Ideas in the Wild: James L. Cunningham, Jr. Shares Common Estate-Planning Mistakes to Help Protect Our Legacies

Zach Obront
Authority Magazine
Published in
5 min readMar 8, 2022

Too many people make the wrong choices when it comes to estate planning. If it’s not done properly, it can have dire consequences.

In this no-nonsense guide, attorney James L. Cunningham, Jr. shows how to avoid the top 10 mistakes that could damage your financial succession, family, heirs, and legacy. He gives an unvarnished picture on probate, living trusts, living wills, powers of attorney, conservators, and guardians, as well as disability and incapacity planning, how to find the right attorney, and what issues to discuss with them.

Ultimately, the second edition of Savvy Estate Planning provides the essentials everyone needs to know about estate planning. I recently caught up with Jim to learn more about why he wrote the book and the ideas he shares with readers.

Why did you write the book?

In my 20 years as an estate planning attorney, I’ve noticed something: even though our values and relationships are certainly more important than our money, the way we use and pass on money reflects our values, and can help embody our relationships, our loves, our accomplishments, our intentions, and our legacy.

As adults, many of us have learned the following hard lesson: doing money right usually means doing a lot of other things right. In fact, when I hear people say, “It’s not about the money,” alarm bells go off in my head. Somewhere along the line, I know it definitely will be about the money — and that includes estate plans.

Estate planning is a complex subject, and I didn’t write this book to teach people how to do it all themselves. That would be impossible. Situations are too varied. The laws and priorities keep changing. The stakes are too high, and the pitfalls too large for you to avoid using an attorney to help with your estate plan. Period.

But this book will help you understand the big picture of estate planning and empower you to move forward with confidence. I want to get you past the denial and paralysis that plague most people approaching this subject. I want to help you pick the right attorney, and make sure he or she is covering all the bases. I want to ensure that you stay on top of your situation and leave the legacy you want and deserve.

Most of all, I wrote this book to help people stop making the big mistakes. I want to see happier families. Joyful legacies. Less time in courtrooms. Less taxes paid. Peace among children, parents, siblings, and spouses.

What’s an idea you share that really excites you?

When your kids were little, you wouldn’t let them run in the street. When they were teens, you wouldn’t let them stay out until dawn. When they became adults, you wouldn’t let them send money to Nigerian princes soliciting them by email. And when you die, believe me, you should not let them go to probate court, not if there’s anything you can do to prevent it.

And guess what? You can.

How? Create a good estate plan with its foundation in a living trust.

You can think of a living trust as a kind of vessel, a bucket which you create, and into which you place your stuff. Basically, when your stuff goes into a bucket, it’s a lot easier for you to carry around, a lot easier to track, and a whole lot easier to pass on to another person.

Forgive me for extending the metaphor, but if your stuff is not in a bucket, when you die, it falls onto the ground. Then other people have to find it, figure out who owned it, and go to court to prove it’s now theirs. Only then can they pick it up off the ground.

When you (or you and your spouse) create a living trust, you literally transfer many of the things you own into that trust. And while you are alive, you remain in control of that trust. When you die or become incapacitated, you give control of your trust to someone else.

Because, according to law, the living trust owns all that stuff, and the trust survives you, no probate is required. There is nothing to prove to a judge. No “probare” needed. The trust continues to be the legal owner of the assets. Control of the trust simply passes to a new trustee.

A living trust may sound like a legal fiction, but it is not. Living trusts are the very sensible way our society has devised to make succession easy, logical, and low cost. Trusts are the way we preserve legacies — a way of cheating some of the chaos created by death.

How will following your advice improve your readers’ lives?

Estate planning is complicated. It’s too complicated to do by yourself. But, if I did my job with this book, once you are done reading it, you will have a pretty solid idea of what you don’t know about estate planning.

If you feel more confident about walking into a firm of estate attorneys and making sure they do their job, that’s a bonus. If you have peace of mind — if you go to sleep each night knowing that none of the big questions regarding your estate have been left undiscussed — I’ll take that as a win.

If you feel empowered to make decisions, make them now, and keep on making them, then I will have truly fulfilled my mission.

Ultimately, after you read this book, you will have taken a big step towards taking control of your life in the here and now. And of course, right along with that, you will be that much closer to leaving a beautiful legacy.

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