Most of us avoid thinking about what happens after we die.

It is uncomfortable, emotional, and easy to put off for another day. But when we avoid these conversations, we often leave behind more than grief. We leave behind confusion, resentment, and in some cases, years of legal battles.

That is what certified executor advisor David Edey learned the hard way. And it is why he now dedicates his work to helping families plan better.

What Is an Executor and Why Does It Matter?

An executor is the person you appoint to carry out your wishes after you die. This includes paying off debts, distributing assets, closing accounts, filing taxes, and dealing with beneficiaries.

Think of the executor as the project manager of your estate. They are responsible for guiding everything to completion while also navigating their own grief.

According to David, the job involves more than 150 tasks and can take an average of 100 hours or more. Without preparation, it can quickly spiral into a nightmare.

A Personal Story of What Happens Without a Plan

After losing both of his parents to cancer within a year, David was named one of three executors. But there had been no conversations about the details of their estate. No clear expectations. No guidance.

What followed was seven years of court appearances, ten trips to court, and over $50,000 in legal fees. The emotional toll was just as costly.

This experience pushed David to write his book Executor Help and create resources for others to avoid the same pain.

Most People Choose the Wrong Executor

Many people choose an executor based on familiarity rather than ability. They may pick their oldest child, a close friend, or a relative without ever asking them or explaining the role.

That is a mistake.

An executor should be someone who is emotionally mature, organized, and capable of making decisions under pressure. They must also be ready to communicate with family members and professionals like lawyers, accountants, and financial advisors.

And yes, they should be asked ahead of time.

Avoiding the “Family Mess” by Being Proactive

Families are complex. Even close siblings can clash when grief and money enter the picture.

David says there are three types of families:

1. Families who believe talking about death will make it happen, so they avoid it.
   

2. Families who say “we’re fine” because a will exists but never discuss what is in it.
   

3. Families who have the difficult conversations ahead of time and create peace for those left behind.
   
   

The last group is rare, but it is the one we should all strive to be part of.

Wills Are Not Set and Forget

Just having a will is not enough. David emphasizes the importance of keeping your documents updated as your life changes.

Some examples of when to review your will:

• After a marriage or divorce
  

• After having children or grandchildren
  

• After losing a loved one
  

• If your chosen executor becomes too old or ill
  

• If you give a large gift during your lifetime that should be accounted for in your estate
  
  

Think of your will as a living document that needs attention every few years, or whenever something major changes.

What If You Do Not Have Family to Name as Executor?

For people without traditional family structures, it can be even harder to make these decisions.

David recommends working with a professional executor, trust company, or bank. While these may charge a fee, they bring experience and neutrality to the process.

He also encourages thinking about legacy. If there are no close family members to name as beneficiaries, consider directing your estate to causes that matter to you—such as education, climate change, animal rights, or healthcare.

How to Start the Conversation

It is hard to know when to bring up these topics with loved ones. The holidays often feel like the only time the family is together, yet it can seem too heavy for that setting.

David suggests a gentle approach.

You can say something like, “I was listening to a podcast that got me thinking, and I recently updated my will. I realized we haven’t talked about any of this as a family. Can we set a time to go over it together?”

You might also bring up a celebrity estate planning failure as an icebreaker. Use their story as a springboard into your own conversation.

Three Tips for Choosing an Executor

1. Choose based on ability, not obligation.
   Do not assign the job to someone just because of birth order or tradition. Pick the person who can handle stress, logistics, and communication.
   

2. Talk to them in advance.
   No one wants to be surprised with this responsibility. Ask them if they are willing, and explain what the role involves.
   

3. Set them up for success.
   Provide clear instructions, up-to-date documents, and access to important contacts. The less they have to guess, the more peaceful the process will be for everyone involved.
   
   

The Greatest Gift Is a Plan

End of life planning is not about being morbid. It is about being responsible.

It is also about love.

As David says, the greatest gift you can give your family is a plan. It gives them space to grieve without chaos. It gives them clarity instead of confusion. And it helps ensure that your final wishes are respected and fulfilled.

You do not have to figure it all out at once. Just take the first step.

🎧 Watch the full conversation between David Edey and Niki Weiss on The Digital Legacy Podcast

Take the Next Step: Start Planning with My Final Playbook