The Perspective Blog
Wealth of Wisdom Chapter Summary: Learning from Your Money History and Writing a New Story
For regular subscribers to Northwood’s quarterly newsletter, you’ll know that Northwood’s Chairman and CEO Tom McCullough has launched his second book in the Wealth of Wisdom series -- Wealth of Wisdom: Top Practices for Wealthy Families and Their Advisors alongside his co-editor Keith Whitaker.
This time around, Tom and Keith drew upon the experience of more than 60 experts who work with families of wealth by asking them to share practical tools, exercises, techniques, templates, and strategies that can be immediately applied by wealthy families and their advisors. The resulting book provides a practical overview through short chapters that can be read independently, allowing readers to focus on the practices and tools that are of interest to them.
Chapter 9 of the book, Learning from Your Money History and Writing a New Story, and is authored by Jill Shipley who specializes in family dynamics and governance.
Jill discusses the unconscious drivers that impact our actions and attitude. No matter how much or how little money was spoken about in someone’s household as a child, we all grow up with certain experiences, messages, and stereotypes or stigmas related to money. These in turn play a role to define our attitudes, biases, emotions and behaviours related to money which we often carry into adulthood.
Issues arise when these factors from our “money history” produce negative emotions or behaviours surrounding money, even when they are no longer useful or relevant to our financial circumstances. Since these factors are often unconscious, Jill suggests a four-step process to guide families through an exercise to explore and unpack their money history, and to work towards creating a new relationship to money. A condensed version is presented here so readers can use the process to reflect on their own money history.
1. Exploring Your Attitudes and Biases about Wealth
- Consider the words that come to mind when you think of wealth or people who are wealthy from the list below. Note which ones have a positive, negative, or neutral connotation.

2. Look Back to Be Able to Move Forward
Write down your answers to the following questions:
While you were growing up…
- What were the messages you heard about money?
- What were the financial circumstances of your parents’ own childhoods and how could that have shaped their own money stories?
- How did you learn about the value of a dollar, and what were your habits when you received money (save, spend, give)?
3. Reflect on Your Relationship with Money Today
Consider how the lessons you learned about money growing up affect you today by answering the following questions:
- How does your money history impact how you behave and feel about money today out of the following list:

In what way does your current behaviour align and differ from your money history and the messages you received growing up?
4. Writing a New Story
Think about the relationship you want to have with money. Although you may find some of the aspects of your money history are aligned with your values, there are likely some others that are not serving you well today.
Reflect on the below questions to re-orient yourself and start working towards creating a new money history going forward:
- What are the lessons you want to pass on to your children or future generations?
- Are your current practices helping or hindering you from achieving your ideal relationship with money?
- What will you do more of, do better, or do differently/less of to achieve your ideal new money story?
The author ends the chapter with a discussion of a real-life example of a client who participated in this exercise. This client couple sold a business for over $100M but found themselves worried that they would run out of money despite spending very frugally. They also experienced guilt surrounding their wealth, leading them to give handouts to those around them and subsequently question whether these relationships were genuine. After completing the above exercise, they decided to dedicate themselves to philanthropy and impact investing, and to start developing a mindset of abundance rather than scarcity to better channel their thinking surrounding their wealth.
This chapter is a great read and the exercise can be applied to families of any background or level of wealth. If you’re interested in reading the full chapter, or other sections of the book, it can be found on Amazon here, or you can listen to the Wealth of Wisdom podcasts soon to be recorded with the author Jill Shipley.