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Five Lessons I Learned As An Executor

Recently, I had the unfortunate experience of being an executor for my grandmother’s estate. When I agreed to do it, I never could have imagined what was in store.

There was no amount of financial planning experience, seminars, blog posts, books, etc., that could have prepared me for the task that I was faced with.

The good news for you is that I learned quite a few lessons in the process, and I want to share them with you, though I am by no means an estate attorney.

It is my hope that the challenges I faced can be avoided for you if you have the honor and curse of being someone’s executor, and that you will be able to make life easier for the person who will act as your executor one day.

Lesson One: Make Your Wishes Clear

When my grandmother was alive my family spent a lot of time with her. We would travel down to her house in Winchester and stay for the weekend. We would sit in her living room (or when it was night on the back porch), and talk about everything under the sun.

Pretty much the only thing we never talked about was her estate after she passed.

Logically, I know that wasn’t necessarily wise, but it’s just such an awkward conversation. I couldn’t stand the thought of not being able to spend time with her, seeing the joy on her face as she played with my kids, buying her breakfast in the morning that she would never eat, and listening to all the crazy stories she would tell about what happened since the last time we came to visit.

I just kept telling myself we would talk about it next time.

To make a long story short, she was admitted to the hospital with double pneumonia and passed away a few days later. Luckily, I was able to say my goodbyes, but I never had the chance to find out some important details concerning her estate.

Just like that, I was in charge of administering her estate and I didn’t know where to begin.

There were so many unanswered questions…

Like where are her important documents, what bank does she use, who did she want her pallbearers to be, where did she want her service, did she have a mortgage, is there any debt that needs to be taken care of, who should be invited to the funeral? The list goes on and on.

The pieces to the puzzle finally did get put together, but it was incredibly painstaking and I had to deal with it all at a time when all I wanted to do was grieve.

All of this could have been avoided if I had just cowboyed up and had the awkward conversation with her to find out.

Don’t make this mistake.

If you know you are going to be an executor of someone’s estate one day, please do yourself a favor and have that conversation with them as soon as possible.

Even if you’re not an executor, and never will be, you are going to pass away one day (as shocking as that may be for some). Take the lead and have this conversation with the people who will be responsible for your estate when that day eventually comes. They may be resistant, but trust me, they will be grateful one day.

Lesson Two: Set Aside Money for Final Expenses.

The other thing I never really considered was who was going to pay for everything.

I know, shame on me for being a financial advisor and not thinking about the financial consequences of someone passing, but cut me a little slack. It’s much easier to talk about people’s finances when they are not your family members.

Someone has to cover all the costs

It turned out that there was nothing set aside at all, and when all was said and done my dad and I had to come up with over $15,000 out of pocket to cover the funeral, estate taxes, attorneys, etc. It wasn’t pretty and we weren’t fully prepared for it.

It would have been much better if she had set aside a bank account, purchased a final expense life insurance policy, or if that wasn’t an option my dad and I should have funded one ourselves. Anything would have been better than a $15,000 surprise bill.

Lesson Three: Consider a Living Trust.

Fortunately, my grandmother did have a will in place, which helped tremendously. However, she did not have a living trust.

Having one would have made the whole process much easier. My grandfather passed away over 10 years before her, so when she passed away no one owned any of her property.

The problem

That meant everything had to go through the court, in a process called probate. It’s long and tedious and can present challenges.

For example, the contract she had on her reverse mortgage stated that the house had to be sold within six months.

The problem with that was that it took almost six months to get everything settled with the court so that we could even put it on the market!

The bank didn’t care, and informed us that they were going to foreclose on the house. Luckily for us, the estate was insolvent so we told them to go ahead. For our situation this was actually easier, but if the circumstances were different it could have been really bad.

The potential solution

If she had a living trust, most or all of this probably would have been avoided.

The thing to understand about trusts is that they have tax identification numbers and are considered legal entities. Unlike living, breathing entities however, trusts never die.

If she had a living trust, the ownership of all of her assets could have been transferred to it so that we could handle the distribution immediately without going through the probate process.


It’s important to note that I am not an estate attorney and before making any legal decisions about your estate it is highly recommended that you consult with an attorney who specializes in estate planning.

Lesson Four: Be Well Organized.

The other challenge I ran into was trying to figure out where everything was.

For example:

  1. What accounts needed to be closed?
  2. Did she have any insurance policies?
  3. Did she have any investments?
  4. Did anyone owe her money?
  5. Did she owe anyone money?
  6. Did she have any online accounts? If so, what were the passwords?
  7. Did she have a safety deposit box?
  8. Did she have anything in storage?

These are things you just don’t talk about during the course of regular conversation, and questions you don’t really think to ask.

It would have saved probably 20 hours of my time if she had the answers to all of these questions organized in one place.

Lesson Five: If You Don’t Know, Ask for Help.

The last important lesson I want to share with you illustrates the power of how even small financial decisions with good intentions can have a big impact on your overall financial picture.

The bottom line is that my grandmother knew almost nothing about finances and had too much pride to ask for help. Soon after my grandfather passed, she took out a home equity line of credit on her house that was paid off at the time to lend to her sister.

A few short months later, her sister paid back every cent. But rather than cutting a check to my grandmother she thought it would be best to pay it back to the mortgage company directly. Her intentions were good and on the surface it would seem like she was doing the right thing.

While her intentions were good this was a huge mistake

Unfortunately, in my grandmother’s case, this was most likely the beginning of what would be her financial ruin. You see, she was living on a very fixed income and had made it a habit to extend her generosity to anyone who asked. That’s just how she was.

With her limited knowledge and the bulk of her income tied up in the equity in her home, she felt a reverse mortgage was the best way for her to generate enough income to pay her bills.

On her own she entered into a terrible contract with the mortgage company that ended up costing her everything she had.

Could this have been avoided if she sought professional guidance?

If she had consulted with a financial advisor, they may have been able to help her understand all of the options she didn’t even know were available to her.

Obviously, everyone’s situation is different, and no one knows how things would have turned out if she had done things differently. But it stands to reason that if you are not confident in your ability in any subject, no matter what that subject is, chances are there is someone out there that may be able to show you a much better way of doing things.

So when it comes to your estate, your finances, and the people that you care about, please consider getting the right people on your team that can guide you toward making informed decisions about your future.


I hope this post will help you begin to put some thought into the important actions that you need to take as soon as possible when it comes to planning your estate.

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At Medallion Financial Group, we believe financial planning is about Family. We have been helping families invest in the future since 1987 through a holistic planning approach. We recognize there are a variety of needs when it comes to retirement planning, plan rollovers, annuities, college planning, life insurance options, and investment management. It is easy to get lost in a sea of choices. Our financial advisors help with the basics and beyond to enable our clients to get the education, advice and management they need to retire with confidence.

Our focus is twofold: first and foremost, we are fiduciary advisors. We stand against any violation of laws, values, and ethics. Second, we treat our clients as part of our family, not only those who call Maryland and Georgia home, but clients across the US who have benefited from our reputation of personal service, integrity, and expertise.

We strive to exceed client’s expectations – because we have high expectations of ourselves.

post icon in Retirement by Medallion Group Mar 18, 2020