I once met with the children of a successful Brooklyn business owner, just weeks after his funeral. They were reeling. Their father had remarried late in life and, to keep things “simple,” had downloaded a will from the internet. He signed it at his kitchen table and told his children everything was taken care of. But his will left his entire estate—the business, the family home, everything—to his new wife, completely disinheriting the children who had helped him build his company. They came to me hoping to contest the will, but the document was technically valid. What their father didn’t understand was a fundamental principle of New York law.
Planning for your legacy is not about filling out forms. It’s an act of stewardship. It’s the final and most lasting way you provide for the people you love. Yet in my practice, I see the same avoidable missteps time and again. These aren’t obscure legal technicalities—they are fundamental errors that can create lasting conflict and undermine a lifetime of hard work.
Relying on a Document Instead of a Plan
The most common mistake I see is believing that a simple, do-it-yourself will is a substitute for a real estate plan. These template documents can create a dangerous illusion of security. They fail to account for the specifics of New York law and the unique dynamics of your family. For instance, that Brooklyn father believed he could disinherit his spouse if he stated it clearly in his will. He was wrong.
Under New York’s Estates, Powers and Trusts Law (EPTL) § 5-1.1-A, a surviving spouse has a “right of election.” This statute grants them the right to claim a significant portion of their deceased spouse’s estate—roughly one-third—regardless of what the will says. The father’s attempt to leave his children everything through a new will would have been just as ineffective. His “simple” document didn’t just fail to achieve his goals; it set the stage for a painful and expensive court proceeding between his children and his widow.
A proper plan anticipates these rules. It uses trusts, beneficiary designations, and other tools to achieve your specific goals in a way that the law will uphold. A document is static—a plan is a deliberate strategy.
Choosing a Caretaker, Not a Fiduciary
When you name an executor for your will or a trustee for a trust, you are not giving out an honorary title. You are appointing a fiduciary—someone who is legally required to act in the best interests of the estate and its beneficiaries. It’s a demanding job that requires financial acumen, impartiality, and a significant time commitment.
Too often, people default to naming their eldest child or a close friend without considering if they are suited for the role. I’ve seen executors who live across the country, struggling to manage the sale of a Manhattan apartment. I’ve seen trustees who lack the financial discipline to manage a large inheritance for a young beneficiary. Naming the wrong person can lead to mismanagement, family resentment, and even litigation.
The choice should be intentional. Is this person organized? Are they responsible with their own finances? Can they communicate effectively and navigate potential conflicts between beneficiaries? Sometimes, the most loving choice is not a family member, but a corporate trustee or a professional who can administer the estate with impartiality and expertise.
Forgetting That Life Changes
An estate plan is a snapshot in time. It reflects your life, your assets, and your relationships on the day you sign it. The third critical misstep is failing to update that plan as your life evolves. A birth, a death, a divorce, a significant change in wealth—all of these events can have profound implications for your estate plan.
The most dangerous oversights often involve beneficiary designations. Assets like 401(k)s, IRAs, and life insurance policies are non-probate assets. This means they pass directly to the person you named as the beneficiary, completely outside of your will. I have seen cases where a person’s will leaves everything to their current spouse, but their multi-million dollar life insurance policy still names an ex-spouse from a decades-old divorce. No matter what the will says, that money goes to the ex-spouse. The will is powerless to change it.
A prudent plan includes a regular review—every three to five years, or after any major life event—to ensure your documents and beneficiary designations align with your current wishes. Without this, you risk unintentionally disinheriting the people you most want to protect.
Failing to Plan for Incapacity
Many people focus entirely on what happens after they die, but they neglect to plan for a period of incapacity—a time when they might be alive but unable to make financial or medical decisions for themselves. Without a plan, your family’s only option may be to petition a court to appoint a guardian. This is a public, expensive, and often emotionally draining process that strips you of your autonomy.
A prudent plan always addresses this contingency. A durable Power of Attorney allows you to name an agent to handle your financial affairs. A Health Care Proxy allows you to appoint someone to make medical decisions on your behalf. These are not merely administrative documents. They are profound statements about who you trust to be your custodian and advocate when you cannot speak for yourself.
These missteps are not failures of wealth, but failures of intention. True stewardship is about more than signing a document; it’s about building a resilient plan that protects your family, preserves your legacy, and functions as you intended. It is one of the most significant things you will ever do for them.
The first step toward a more deliberate plan is often a straightforward review of your existing documents. I invite you to schedule a consultation with our firm to perform an audit of your current will, trusts, and beneficiary designations to identify any of these common gaps.
