Today is my mock death day. No, I’m not joking.

This is normally an annual tradition—which I’ve now practiced for almost two decades—is one of the most important, thoughtful, and oddly comforting things I do for my family, my business partners, and even myself. I call it my greatest act of kindness.

It’s been two years since my last dry run, and as usual, so much has changed.

We welcomed our tenth grandchild this year—ten! Our businesses continue to grow and evolve, especially in response to the AI-driven industrial shift that’s reshaping construction and real estate. The size and complexity of our holdings, projects, partnerships, and obligations have multiplied. Yet, somehow, I still find myself nearly alone in obsessing over what exactly would happen if I were to die today.

Now, for the record, I don’t plan on dying anytime soon. I take care of myself, I plan to live a long life, and frankly, I love what I do too much to slow down. But I also travel more than almost anyone I know, often to remote locations, and I’m an active adventurer. Two years ago, in September, I took an unexpected slide down the side of a mountain. It could have ended very differently. [Read that story here]

This year, I “ mocked death” on safari in Africa. Symbolically, of course. But the location matters, because logistics matter. My longtime Chief of Staff—who retired this year but graciously agreed to remain my emergency contact—knows exactly what to do. If I were to die while abroad, she holds the responsibility to make critical, time-sensitive decisions. Do we repatriate my body for burial, or—if local laws or costs become a burden—opt for cremation and return ashes to Saint Louis? (Let’s be practical: a heavy casket is not a carry-on.)

There’s no glamour in death, but there can be clarity. That’s what the mock death offers. Clarity.

The Complexity of My Departure

When the real moment comes—and eventually, it will—it won’t be simple. I’m the Executive Chairman of one of the largest construction firms in the U.S., with real estate development, fund management, multiple foundations, and hundreds of business partners and investors across countless special purpose entities. That alone would be complicated enough. But add in extended family, philanthropic trusts, and cross-border considerations, and the list of posthumous decisions quickly becomes a labyrinth.

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My late wife, Ellen—my childhood sweetheart and partner for 25 years—passed away in 2010. Her presence still shapes my life. Her trust remains an active part of our family’s financial and charitable landscape. I often say she’s here with us in spirit and in structure. Her legacy was built to last.

As the years go by, I’ve realized how critical it is that the people I love and trust know exactly what to do when the time comes. Because the truth is: when death hits, people are grieving, vulnerable, emotional. It’s not the right moment to untangle complex decisions. That’s why we do it now—yearly—before it’s real.

The Three People Who Hold the Keys

There are three core people involved in the first 24 hours after I “depart.”

1. My former Chief of Staff is responsible for notifying the family and bringing them together as quickly as possible. She pulls the plug, coordinates travel, logistics, and ensures everyone is in one place. She also notifies close friends, offering them the chance to gather in a few weeks for a proper celebration of life—one filled with good food, great stories, and probably a few stiff drinks.
2. My General Counsel and CFO step in to activate the legal and financial protocols. They notify trustees, shareholders, and business partners. They coordinate with my estate attorney and ensure continuity across our operations. Meanwhile, my family office triggers the insurance notifications and navigates regulatory requirements to ensure no disruption or delay.
3. My Director of Executive Operations handles public communications. The obituary (which is updated as of today), burial arrangements, family and partner travel and our media response which all need to be managed swiftly. I’m to be buried within 24 hours, with no funeral or wake—unless my body can’t be accessed quickly, in which case plans adjust. We’ve covered it all.

Everything must be fast, clear, and coordinated. Because when I do go, I don’t want chaos. I want peace—for those I leave behind.

Why the Mock Death Matters

After every mock death, we sit down—my whole family—and walk through everything. We look at the waterfall of decisions, review the structure of bequests, insurance proceeds, and business transitions. Everyone has a clear picture of what’s coming, what they’re responsible for, and what they’re entitled to. No surprises. No infighting. No guesswork.

Many friends who’ve heard about my mock death practice say it’s brilliant, even inspiring. But I’ve yet to hear of anyone doing it themselves. Maybe because it feels morbid, or maybe because it’s too emotionally real. But I’d argue: what’s more real than giving your loved one’s peace of mind?

A Final Thought

When the Grim Reaper finally comes calling, I’ll have done my best to make his job boring and uneventful—for everyone else. That, to me, is an act of love.

So if this post makes you uncomfortable, I understand. But I also hope it inspires you. Take care of the bad news before it happens. You won’t regret it—and your family will thank you.