What is Estate Planning? An Interview with John O’Grady

It’s never easy to talk about death. When it comes to talk of wills, trusts and end-of-life care decisions, the conversation becomes even more difficult for families and loved ones. Mediator and Estate Planning Lawyer John O’Grady guides people through these difficult conversations and helps resolve their battles so they can stay connected through tough times.

John’s path to pursue this work is personal. Soon after graduating from law school, John’s sister, her husband and their infant son were tested HIV positive. John’s journey through grieving the illness and the loss of his loved ones was the most painful and transformative experience of his life. Because of this first-hand experience, John is adept at encouraging people to talk about “unspeakable” issues like death.

I talked with John about broaching this difficult conversation, getting estate planning started, and easing the difficulties of life after a loss by understanding and attending to the legal issues early.

Dana: I’ve been told that possessions are one of the least taboo topics to bring up regarding the death conversation. Do you find that people have an easier time talking about estate planning, versus, for example, what kind of death they want to have, or their funeral, etc?

John: Yes. Death is an emotional issue. The skill in my work is the art of looking at their denial. There are many ways to do that. Talking about possessions is one of them. Another angle on it is when people are talking to their parents about doing a will and a trust, the parents don’t like that idea and think the kids are being greedy. But the kids just want it to be clear and simple. Often without a trust it has to go through the court system, but good planning can make life easier for the kids [after their parents’ passing].

Dana: Do you think that’s because they don’t want to talk about death?

That’s part of it, and also often this is the first time in their lives that they’re talking about money. Also, older people are very sensitive about discrimination and agism, and they don’t want to be written off as “dead.” And often signing a will is equated with being dead.

Denial is the name of the game. To sign a will and trust, you need to face the trauma of your own dying. It’s on everyone’s “to-do list,” but at the very bottom until there’s a crisis. People will call me before flying to Europe, for example. There’s an irrational fear that flying is dangerous.

Dana: So they want to have their “affairs in order?”

John: Yes. And there are a couple of other crises that make them think about it. One is a terminal diagnosis. Even with that, though, we’ll have people that wait until the last minute. They even procrastinate then! They have a hard time facing the fact that they’re going to die.

The other one is someone close to them dying, and it gets them thinking about their own death. But nobody is planning to die this year, so the vast majority of people just put it off indefinitely, which means that most of my work is cleaning up disasters that could have been avoided with a little planning.

Dana: What do you recommend to people to get that conversation started and make it easier?

John: Everybody’s busy, and they have a long story for why they can’t get started. So I say, “What could be more important than taking care of yourself and your loved ones with estate planning?”

Dana: So, impressing the importance of it on them, or explaining the disasters that you face if it isn’t taken care of?

John: Well, not really. It’s not me telling them what to do, because then they’ll be defensive. I get them talking about it themselves and why they think their other affairs are more important than estate planning. It’s not a rational thing. If it was a rational thing, everybody would have an updated estate plan.

The reality is that less than ten percent of American adults have an up-to-date estate plan.

Dana: Can you talk about the emotional issues that arise with estate planning?

John: There’s lots of sibling rivalry, and rivalry with a new spouse, things like that. I provide a structured counsel to my clients. There are several repetitive family dramas that re-occur. A lot are replays of old Greek classic tragedy.

There’s the Cinderella theme — stepchild in conflict with the stepmother. There’s Shakespeare’s King Lear, where the king tries to get the kids to fight with each other to determine who’s worthy of being the king. There’s the caregiver kid and the untrustworthy trustee.

Dana: The Caregiver Kid?

John: Typically, this is a woman, because women tend to be more concerned about caregiving. Sometimes the caregiver kid gets access to all the money and is receiving gifts the other kids aren’t giving.

Dana: Kind of a favoritism thing?

John: Yes.

Dana: What are a person’s estate planning options? What kinds of things should people be thinking about to get started?

John: Mainly, do something. Because these are really big decisions. Part of the paralysis is that these are such big decisions, and people want to put them off. I tell them, these won’t be perfect decisions, and you can change your mind as long as you’re alive, so you might as well make some kind of decision now. After you sign the documents you’ll get more information about whether that’s what you really want. But you have to start somewhere, so do something.

The first step is to always call a lawyer. Make an appointment with the lawyer and get it on the calendar. Otherwise, it’s just an abstract idea. When it’s an appointment on your calendar, you have to show up for it. It’s off your to-do list and on your calendar.

I always remind clients that it doesn’t cost anything to make the appointment, so cost doesn’t have to be a barrier to taking that first step.

Dana: How early do you recommend starting this planning?

John: Actually, young people should have an advanced healthcare directive — they’re the ones taking all kinds of risks, riding motorcycles, jumping off of cliffs. The reality is that most people who have them are over sixty and not taking risks anymore. I recommend young adults have a will and an advanced healthcare directive. In California, they should have a trust if non-retirement assets are worth $150,000 or more, and every jurisdiction has slightly different laws. Some also have different names for the documents (some call an advanced healthcare directive a “living will.”)

Dana: Is the planning usually more or less complicated than people are anticipating?

John: It’s hard to say. You never know what’s going to happen in the process, how the family conversation will go, what the lawyer will ask, how the spouses will react. People want to know the cost [of the whole process] in the first phone call, and I can never really tell them. How much it costs is up to them. In the initial phone call, I explain the process to them in great detail, and what the major questions are [throughout the process].

Dana: Can you name some of those questions?

John: Who will be the executor or trustee (in charge of the money)? Who’s going to decide that the day has come that I’m incapacitated? Who’s going to get what?

There’s a whole lot to discuss, even just the question of who’s going to be the trustee. I teach an entire class on choosing the trustee.

Thanks for taking the time to talk with us, John!

You can learn tons more about estate planning from John through his website, and get more info about his lectures and classes by signing up for his newsletter.

For more on this topic, keep an eye out next week for John’s Ten Tips for Estate Planning! You can also learn more about estate planning in SevenPonds’ Before Death information library.

Image credit: Stock xchng; head shot courtesy of John O’Grady