A few years ago, a woman came into my Manhattan office with a will her late husband had downloaded from the internet. He was a successful business owner, and this was his second marriage. He intended to provide for her, his wife of nearly two decades, but the generic form he used was vague. Worse, he signed it alone in his study. In the eyes of the New York Surrogate’s Court, without the two witnesses required by law, the document was worthless. His entire estate was at risk of passing to the children of his first marriage, as if he had died without any will at all.
Over my career, I have seen families consumed by disputes that could have been avoided. The work we do is not about filling out forms—it’s about foresight, stewardship, and building a deliberate plan that withstands scrutiny. Most catastrophic errors do not come from complex tax schemes. They arise from simple, deeply human oversights. Here are some of the most consequential mistakes I see in my practice.
Relying on a Will That Won’t Stand Up in Court
The internet offers a tempting promise: a legally binding will for a few dollars, completed in minutes. The reality is that these documents often create more problems than they solve. New York has strict requirements for executing a will. It must be signed by the testator in the presence of two witnesses, who must also sign their names and addresses within a 30-day period. This is not bureaucratic procedure; it’s a safeguard against fraud and undue influence.
When a do-it-yourself will fails—due to improper signing, ambiguous language, or a failure to account for all assets—the result is often a costly and painful court battle. The few hundred dollars saved upfront can be eclipsed by tens of thousands in legal fees as family members argue over what the deceased truly intended. A will is the instruction manual for the court. If the instructions are unclear or invalid, the judge, not your family, ends up in control.
Forgetting That Beneficiary Designations Override Your Will
Many people assume their will governs the distribution of all their assets. This is a fundamental and dangerous misunderstanding. Certain assets pass directly to a named person by contract, entirely outside the probate process. These are often the most valuable parts of an estate: life insurance policies, 401(k)s, IRAs, and other retirement accounts.
I once worked with a family whose patriarch had meticulously updated his will after a divorce, leaving his entire estate to his two children. He forgot the multi-million-dollar life insurance policy he had taken out 30 years prior, which still named his ex-wife as the sole beneficiary. The will was powerless to change that. The insurance company was contractually bound to pay the proceeds to the person listed on their form. His children, the intended heirs, received nothing from that policy. Stewardship means auditing these designations every few years, especially after a marriage, divorce, birth, or death.
Misunderstanding a Spouse’s Rights in New York
Clients are often surprised to learn that you cannot completely disinherit your spouse in New York. The law provides a powerful protection for surviving spouses, regardless of what a will might say. This is known as the spousal “right of election.”
Under Estates, Powers and Trusts Law (EPTL) § 5-1.1-A, a surviving spouse is entitled to claim an “elective share” of the deceased spouse’s estate. This share is the greater of $50,000 or one-third of the net estate. This right is absolute, unless it was formally waived in a valid prenuptial or postnuptial agreement. Even if a will leaves a spouse just one dollar, they can file a notice of election with the Surrogate’s Court to claim their statutory share. This law prevents the impoverishment of a surviving spouse and underscores the state’s interest in the financial stability of families.
Believing a Will Helps You Avoid Probate
This is perhaps the most common misconception in estate planning. A will does not avoid probate; it guarantees it. A will is a set of instructions for the probate court. Probate is the formal, court-supervised process of validating the will, appointing an executor, paying debts, and legally transferring assets to the beneficiaries.
The process can be time-consuming and is, by its nature, public. For families who value privacy and efficiency, avoiding probate is a primary goal. This is achieved through a revocable living trust. When assets are properly titled in the name of a trust, they are controlled by the trustee you select and can be distributed to your heirs without court intervention. It is a tool for maintaining control and protecting your family’s privacy—a will cannot accomplish this on its own.
A well-crafted plan is an act of profound care for the people you leave behind. It replaces uncertainty with clarity and prevents your legacy from being consumed by conflict.
The first step toward securing your plan is often a straightforward review of what you already have in place. Before considering a new document, I recommend an audit of your existing wills, trusts, and, most importantly, your beneficiary designation forms. We can schedule a meeting to review these documents and identify gaps before they become a problem for your family.
