A few years ago, three siblings walked into my office. Their father, a successful small business owner in Queens, had recently passed away. They brought with them a will he’d downloaded from a website for $49.95. He thought he had taken care of everything. But the document was a disaster—it hadn’t been witnessed properly, and one of the signature pages was ambiguous. Instead of a straightforward administration, that family spent the next 18 months and tens of thousands of dollars in Surrogate’s Court proving the will was valid. Their father’s attempt to save a little money ended up costing his children a significant piece of their inheritance.
I see the consequences of well-intentioned but misguided decisions every day. An estate plan isn’t just a set of documents; it is the final act of stewardship for your family. It’s the framework that protects them when you no longer can. Yet simple, avoidable errors can undermine that entire structure. Here are four of the most common missteps I see.
1. Relying on an Internet Will
That family’s story is not unique. Online legal documents promise a quick and cheap alternative to working with an attorney, but they are a minefield of risk. These templates are generic by nature. They cannot account for the specifics of your family—a child with special needs, a complex business succession, or a second marriage. They also frequently fail to comply with New York’s strict legal formalities.
Surrogate’s Courts demand that a will be executed with precision. If the signing ceremony is flawed, if the witnesses aren’t credible, or if the language is unclear, the entire document can be challenged and thrown out. The result is a costly, public, and emotionally draining court battle that pits family members against each other. What seemed like a bargain becomes one of the most expensive mistakes a person can make.
2. Forgetting About Beneficiary Designations
Many people believe their will controls the distribution of all their assets. It doesn’t. Significant assets like life insurance policies, 401(k)s, IRAs, and certain bank accounts pass directly to the individuals named on their beneficiary designation forms. These designations supersede whatever is written in your will.
I’ve seen cases where a man’s will leaves everything to his current wife, but his multi-million dollar life insurance policy still names his ex-wife from a divorce 20 years prior. That was his intent two decades ago, but he never updated the form. By law, the insurance company must pay the ex-wife. His widow and children receive nothing from that policy. This isn’t just a clerical error; it’s a failure of stewardship that can redirect generational wealth and create profound hardship for the people you intended to protect.
3. Choosing the Wrong Fiduciary
Selecting an executor for your will or a trustee for your trust is one of the most critical decisions in your plan. Many people default to naming their oldest child, viewing it as an honor. It is not an honor—it is a demanding job with immense legal and financial responsibility. This person, your fiduciary, is tasked with marshalling your assets, paying your debts and taxes, and distributing your legacy according to your wishes.
Is your proposed executor financially responsible? Are they organized? Do they get along with their siblings? A person who is well-meaning but lacks the financial acumen or emotional fortitude for the role can cause irreparable damage. Choosing a fiduciary should be a deliberate, objective decision based on who is most capable of executing the duties required, not who might feel slighted otherwise. Sometimes the most prudent choice is a neutral third party or a corporate trustee.
4. Believing You Have No Plan
The most dangerous misstep is inaction. Many people put off planning because they think it’s too complex or because they believe they don’t have enough assets to matter. But if you fail to create your own plan, the state of New York has one for you. It’s called the law of intestacy.
Under New York Estates, Powers and Trusts Law (EPTL) § 4-1.1, the government dictates who inherits your property. If you die with a spouse and children, your spouse does not inherit everything. Instead, they receive the first $50,000 and half of the remainder, with your children inheriting the other half. This statutory formula rarely aligns with what a person would have wanted. It can force the sale of a family home or create financial strain for a surviving spouse. By doing nothing, you are still making a choice—you are choosing to let the government, not you, decide the fate of your legacy.
A proper plan is an intentional act. It ensures your wishes are known, your family is protected from court intervention, and your assets are passed to the people and causes you care about. It is the final, most important expression of your life’s work.
Before an emergency forces the issue, a prudent first step is to review where things stand today. We often begin our work with new clients by conducting an audit of their existing asset titles and beneficiary designations. This review can immediately identify critical gaps between your documents and your intentions.
