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This year it’s December 18, 2023.

My belief is the single greatest act of kindness I can accomplish is to have an incredibly detailed written process ready to go in the event of my untimely death.

Yes, it’s kind of morbid, and difficult to think through, yet I’ve been doing it for 15 years ― every single year in either November or December ― after which it’s randomly announced to my team close to the day of my supposed demise.

My death would be unusually complicated in comparison with most people’s. I’m the Executive Chairman at one of the largest construction companies in the United States, and we also operate a real estate development business with fund management, multiple special purpose entities and hundreds of partners. There are also multiple foundations and charitable commitments to consider, as well as an extended family with four married children, nine grandchildren and one on the way. Friends and legacy partners and my late wife Ellen’s family and Jane’s family are high on the list of my responsibilities. I’m still engaged in multiple outside organizations as well, although I’ve stepped back from a good number of outside interests to focus on my personal foundation for a while.

Ellen may no longer be with us physically, but she remains with us in spirit. We met in junior high school and a lot of people know that the first time I saw her I decided I was going to marry her. It wasn’t as simple as that, but we did in fact get married when we were 25 years old and were married for 25 years before she passed to the heavens from a genetic disease. She was an amazing human being, and is still remembered very fondly by everyone who knew her.

The idea of a mock death first occurred to me a couple of years after Ellen was diagnosed with a terminal genetic disease. Two years after that I concluded that we already had a pretty complicated estate, and we didn’t have a very good plan. We decided to create a scenario where I died, just to see where all the chips would fall. I didn’t like what I learned and where I saw the chips rolling and sliding off the table.

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Since then, I’ve completed this exercise every year and sleep better and feel like a kinder human being as a result. At the same time, I’ve had many friends who, sadly, have passed away during that time frame. My CFO was hit and killed by a car while training for a marathon before the Great Recession, and it turned out he had an unsigned estate plan sitting toward the back of his desk. Another of my partners, a CPA by training, also died without a plan and with his family unaware of the complexity of his estate. I have many friends whose spouses don’t know where the important papers are, are in the dark about where the money comes from or how it goes out, and don’t even know how to pay their own bills at home.

I suspect the vast majority of people who have accumulated any kind of wealth at all don’t actually really know what can happen when they pass away. They may have a last will and testament, and a living will and some life insurance, and they think their friends and family will figure out how to take care of all the bits and pieces. When a good friend passed away recently, it took four days for the family to pull together an obituary. These things can be complicated. For example, no one wants to leave an important family member out of an obituary, and getting it right is important. But doing it during a situation as traumatic as a loved one’s death is really difficult.

A ton of friends who are aware of my mock death exercise every year tell me it’s amazing and thoughtful, and that they realize how important it is. However, I don’t know any of them who have brought themselves to pull the trigger on their own mock death.

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When the Grim Reaper comes to get me, there are three key people that are responsible for the notifications. Here’s what happens:

My General Counsel and CFO at Clayco takes care of the legalities and composes the list of trustees, shareholders and business partners who need to be notified, along with my estate attorney. This person also reaches out to my family office and begins notifying the insurance companies and ensures that all of the formalities, rules, and regulations are followed exactly so as not to disrupt any part of that process.

My Chief of Staff (and close friend) is responsible for notifying the family and bringing them together as quickly as physically possible to one location, which involves taking care of their air travel, and so forth. She also notifies close friends and gives them a heads up that in a few weeks, if everyone wants to, there will be a celebration with plenty of drinking, good food, and stories, for those who’d like to speak...

My third close associate is responsible for the obituary (updated regularly), the burial arrangements, and working closely with the company's press to make sure the message gets out properly and in a timely manner. Everything must happen quickly because I’m to be buried within 24 hours of my death, assuming my body is easily accessible. LOL, there is a good chance it won’t be easy! There will be no wake or funeral because these are a bummer.

It’s important to me that right after the mock death the entire family gets together to go through the waterfall events and processes, so that there are no surprises when it actually happens. We have openly discussed insurance proceeds, stock transfers, bequests and other critical information that everybody should know in advance, so there is nothing unexpected and no arguments. Jane can rest assured that she shouldn’t have any questions, there’ll be no confusion, and that she can sleep at night knowing that if something happens to me, she’ll be just fine.

An important fact, and one of the reasons I’m writing this and being so open is that it’s shocking how many changes we have to make every year based on the reality of the business and simply how life changes from year to year. Laws change, tax rules change. I leave partnerships and enter into new ones, start new investments, and add new art pieces to the collection. It’s safe to say this mock death exercise would turn up a lot of surprises for most people, but doing it gives you time to make the changes that will have positive impacts on your friends and family.

I hope this morbid post inspires people to take care of, or hopefully lessen, the bad news before it happens.

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