I recently met with the adult children of a successful Brooklyn business owner who had passed away. They brought me his will, a perfectly valid document drafted 25 years ago. The problem? The man he had named as his executor—his best friend and business partner—had died three years prior. He never named a successor. As a result, his family, already grieving, was now facing a lengthy and expensive petition in Kings County Surrogate’s Court to have an administrator appointed.
This is not an uncommon story. Many people view an estate plan as a set of static documents—a will, a trust, a power of attorney. But a plan is not a product you buy off a shelf. It is a strategy. It’s a series of deliberate choices designed to function under pressure, to account for change, and to protect a family’s future. Stewardship.
The Fiduciary Is the Fulcrum of Your Plan
The single most critical decision in any estate plan is the selection of your fiduciaries. These are the people or institutions you name to act on your behalf—your executor, your trustee, your agent under a power of attorney. This is not a ceremonial role or an honor to be bestowed upon a favorite sibling. It is a demanding job with significant legal responsibility.
A fiduciary has a legal duty—a fiduciary duty—to act solely in the best interests of the estate and its beneficiaries. This requires impartiality, financial sophistication, and the fortitude to make difficult decisions, sometimes against the wishes of a family member. When I counsel families, I ask them to think about this choice not as a matter of love, but as a business decision. Who has the skill set, the temperament, and the time to manage your assets, pay your debts, file tax returns, and distribute your legacy according to your wishes?
Every fiduciary choice must include a contingency plan. Naming a single person without at least one or two successors creates a single point of failure. People move, they age, they become ill, their lives change. A well-designed plan anticipates this by naming a sequence of stewards who can step in if the primary choice is unable or unwilling to serve.
Plan for Incapacity, Not Just Death
A common misconception is that estate planning is solely about what happens after you die. In reality, some of the most critical work we do involves planning for a period of incapacity—a time when you may be alive but unable to manage your own financial or medical affairs. Without a plan, your family’s only recourse is to petition the court for guardianship, a public, expensive, and often emotionally draining process.
Two documents are central to this planning: a durable Power of Attorney and a Health Care Proxy. The Power of Attorney authorizes an agent you choose to handle financial matters—from paying bills to managing investments. The Health Care Proxy empowers an agent to make medical decisions on your behalf if you cannot. These are not simple forms. They are powerful grants of authority that must be drafted with precision, appointing people who understand you and can be trusted to honor your wishes without conflict.
The goal is to keep your family out of court. A properly executed plan ensures that if you become incapacitated, the transition of authority is seamless and private, handled by the people you deliberately selected, not a judge who has never met you.
Your Plan Is a Process, Not a Project
The world does not stand still after you sign your estate planning documents. Families grow, assets change, relationships evolve, and laws are updated. Viewing your plan as a one-time event completed years ago is one of the most dangerous assumptions you can make.
A strategic plan requires periodic review—I typically recommend every three to five years, or after any major life event like a marriage, divorce, birth of a child, or significant change in wealth. An outdated plan can produce results that are the exact opposite of your intentions.
For example, New York law has some built-in protections. EPTL § 5-1.4 automatically revokes any disposition in a will to a former spouse upon divorce. While this statute provides a useful backstop, relying on it is poor stewardship. What if you wanted your ex-spouse’s children from another marriage to receive something? What if you owned property jointly? The law provides a blunt instrument—a deliberate update to your plan provides clarity and nuance. An estate plan must be a living strategy, one that adapts as your life does.
This process of review is about more than just changing names. It’s an opportunity to confirm that your chosen fiduciaries are still the right fit, that your asset structure still aligns with your goals, and that your plan reflects your current wishes for the legacy you will one day leave behind.
An effective estate plan isn’t about documents; it’s about outcomes. It’s about ensuring the people you trust are empowered to act, that your family is spared from unnecessary conflict and court proceedings, and that your life’s work is passed on with intention and care. That is the essence of a true strategy.
A valuable first step is to simply read the documents you have. Identify your named executor, trustee, and agents for health and finance. If it has been more than three years since you last considered if these are the right people for the job, schedule a review of your fiduciary designations to ensure they align with your family’s present reality.
