listed.

By law, the retirement funds went to the ex-spouse, not the current wife. The remainder of his estate had to go through probate because he had never created a will. What should have been straightforward became a long, painful, and expensive legal ordeal.

Lesson: Although I believe Mr. Williams intended for his retirement funds to support his current wife, he never completed the paperwork. Make sure all your documents reflect the beneficiaries you want.

A Tale of Two Sons

Mrs. Smith refinanced her home using my title company. During the closing she asked if she could add her son’s name to her title. We explained the process to her. A month later I went to her home, where her son also lived, to get them to sign the documents adding her son’s name to the title of the home.

When Mrs. Smith passed, the house was transferred entirely to the son on the title. Unfortunately, she had two sons. The son who inherited the house sold the house and did not share any of the proceeds with his brother - legally he didn’t have to. The younger brother ultimately walked away with nothing, convinced that his mother would have wanted the equity in her home to be shared equally by her sons.

Lesson: Joint tenancy seems simple, but it can create unequal inheritances. 

These families all had good intentions. They loved one another. They simply hoped everything would “work itself out.” But hope is not a plan. A little preparation today can protect your home, your savings, and your relationships tomorrow.

As we prepare for 2026, take an hour to review your documents: your trust, your powers of attorney, and your beneficiary forms. It’s better to be safe than sorry—and it may save your family from years of turmoil, heartaches, and severed relations.


My best to you and yours,

Bren Sheriff, CSA

P.S. I thank all of you that responded to last week’s survey.  It’s encouraging to know that the financial information shared here has been helpful.

THIS WEEK’S QUIZ : What key document allows a trusted person to make medical decisions for you if you become unable to speak for yourself?

Answer to last week’s quiz: The results of last week’s survey are in: People are more concerned about their financial well-being than they are about their physical health.

For Questions or Help: 773-817-0601 or basheriff1@gmail.com

Disclaimer: The illustrations presented in this column are not, nor are they intended to be, legal, financial, or any other licensed professional advice, you should contact the licensed professional of your choice for advice on your individual situation.

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