A few years ago, a new client came to our Madison Avenue office with a will he’d created online. He was proud of his foresight. He believed he had protected his family. But as I reviewed the document, I saw not a plan, but a map of future problems. He had named no guardian for his young children, leaving their fate to a judge. He had made no provision for his Lower East Side co-op, which had strict transfer rules. And by relying on a will alone, he had unknowingly guaranteed his family a long, public, and expensive journey through Surrogate’s Court.
This is a story I see in different forms every week. Good intentions are not enough to build a lasting legacy. Stewardship requires deliberate action and an understanding of how easily a lifetime of work can be undone by a few common oversights. These are not clerical errors—they are fundamental failures of strategy that can cost a family dearly.
Relying on a Will Alone
Many people believe a Last Will and Testament is the cornerstone of an estate plan. It is an essential document, but it is an incomplete foundation. A will is a set of instructions for a judge. It has no power until the person who signed it—the testator—has passed away, and the will is admitted to probate by the Surrogate’s Court.
Probate is the court-supervised process of validating the will, appointing an executor, paying debts, and distributing assets. It is a public proceeding. The will becomes a public record. The estate’s inventory—what you owned and what you owed—can become public information. For families who value privacy, this is an unwelcome discovery.
The process is also slow. It can take months, sometimes years, to finalize. During that time, assets may be frozen, and beneficiaries must wait. A properly structured and funded revocable living trust, by contrast, avoids probate for the assets it holds. The transition is private, efficient, and managed by a trustee of your choosing—not a court schedule.
Ignoring Beneficiary Designations
A dangerous assumption is that your will controls the distribution of all your assets. It does not. Certain assets pass directly to a named person by operation of law, entirely outside the will and the probate process. These are non-probate assets.
Think of your life insurance policies, 401(k)s, and IRAs. When you opened those accounts, you filled out a form naming a beneficiary. That designation is a contract, and it supersedes any instruction in your will. I have seen this create tragic, unintended outcomes. A client updates his will after a divorce to leave everything to his children, but he forgets to change the beneficiary on a seven-figure life insurance policy. His ex-spouse, named years earlier, receives the entire payout. The will is irrelevant.
An intentional estate plan involves a regular audit of all beneficiary designations to ensure they align with your current wishes. Overlooking this simple step can redirect generational wealth.
Choosing the Wrong Fiduciary
Your estate plan is only as effective as the people you empower to carry it out. The roles of executor, trustee, and agent under a power of attorney are not honorary titles. They are jobs with immense responsibility and significant legal liability. This person or institution is your fiduciary—they have a legal duty to act in the best interests of the beneficiaries.
Choosing your oldest child out of tradition or a close friend because you don’t want to offend them is not a strategy. Is this person financially savvy? Are they organized? Can they remain impartial when siblings are demanding their inheritance? Can they handle the administrative burden of managing investments, filing taxes, and communicating with beneficiaries?
A fiduciary can be held personally liable for mismanaging assets. The role requires a specific skill set and temperament. Sometimes, the most loving choice is to name a professional or corporate trustee who is equipped to handle the duties dispassionately and effectively.
Forgetting to Fund Your Trust
A revocable living trust is a powerful tool, but only if it is used correctly. I often see clients who have spent the money to create a trust, signed the documents, and then failed to take the final, crucial step: funding it. A trust is like a vessel. It can only control the assets that are actually placed inside it.
Funding a trust means retitling assets from your individual name into the name of the trust. This includes real estate deeds, bank and brokerage accounts, and business interests. If you create a trust but the deed to your Brooklyn brownstone remains in your name alone, the house is not governed by the trust. It will have to pass through probate, defeating one of the primary reasons for creating the trust in the first place.
An unfunded trust is merely a stack of paper.
Misunderstanding a Spouse’s Rights
New York law provides specific protections for a surviving spouse, and a plan drafted in ignorance of them will fail. You cannot completely disinherit your spouse through a will. Under the Estates, Powers and Trusts Law (EPTL) § 5-1.1-A, a surviving spouse is entitled to a “right of election.”
This statute gives the spouse the right to claim a share of the deceased’s estate, regardless of what the will says. The elective share is the greater of $50,000 or one-third of the net estate. This right is powerful and can override a plan that attempts to leave all assets to children from a prior marriage. While a spouse can waive this right in a valid prenuptial or postnuptial agreement, you cannot simply write them out of the will. An estate plan must be built on the reality of the law, not on wishful thinking.
A well-crafted plan is an act of stewardship. It anticipates contingencies and provides clear direction, ensuring your legacy is a source of support for your family, not a source of conflict. The first step is to understand what your current documents do—and do not—accomplish.
To see where your own plan may have vulnerabilities, schedule a confidential review of your existing will or trust. My firm uses this process to identify potential gaps before they become irreversible problems for your family.
