A few months ago, a family from Brooklyn sat in my office. They had just lost their father, a successful small business owner. In his desk, they found his will—meticulously drafted and signed in 1994. The document was an artifact from another life. It named his second wife, a woman he’d divorced 20 years ago, as his executor. It meticulously divided assets he no longer owned and made no mention of his two youngest children, who were born after it was signed. His intentions were good, but the document he left behind created a legal tangle that would take his family over a year and tens of thousands of dollars to unravel in Surrogate’s Court.
This is not a rare occurrence. In my practice, I see families grappling with the consequences of well-intentioned but flawed estate planning every day. The most damaging mistakes are rarely exotic. They are simple oversights that grow into significant problems under the pressure of grief and legal procedure. True estate planning is an act of stewardship—a deliberate, ongoing commitment to protecting the people you love. It fails when it’s treated as a one-time task to be completed and forgotten.
Mistake 1: The “Set It and Forget It” Plan
The most common error I see is treating an estate plan as a static document. Life is not static. Families grow, children marry, grandchildren are born, assets are acquired and sold, and relationships change. A plan drafted when your children are toddlers is fundamentally unsuited to guide your family when those children have families of their own.
Failing to update a plan has practical consequences. An ex-spouse may remain as a beneficiary or, as in the case of the Brooklyn family, an executor. A person you named as a guardian for your minor children may no longer be able to serve. A trust set up for a specific purpose—like funding a college education—may become irrelevant or insufficient. A prudent review every three to five years, or after any major life event like a marriage, divorce, or significant change in assets, is essential. This isn’t about rewriting everything from scratch. It’s about making intentional adjustments to ensure your plan reflects your current reality.
Mistake 2: Assuming a Will Avoids Probate
There is a persistent myth that if you have a will, your estate will not go through probate. The opposite is true. A will is, in essence, a set of instructions for the New York Surrogate’s Court. The entire purpose of the probate process is to validate that will, appoint the executor you named, and oversee the distribution of your assets according to its terms. It is a public, court-supervised process that can be both time-consuming and expensive.
Probate means your family’s affairs become a matter of public record. It invites challenges from creditors and potential contests from disgruntled heirs. While a well-drafted will can streamline this process, it does not eliminate it. For many of my clients, especially those concerned with privacy or who own property in multiple states, avoiding probate is a primary goal. This is typically achieved through the use of a revocable living trust. When assets are properly titled in the name of a trust, they pass to the beneficiaries outside of the court’s jurisdiction—a private, efficient, and far more direct transfer of your legacy.
Mistake 3: Ignoring Beneficiary Designations
Many of a person’s most significant assets do not pass through their will at all. Retirement accounts—like 401(k)s and IRAs—life insurance policies, and certain bank accounts are transferred directly to the people named on their beneficiary designation forms. These designations operate by contract and will override whatever your will says.
I have seen this create heartbreaking outcomes. A man updates his will to leave everything to his three children, but he forgets to update the beneficiary designation on a life insurance policy he took out 25 years earlier that names only his eldest child. By law, the insurance company must pay the full amount to the eldest child, regardless of the father’s wishes in his will. A coordinated estate plan looks at the entire picture—both probate and non-probate assets—to ensure that every piece of your legacy is directed exactly where you intend it to go.
Mistake 4: Relying on a Generic Online Will
The rise of do-it-yourself legal websites has made it tempting to believe that estate planning can be handled with a simple online form. While these services may be inexpensive, they often create more problems than they solve because they cannot account for the nuances of state-specific laws. New York has a body of law that is highly protective of certain family members, and a generic document can easily run afoul of it.
For example, under New York Estates, Powers and Trusts Law (EPTL) § 5-1.1-A, a surviving spouse has a “right of election.” This law grants the spouse the right to claim a significant share of the deceased’s estate—roughly one-third—regardless of what the will states. A person might use an online form to try and disinherit their spouse, but New York law makes that largely impossible. When the will is submitted to the court, this conflict creates an immediate legal challenge that must be resolved, often through costly litigation. What was intended as a cost-saving measure becomes a false economy, leaving the family with a legal mess that far outweighs the initial savings.
These mistakes are not the result of bad intentions. They are the result of treating legacy planning as a simple transaction instead of a thoughtful, deliberate process. Stewardship requires more than a form—it requires foresight and professional guidance.
If you recognize your own situation in any of these examples, the prudent first step is not to worry, but to get clarity. I invite you to schedule a confidential review of your current estate documents with my team. In that meeting, we will identify any gaps between your documents and your intentions, ensuring the plan you have in place truly protects your family’s future.
