A Million-Dollar-Plus Estate Planning Mistake You Can't Afford to Make

Imagine this: you and your spouse spend years building a thriving business, growing your wealth, and creating security for your family. You believe your estate plan has every detail covered. But then tragedy strikes—and one overlooked paperwork error leaves your children facing a $1.5 million tax bill they never should have owed.

This isn’t a cautionary tale—it’s exactly what happened to the Rowland family in Ohio. In this article, you’ll learn what went wrong, why mistakes like this are becoming more common among affluent families, and most importantly, how to protect your own legacy from the same fate.

When "Good Enough" Estate Planning Is Not Nearly Good Enough

Billy Rowland was the kind of man who proudly wore a “World’s Greatest Grandpa” cap. Over the years, he grew a string of small businesses across Ohio—trucking, used cars, real estate, even banking. He gave back through charity boards and, on the surface, appeared to have his financial affairs well organized.

When his wife Fay passed away in 2016, her estate filed the required tax return to preserve her unused estate tax exclusion for Billy’s future benefit. It was supposed to be routine paperwork: an estimated estate value and a list of assets—real estate, business shares, the usual.

But there was a fatal flaw. The return never detailed the specific value of each individual asset. To most, it would look like a minor omission. After all, the total value was reported.

It wasn’t minor. That single oversight cost Billy’s heirs $1.5 million when he died in 2018.

Because Fay’s return was incomplete, the IRS ruled that Billy’s estate could not claim her $3.7 million unused exclusion. Without it, his $26 million estate triggered a tax bill that proper planning could have easily avoided.

What makes the story even more painful is the timing. The IRS didn’t question Fay’s return until 2021—five years after her death and three years after Billy’s. By then, the chance to correct the mistake was long gone.

A Problem That is Becoming More Common

hink the Rowland family’s ordeal was a one-off? It wasn’t. In fact, changes in tax law are making mistakes like theirs both more common—and far more costly.

Here’s why: In 2025, each person can pass $13.99 million to heirs tax-free. In 2026, that figure rises to $15 million. For couples who plan correctly, that means as much as $30 million can be shielded from estate taxes.

But there’s a catch. To lock in that doubled protection, the first spouse to die must file a proper estate tax return—even if the estate is small enough that filing wouldn’t normally be required. Miss a detail, and the surviving spouse permanently loses the deceased partner’s unused exclusion.

The consequences can be devastating. With estate taxes at 40% on amounts above the exemption, losing a $15 million exclusion could saddle a family with a multimillion-dollar tax bill. And because estates are often tied up in businesses, homes, or real estate—not cash—heirs may be forced to sell meaningful assets just to pay the IRS. Decades of careful wealth building can unravel overnight.

And this risk isn’t limited to ultra-wealthy families. Nearly 500,000 Americans now hold a net worth of $15 million or more, and many don’t realize they’re sitting on an estate planning time bomb. Even families with smaller estates are vulnerable: investments grow, businesses succeed, inheritances arrive, and exemption amounts shift with each administration. What feels manageable today could easily cross into dangerous territory tomorrow.

Don’t Get Stuck With Planning That Will Fail When You Need It Most

The Rowland family’s story highlights a major problem with the way most people approach estate planning: it’s treated like a one-time task. Draft some documents, sign them, tuck them away, and assume everything will fall into place.

But real estate planning isn’t about paperwork—it’s about building a system that adapts to your life, with guidance from a professional who makes sure your plan actually works when your family needs it most.

Here’s what usually happens: a family meets with a lawyer, creates a will or trust, fills out a few beneficiary forms, and then checks “estate planning” off the to-do list. Years go by. Laws change. Assets grow. Family dynamics shift. But the plan just sits there, frozen in time.

When the first spouse passes away, the surviving spouse—or an overwhelmed adult child—suddenly faces complex tax rules, deadlines, and filing requirements they’ve never heard of. They’re grieving, unprepared, and making high-stakes decisions about legal and financial issues they don’t understand. It’s no wonder critical details slip through the cracks.

This is the fatal flaw of the traditional approach: it focuses on documents, not on people or evolving circumstances. What families truly need is “planning that works.” That means a Life & Legacy Plan—one designed to evolve with you, supported by ongoing guidance to ensure nothing gets missed.

A Life & Legacy Plan includes regular reviews to keep your documents aligned with your life, open conversations with loved ones about your wishes, and the expertise to handle complicated issues like estate tax returns and portability elections.

If Fay Rowland had this kind of support, someone would have verified her estate tax return, confirmed every required detail, and monitored for potential issues before they became costly mistakes. Instead, her family was left to navigate alone—and it cost them $1.5 million.

Creating Protection That Actually Works

The good news is that the Rowland family's nightmare is completely preventable. But it requires a different approach to estate planning—one that prioritizes ongoing relationships and comprehensive planning over simple document creation. That’s what my Life & Legacy PlanningⓇ process is all about. 

Here’s what you need to know about why Life & Legacy Planning works:

Estate planning isn't a "set it and forget it" proposition. Your plan needs to grow and change as your life evolves. This means regular reviews with me, so I can spot potential problems before they become disasters.

If you're married and have significant assets, don't assume that basic estate planning documents are enough. You need a comprehensive strategy that considers tax implications, coordinates with all your other financial planning, and includes proper guidance for complex decisions like portability elections. I have these systems in place.

Make sure your family knows the plan. Too many estate planning disasters happen because surviving family members don't understand what needs to be done or when critical deadlines are approaching. Your loved ones shouldn't be learning about your estate plan for the first time after you're gone. Instead, I’ll support you to have open communication with your loved ones before you die, and be there for them after you die. They’ll never be left wondering what your intentions were, what to do, or how to do it.

Finally, when you work with me, I’m not  just a document preparer. I am a trusted advisor who will be there for your family when decisions need to be made, will ensure that required returns are filed properly, and will monitor changing laws that might affect your plan. You don’t need to worry about your plan failing and your loved ones paying the price, because I’ll be there to ensure it works.

The Rowland family's story is a stark reminder that in estate planning, small details can have enormous consequences. Don't let a paperwork error destroy the legacy you've spent a lifetime building.

Safeguard Your Family's Future

Your family's financial security is too important to leave to chance. The Rowland case shows us that even successful families with significant assets can lose millions because of estate planning mistakes that could have been easily prevented with proper guidance and a trusted advisor who’s there for you throughout your life and for your loved ones after you die.

As a Personal Family Lawyer® Firm, I help families create comprehensive Life & Legacy Plans that actually work when you need them to. My process ensures that your assets are protected, your loved ones understand the plan, and all the technical requirements are handled properly—so you never have to worry about a costly mistake derailing your family's future.

With the right  planning, you can rest easy knowing that your legacy will be preserved exactly as you intended and your life's work will benefit the people you love most.

Don't let your family become the next cautionary tale. Click here to schedule a complimentary 15-minute discovery call and take the first step toward protecting your family's future.