Five Estate Planning Pitfalls and How to Avoid Them

The one thing Ann J. can say for certain about her mother’s estate plan is that it’s a work in progress. And her mother is 92. “Just recently, we found out that she has a new plan for the properties we thought were earmarked for me and for my brother,” says Ann, 65, a teacher in Northampton, Massachusetts, who is not using her last name to protect her privacy.

Because Ann’s mother has managed her own finances since a rough divorce many years ago, Ann assumed her mother would have long settled the plans for her estate. But, Ann admits, she never probed too deeply, because her mother rarely wanted to discuss any details. “Now we’re realizing that there are a lot of gaps in her plan,” Ann says, with some frustration. “I think we need to step in. But to be honest, she’s still in control and doesn’t want our input at all.”

The road to a fully executed estate plan is rarely smooth, despite the best intentions of all involved, says Shaila Buckley, an estate planning attorney in Boise, Idaho. “You’re dealing with the intersection of death and money, and people are not always their best selves,” she says.

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Nonetheless, many estate planning experts say that some of the thorniest problems are among the most common. With professional support, many of these issues — from administrative hiccups to disputes over what’s fair (and for whom) — it’s possible to shield your own plan from some of the more preventable snafus.

A pre-warning: Owing to the potential for conflict, addressing these issues during the holidays may not be ideal. Emotions run high this time of year, and there is great potential for conflicts. Use the holidays to reflect on some of these tasks. With a bit of foresight and professional support, many estate planning hurdles can be ameliorated — or avoided altogether.

1. Leaving your plan unfinished

The challenge. At the top of the list is the very issue Ann J. and her brother are contending with: Their 92-year-old mother’s reluctance to finalize her plan. It's a well-known fact that few people have a will or estate plan: only 24%, according to Caring.com’s 2025 Wills and Estate Planning study, a substantial decrease from the 33% in 2022 who said they did have a will. Just as concerning are the numbers of families with incomplete plans: Unsigned paperwork, assets that haven’t been transferred to an existing trust, or a tough decision left hanging can hold up an estate plan for years.

There’s a technical term for this, says Buckley: “We call it waiting too long, and it can be disastrous.”

Many people know that dying “intestate” (without a valid will) means that your assets would be distributed by law, not according to your wishes. What many people don’t realize is that if there are existing documents — say, a trust or will set up many years ago —“those become the controlling documents, and your assets are distributed accordingly,” says Buckley.

Worse, Buckley adds, is if families wait to resolve a delay, and the individual in charge of the plan becomes ill, or an attorney deems them incapable of making legal decisions. In that case, the last valid documents also prevail, whether the person wanted it that way or not.

What to do. The first step, says Jonathan Kolmetz, a certified financial planner and a licensed therapist who practices financial therapy in Houston, is to not address the obvious problem: i.e., a distrust of lawyers or a pattern of putting things off. For many in the Baby Boom generation and older, the taboo about discussing money — with adult children or sometimes even between two members of a couple — can be a powerful undercurrent. “Often, a couple has a certain communication style that has functioned for them in certain ways, but now it’s holding up the process,” Kolmetz says.

The quieter person in a couple may have preferences they’re not expressing. Or, as in the case of Ann J.’s mother, there may be unspoken fears — left over from her divorce or her own family’s history — that she’s trying to manage by keeping her kids in the dark. The key is taking the time, perhaps getting professional support, to foster a more empathetic conversation. “When we can slow down and actually listen to each other, that creates more awareness,” says Kolmetz. “It can lessen conflict, so we can empathize — and that really does help people move forward.”

2. Keeping your estate plan to yourself

The challenge. How much of your estate plan should you share with your family? And for those with older parents: How much should you expect them to share with you? The issue of transparency is a big hurdle for many families, because there are arguments in favor of saying more as well as saying nothing at all.

What to do. One advantage of being more transparent is that it allows heirs to raise questions directly with the older generation. “I see so many fights between siblings about what their mom and dad intended,” says Lucas Spaeth, an attorney in Edina, Minnesota. “I often wish they’d been able to speak up while their parents were still alive.”

Wouldn’t sharing an estate plan with family members open the individual or couple to potential arguments and debates? Buckley agrees that there could be hurt feelings or conflicts. “But if there’s an unequal distribution or a disinheritance, at least people know what’s coming,” she points out.

That may create additional friction, but it also allows for conversations about what’s equitable (more on that below) and/or desirable. Kolmetz recounts a story about a family where a set of antique china wasn’t in dispute (one sibling wanted it, the other didn’t). But the cost of storing the delicate items became a point of contention — and could have easily been sorted out before the parents passed. “I’m in favor of being transparent when it helps resolve important questions,” he says.

That said, warns Spaeth, “You don’t necessarily want your estate plan to become a family affair.” In some cases, it may be better to keep your plan private, especially if you think your loved one won’t be able to resist the desire to give their opinion or push their own agenda (see the TV series Succession for reference).

Failing to let others know what you consider 'fair'

The challenge. It is a truth universally acknowledged, or close to it, that parents rarely distribute their assets evenly among their children while they’re alive. One child may have gotten help with debt, a down payment on a home, graduate school or support for medical or mental health issues that another sibling didn’t. The scenarios are endless, and the shadow of “this one got more” can quickly derail a couple’s estate plan, says Ashley Agnew, a senior wealth adviser and certified financial therapist in Needham, Massachusetts.

What to do. The key, says Agnew, is to figure out what’s fair — for you and your family. “There truly are no right answers for dividing your assets,” she says. “What’s equal isn’t always equitable. For most people, ‘fair’ is a feeling, not a fact.”

That’s not to say that allocating your assets evenly between your children is the wrong way to go. A mathematical split among your heirs can keep things simple on one level, without trying to rectify the imbalances of the past. In most cases, though, these are hard choices that require compassionate conversations, says Kolmetz. “Often, what’s holding up a couple’s plan isn’t the dollar amounts; it’s that they each need to express what fairness means to them. What did ‘being fair’ look like in their own families growing up? How does that translate to their own children and grandchildren now?”

The issue of fairness comes up in force with blended families, Agnew notes, making open conversations even more important. For example, she says, if a couple is in a second marriage, and one spouse has two children from a prior marriage. In contrast, the other has three. Should the assets of each spouse be divided equally only among their biological children?

Shaila Buckley agrees that exploring what’s fair and equitable — even when it’s uncomfortable — can help prevent far worse outcomes later on. “You absolutely have to put in time to have these discussions before someone dies, because this is the single most common type of litigation in estate planning.”

4. Worrying too much about estate taxes

The challenge. Another common cause of handwringing and confusion when setting up an estate plan is the impact of taxes, says Buckley. If you have a large estate, it could face federal taxes on the total fair market value of all assets at the time of your death (including real estate, investments, retirement accounts, cash and more).

In addition, 11 states and the District of Columbia (Connecticut, Hawaii, Illinois, Massachusetts, Maine, Minnesota, New York, Oregon, Rhode Island, Vermont and Washington) also levy estate taxes, and five more have an inheritance tax levied on beneficiaries (Iowa, Kentucky, Nebraska, New Jersey and Pennsylvania). Maryland takes a bite coming and going with both an estate tax and an inheritance tax.

What to do. While the ultra wealthy will need to consider estate and inheritance taxes, most people won’t, says Buckley. “Most people don’t understand that they’re not going to pay any estate taxes unless their estate is worth more than $15 million as an individual, and $30 million as a couple [for 2026]. So most people don’t even have to plan for estate taxes anymore.”

In fact, many people don’t realize that in both community property states and common law states, there is a step-up in basis for investments and real property, which can provide a substantial tax break for heirs, says Buckley. Say you bought 100 shares of Apple stock 20 years ago, at $10,000, and when you died, the fair market value of the stock was $100,000. If you sold the stock the day before you died, you’d owe capital gains on the profit: $90,000. But after you die, your heirs wouldn’t owe capital gains on that $90,000.

5. Relying on AI to write your plan

The challenge. A scourge of these high-tech times, estate planners say, is the temptation to use online or AI-generated estate plans. “They’re horrendous, and most people don’t know what they’re doing when they use these services,” says Buckley.

While these options may seem efficient and inexpensive, you or your heirs could end up spending far more time and money unraveling what these documents do and don’t cover. “The main issue is that these services aren’t state-specific and often misuse legal terms,” adds Spaeth, “which could trigger a formal probate proceeding, which would greatly increase the cost of administration.”

What to do. Buckley acknowledges that it may sound biased for an estate attorney to recommend using … an estate attorney, “but you really want the expertise that a trained estate lawyer can provide.”

Note: This item first appeared in Kiplinger Retirement Report, our popular monthly periodical that covers key concerns of affluent older Americans who are retired or preparing for retirement. Subscribe for retirement advice that’s right on the money.

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