A client came into my office last month with a stack of papers and a heavy heart. Her father, a successful Brooklyn business owner, had downloaded a will from an online template service. He signed it, but with only one witness present. That simple error—failing to meet the strict execution requirements of New York law—put his entire legacy at risk. The will was invalid, and the daughter he intended to protect was now facing a prolonged and costly battle in Surrogate’s Court.
Over decades of practice, I’ve seen how small oversights can create generational problems. An estate plan isn’t just a set of documents; it is an act of stewardship. It’s the framework you build to protect your family when you no longer can. Yet, the same preventable mistakes appear time and again, turning deliberate plans into sources of conflict and expense. These are not complex legal loopholes; they are fundamental errors that can undo years of hard work.
The “Good Enough” DIY Will
The temptation to use a low-cost online form is understandable. It feels efficient. But a will is a precise legal instrument, and our state has exacting standards for its creation. Under New York’s Estates, Powers and Trusts Law (EPTL) § 3-2.1, a will must be signed in the presence of at least two attesting witnesses, who must also sign their names and addresses within a 30-day period. The person making the will—the testator—must declare to the witnesses that the document is, in fact, their will.
When these formalities are not scrupulously observed, the will can be challenged and thrown out by the court. I have seen wills invalidated because a witness was also a beneficiary, creating a conflict of interest. I’ve seen them fail because the testator’s signature was in the wrong place. When a will is deemed invalid, the estate is distributed according to state intestacy laws—as if no will ever existed. The outcome rarely matches what the person actually intended.
Forgetting Who You Named as Beneficiary
Many of our most valuable assets pass to loved ones outside of a will. These are non-probate assets and include life insurance policies, 401(k)s, IRAs, and certain bank accounts. They are transferred directly to the person named on a beneficiary designation form.
A beneficiary designation supersedes your will. I cannot count the number of times a divorced client has updated their will to leave everything to their children, only for their ex-spouse to inherit a multi-million dollar retirement account because a form signed 20 years earlier was never changed. Life events—marriage, divorce, the birth of a child, a death in the family—demand a systematic review of these designations. Treating them as an afterthought is a direct path to litigation and unintended consequences.
Planning for Death, but Not for Incapacity
A will only becomes effective upon your death. It does nothing to protect you if you become incapacitated by an accident or illness during your lifetime. Without a durable power of attorney and a health care proxy, your family has no legal authority to manage your finances or make medical decisions on your behalf. Their only option is to petition the court to appoint a guardian.
This process, known as an Article 81 Guardianship proceeding in New York, is public, expensive, and emotionally draining. A judge, not your family, will decide who is best suited to take control of your life. It can take months, during which bills may go unpaid and critical medical choices are delayed. Proper incapacity planning—appointing an agent you trust to act for you—keeps these deeply personal matters within the family and out of the courthouse.
The Empty Trust
A revocable living trust can be a powerful tool for avoiding probate, ensuring privacy, and managing assets for beneficiaries. At my firm, we draft these instruments to serve as a strong container for a client’s legacy. However, a trust is only effective if you fund it—that is, if you legally transfer ownership of your assets into the trust.
Creating the trust document is only the first step. You must then retitle your home, your non-retirement investment accounts, and your bank accounts into the name of the trust. Failure to do so renders the trust an empty vessel. The assets remain in your individual name and will have to go through the public, time-consuming probate process you created the trust to avoid. An unfunded trust is one of the most common and unfortunate errors in estate planning—a wasted opportunity for intentional stewardship.
Correcting these mistakes isn’t about complex legal maneuvers. It’s about diligence and a deliberate approach. The first step is often the simplest. We typically advise clients to begin by requesting a complete list of their current beneficiary designations for every retirement account and insurance policy they own. Seeing it all on one page is the first step toward confirming your plan truly reflects your intentions.
