I once met with a family from Long Island whose father had passed away suddenly. He was a meticulous man who believed he had left everything in order. He had downloaded a will from the internet, filled it out carefully at his kitchen table, and signed it. The problem? He had only one neighbor witness his signature. In New York, that document is not a valid will. His entire estate—the result of a lifetime of work—was thrown into the uncertainty of an administration proceeding in Surrogate’s Court, as if he had died with no will at all.
This is not a rare story. Over my career, I have seen well-intentioned plans fall apart because of small, avoidable errors. Estate planning is not about filling out forms; it is an act of stewardship for the people you care about most. A plan that works is deliberate and built to withstand scrutiny. A plan that fails often contains one of several common—and correctable—mistakes.
The Lure of the Do-It-Yourself Will
The father in that story fell into a common trap. He tried to save a little money on legal work, but his family ultimately paid a far higher price in time, stress, and expense. While online templates and software can seem like a straightforward way to create a will, they rarely account for the strict legal formalities required by state law.
New York’s Estates, Powers and Trusts Law (EPTL) is very specific. For a will to be valid, EPTL § 3-2.1 requires that it be signed by the testator in the presence of two attesting witnesses, who must also sign their names. This isn’t just a suggestion—it’s a rigid requirement. If the execution ceremony is flawed, a judge in Surrogate’s Court can and likely will refuse to admit the will to probate. The result is that your assets will be distributed according to the state’s intestacy laws, which may be completely at odds with your wishes.
A properly drafted and executed will is more than a document—it is a set of clear instructions for the court and your family, created to prevent ambiguity and conflict. Taking a shortcut on this foundational step is a risk I never advise my clients to take.
Choosing the Wrong Custodian for Your Legacy
Your estate plan relies on people to carry it out. The person you name as your executor, trustee, or agent under a power of attorney is your fiduciary—a custodian entrusted with immense responsibility. One of the most damaging mistakes a person can make is choosing the wrong individual for this role.
It is tempting to name your eldest child or a close friend as a default. But the right choice has little to do with birth order or affection. A fiduciary must be organized, impartial, financially responsible, and able to communicate clearly, especially under pressure. Their duties are significant: gathering assets, paying debts and taxes, managing investments, and distributing property to beneficiaries, all while acting in the beneficiaries’ best interests.
When a fiduciary is not up to the task, the consequences can be severe. I have seen estates depleted by mismanagement and families torn apart by an executor who plays favorites or lacks the transparency required by law. The role is not an honor; it is a job. Before naming someone, ask yourself honestly: Is this person capable of managing complex financial and family dynamics? If there is any doubt, it is often more prudent to consider a professional or corporate fiduciary.
Overlooking Beneficiary Designations
Many people believe their will controls the distribution of all their assets. It doesn’t. Certain assets pass directly to a named person upon your death by operation of law, entirely outside of the probate process. These are often some of the most valuable assets you own:
- Life insurance policies
- Retirement accounts (401(k)s, IRAs)
- Annuities
- Bank accounts designated as “Payable on Death” (POD) or “In Trust For” (ITF)
The beneficiary designation form you filled out for these accounts—perhaps decades ago—is a binding contract. It will override whatever your will says. I have seen a 401(k) worth over a million dollars go to an ex-spouse because a client forgot to update his beneficiary form after a divorce. His current wife and children, the intended heirs in his will, received nothing from that account.
Intentional estate planning requires a periodic audit of these designations. Marriage, divorce, the birth of a child, or the death of a beneficiary are all life events that should prompt an immediate review. Leaving these forms unexamined is like leaving a door unlocked; you are inviting an outcome you never intended.
This isn’t just about avoiding conflict. It’s about ensuring your stewardship is complete. Your legacy is the sum of all your planning, not just one part of it.
If you have not reviewed your will, trust documents, and beneficiary designations in the last three to five years, the plan you have may not be the plan you think you have. The first step toward correcting these potential errors is a deliberate review of your existing documents. We regularly schedule a 30-minute audit with families to identify these and other potential points of failure before they become a problem.
