What the Kentucky Derby can teach every one of us about estate planning

Published 6:07 pm Thursday, May 8, 2025

Each May, the Kentucky Derby captures the attention of horse racing fans, fashionistas and the American elite. 

For many of the wealthy patrons who attend, it’s not just a two-minute race — it’s a months-long production. Attending the Derby, especially from Millionaire’s Row or a private box at Churchill Downs, involves high-stakes planning: couture outfits, extravagant travel arrangements, top-shelf hospitality and meticulous attention to every tiny detail.

Wealthy Derby-goers often commission custom hats that can cost thousands of dollars. They hire stylists to match their designer suits and dresses to the season’s fashion theme. Private jets are booked months in advance. Luxury lodgings, exclusive parties, and tailored Derby experiences can collectively cost more than a new car — or even a modest home.

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For the ultra-wealthy, the Derby isn’t just a sporting event. It’s a statement. It’s a lifestyle ritual that requires strategic planning and flawless execution.

But while Derby attendance is a privilege reserved for a wealthy few, there’s another kind of preparation that’s just as involved and significantly more impactful for the average person — estate planning. And unlike Derby tickets, estate planning isn’t a luxury. It’s a necessity.

The common ground: strategic planning

What do Kentucky Derby preparations and estate planning have in common? A lot more than you’d think.

Both require:

Advance planning: Just as you can’t snag a Millionaire’s Row seat last-minute, you can’t create a meaningful estate plan in a day.

Professional guidance: Derby-goers hire stylists, travel consultants and hospitality experts. Estate planning demands attorneys, financial advisors and sometimes tax specialists.

Attention to detail: The fit of a hat matters at the Derby; the wording in your will matters just as much — if not more — in court.

Personalization: Every Derby experience is unique. The same is true of an estate plan. Your goals, your assets, your family dynamics – they all require custom attention.

The irony is that while the Derby’s glitz garners headlines and Instagram photos, estate planning — though far less flashy — has real, lasting consequences.

A celebration for the few, a responsibility for all

Let’s face it, not everyone can — or wants to — spend thousands to watch a horse race in person. The Kentucky Derby is a cultural spectacle that serves the elite. But estate planning? That’s for everyone.

Whether you’re a middle-class family, a single parent or a young professional just getting started, estate planning ensures your wishes are respected, your loved ones are protected, and your assets are distributed responsibly.

You don’t need a million-dollar hat to justify creating a will. You just need:

  • Assets, no matter how modest (a car, a home, a savings account)
  • Dependents, like children or aging parents
  • Wishes, about your medical care, guardianship or charitable giving

The misconception that estate planning is only for the rich is not only outdated — it’s dangerous. Without a plan, your family could face court delays, legal confusion, and unnecessary stress.

Planning with purpose

Consider this. Wealthy Derby-goers don’t just plan for fun — they plan to optimize their experience. The same mindset should apply to estate planning. You’re planning for peace of mind, clarity and control. You’re making sure that, in times of loss or crisis, your family is not left scrambling.

And here’s the truth. You don’t need wealth to need a plan. You need purpose.

Final thoughts: trade the hat for a legacy

Attending the Kentucky Derby might be about image, but estate planning is about impact. One lasts a weekend, the other lasts a lifetime — and beyond.

So if you’ve ever marveled at the dedication, extravagance and style that goes into preparing for the Run for the Roses, take a moment to ask: have I spent even a fraction of that time preparing for my future? For my family’s well-being?

Because while Derby hats fade and parties end, a well-crafted estate plan lives on as your legacy.

Stacy Bush is with Bush Wealth Management. This information should not be construed by any client or prospective client as the rendering of personalized investment advice.  For more information, please visit BushWealth.com for our full disclosures.