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Willing Wisdom - 7 Questions to Ask Before You Die

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Willing Wisdom is the first book to offer you a process — 7 Questions to ask, family, friends and charities to help guide giving-decisions. For those who already have a Will, the book helps readers confirm whether their giving decisions continue to feel right.

142 pages, Paperback

Published January 1, 2014

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About the author

Thomas William Deans

6 books2 followers

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Displaying 1 - 4 of 4 reviews
192 reviews15 followers
February 12, 2019
I was given this book by its author, Thomas Deans, following a presentation he gave to a small audience in Vancouver sponsored by an M&A firm and a law firm.

The book provides a framework for starting a conversation with your family about your wealth and how it will be divided or bequeathed, your healthcare directives, and last wishes. I suppose the sponsoring firms were motivated to ‘start a conversation’ with wealthy families about estate planning and other lucrative services.

The 7 questions are:
1. what word best describes our family?
2. describe how your parents acquired their wealth and share a memory about something your parents did to provide for you that left a lasting impression.
3. how would an inheritance advance your dreams for yourself, your family and your community?
4. does fair mean fair or does fair mean equal? who are you planning on leaving your wealth to and will you share a copy of your will with me?
5. describe how your parents divided their assets and when you first learned of the contents of their will. Would you do the same and what would you do differently?
6. describe the role you play or played in the final care of your parents. what was done well and what would you do differently?
7. describe in detail your last wishes.

I didn’t find the questions, or the author's attempt to construct a story around them, particularly thoughtful, as you can intuit from my rating of the book.

But I did glean some nuggets from the book – or at least from listening to Deans’ presentation.
Why should wills be wrapped in a shroud of secrecy? Why not instead approach your death as a family affair – which it inevitably will become – and make your wishes known to those closest to you?

Wealthy parents may worry that their children will choose an easy life if they know they are to receive a large sum, but this isn’t necessarily true. For one, children have a good prima facie sense of their parents’ wealth from how they live and travel. And two, telling your children how your money was earned (assuming legitimately) gives you an opportunity to pass on values alongside the money.

Money is unlikely to precipitate a change in someone’s character; it is more of a catalyst in helping one realize their potential, or conversely, in hastening their demise.

Basically, Deans believes that being totally open with your children about what you have and what they will receive upon your death will help create in your children a healthy relationship to money. It is silence, says Deans, that is the great destroyer of value.

Deans shared his own approach of providing increasingly large and frequent gifts to his children so as to end his life with zero wealth but totally in the care of his children. In this manner he avoids the probate and executor fees as well as the risks of having to manage his wealth in the final stage of cognitive decline.

Deans points out that a third of Canadians and Americans have no will, and among those who do, it's a secret document your loved ones frantically search for after your funeral service. Thus, his call to action is to create a will, update it often, and share it with your loved ones.

There’s a good message there but it comes through way better listening to Deans speak than reading his book.
25 reviews
November 7, 2025
Very good information to consider when thinking and making a will. Definitely a cheesy delivery. But still engaging. Also nice and short which was a plus!
13 reviews
August 25, 2022
Important theme for everyone who posseses anything that will have value after death.
Author 3 books10 followers
July 30, 2013
If you're in the advice business this is an important book. You need to read it and you need to pass on copies to those you work with.

We spend too much time skirting around the issue of death. We don't talk openly and honestly with those who will be affected by our decisions after we die. It's about time a book came out that deals with these issues head on.

Mr. Deans has done an extraordinary job of developing seven common sense questions that a family should answer on an annual basis. The answers to these questions will help you understand what's important for a family and what lessons can be passed on.

I've very lucky in that I grew up in a family that has been following Mr. Dean's advice for years. We regularly have family meetings where we talk about my father's wishes as well as those of us and through us our children. I think this has made death be less of a scary endeavor.

We're all going to die. We don't like to think about death, still it's a fact. This book will provide a platform to start these conversations. The conversations might be uncomfortable at first. I know from first hand experience that over time they become comfortable and important. It's allowed us to have great life lessons for my children.

Buy this book, read it and then pass it on to a friend. Before you pass it on, make sure you write down the 7 questions.
Displaying 1 - 4 of 4 reviews

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