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Thirteen more books highly recommended by family advisors

These page-turners gave their careers a boost, motivated them or just made them happy

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For advisors of wealthy families, staying on top of this quickly evolving field is vital to success. Following the high readership of our first two book-recommendation lists (find them here and here), we’re back with the third in the series.

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In this mix of new and old you’ll find books about managing time effectively, understanding the psychology of wealth and exploring ways to simplify your life and be happier.

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Cindy Radu, independent family wealth transition advisor, Calgary

  • The Gift of Lift: Harnessing the Power of Stewardship to Elevate the World (by David R. York): “Hot off the press, this book will quickly become a go-to resource for anyone interested in the concept of stewardship, which is integral to cultivating family wealth legacies. York takes the reader into the mindset of a steward, fully invested in purpose, passion, freedom and community engagement while transcending boundaries to something bigger than themselves. Drawing on examples from Cincinnatus, George Washington, Nelson Mandela and — my personal favorite — Horton of Horton Hears a Who!, this book explores how anyone can choose to embrace a perspective of stewardship through their own unique expression of commonalities that all stewards share.”
  • Flourish: A Visionary New Understanding of Happiness and Well-being (by Martin E.P. Seligman): “I was introduced to this book through the Purposeful Planning Institute, a multidisciplinary group of professionals who want to serve the families they work with in deeper and more positive ways. The author of Flourish, a research scientist in the field of positive psychology, identifies flourishing as ‘the gold standard for measuring well-being.’ Well-being theory posits five elements that contribute to well-being as captured by the mnemonic PERMA: Positive emotion, Engagement, positive Relationships, Meaning and Accomplishment. This guidebook offers exercises to create happiness and teach well-being to young people, and it includes five chapters on ways to flourish. While it’s not a light read (says the former tax lawyer), with all that is going on in the world today, consider investing the time to learn about happiness, flourishing and well-being.”
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Matt Fullbrook, governance advisor and researcher, podcaster and executive-in-residence at the Rotman School of Management, University of Toronto

  • Thing Explainer: Complicated Stuff in Simple Words (by Randall Munroe): “I’ve gifted this book more times than I can count. It’s perhaps the most valuable book about communication, management and human behaviour that I’ve ever read — and it’s not even about those things. In his introduction, Randall Munroe explains, ‘I’ve spent a lot of my life worried that people will think I don’t know enough. Sometimes, that worry has made me use big words when I don’t need to.’ Sound familiar? Yeah, me too. Thing Explainer is like an illustrated encyclopedia that describes 45 complex things using only cool diagrams and the 1,000 most common words in the English language. You’ll learn about a nuclear reactor (heavy metal power building), animal cells (tiny bags of water you’re made of) and hospital beds (room for helping people) in just a few minutes without needing to learn new words or feel inadequate. I bet you could explain all the complex parts of your family office with simpler words, too.”
  • Range: Why Generalists Triumph in a Specialized World (by David Epstein): “What is expertise? What’s the best way to become an expert in something? How much does expertise help us and our organizations? The answers to these questions are probably not what you expect. In Range, David Epstein synthesizes a huge amount of scientific and practical evidence about the nature of expertise into a massively myth-busting book that really helped me to rethink how to deploy my current expertise effectively and how best to acquire new skills. The insights here will help you to ask better questions, surround yourself with better people, and get the most out of your ongoing education and development.”
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Jen Lawrence, master life coach, divorce coach, Process Design Consultants Inc., Oakville, Ont., and author of Engage the Fox: A Business Fable About Thinking Critically and Motivating Your Team

  • Decolonizing Wealth: Indigenous Wisdom to Heal Divides and Restore Balance (by Edgar Villanueva): “A thought-provoking text exploring the impact of colonialism on finance and philanthropy and how healing can begin after money has been used as a tool of oppression. Villanueva, a member of the Lumbee Nation, has a unique view of wealth as one of the few Indigenous senior philanthropy professionals in the United States. Villanueva posits that money can be used as medicine and invites the reader into the healing circle. The book outlines the seven steps to healing that can be applied at an individual or institutional level. This book is particularly useful for family office professionals who want to offer a different perspective to G2 or G3 clients who are uncomfortable with the origins of their wealth. It called me to challenge my own privilege as a professional working in this space and reframe money as a powerful healing tool.”
  • Time Smart: How to Reclaim Your Time and Live a Happier Life (by Ashley Whillans): “In this book, Harvard Business School professor Ashley Whillans focuses on ‘time affluence,’ recognizing that many people, including high-net-worth individuals, feel time-poor. Time poverty can lead to less joy, poor health, lower productivity and even divorce. Whillans not only outlines the theory around building time affluence but offers a number of practical guidelines for creating more time in your schedule. Whether you are a time-deprived family-office professional or have clients who could benefit, this is a quick and productive read. I’ve found myself employing many techniques suggested and am already freeing up more time for things I enjoy.”
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Brad Jesson, principal, client service, Northwood Family Office, Toronto

  • Complete Family Wealth: Wealth as Well-Being (James E. Hughes Jr., Susan E. Massenzio, Keith Whitaker): “This is the best one-stop reference for ensuring a positive legacy for future generations. The authors succinctly break out family wealth into five forms — human, intellectual, social, spiritual, and financial — and explore specific practices around each. The book provides insightful examples from real families struggling with familiar family wealth challenges.”
  • Upstream: The Quest to Solve Problems Before They Happen (by Dan Heath): “Two friends are out camping. They hear a cry for help and rush into a fast-flowing stream to save a drowning child … only to see another struggling child drift by … and then another, and another. As one of the campers starts to run to shore, his incredulous friend demands to know where he is going. Over his shoulder he yells, ‘I’m going upstream to tackle the guy who is throwing all these kids in the water.’” This story in Upstream made me consider how the focus on prevention versus reaction is the key to success for wealth holders in a market downdraft like the one we are currently in. Drawing on insights from hundreds of great interviews, Upstream explores how to prevent problems before they happen. Dan Heath is a great business writer, and if you haven’t read it, Dan and Chip Heath’s Made to Stick is also a fantastic read.”
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Christopher Singh Gandhu, partner and family office leader, KPMG Canada, Calgary

  • The Psychology of Money: Timeless Lessons on Wealth, Greed, and Happiness (by Morgan Housel): “Wealth strategy and investment management are front and centre for our families. This book does a fantastic job of explaining the psychology behind investing. In my decade-long tenure I have observed how many families made decisions based on feelings, gut and impulse rather than relying solely on objective criterion or data. Understanding our own biases, blind spots and investing tendencies is as important as any finance text. This book is as impactful for families as it is for their advisors.”
  • The Promise (by Damon Galgut): “This historical fiction novel, narrating the story of two generations of a South African family, is a fabulous read and well deserving of its 2021 Booker Prize win. From an advisor’s perspective, what is immensely interesting are the family dynamics at play between the mom and dad, the parents and their children, and between the siblings. Specifically, estate planning, documenting testamentary intentions in appropriate documents and the impact of interpersonal dynamics on the course of a family’s future are neatly intertwined in the story — ready for astute readers to parse and appreciate.”
For more about HNW wealth management,
family businesses, philanthropy and estate
planning, visit Canadian Family Offices.

Steve Legler, coach, facilitator and family legacy guide, Montreal, and author of Interdependent Wealth: How Family Systems Theory Illuminates Successful Intergenerational Wealth Transitions

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  • Enabling Next Generation Legacies: 35 Questions That Next Generation Members in Enterprising Families Ask (by Peter Jaskiewicz and Sabine B. Rau): “Peter Jaskiewicz was born into a family business in Poland that fell apart because of relationship issues, which inspired him to do his PhD on the reasons why families stay together or fall apart. In this book he crowdsourced internationally from members of enterprising families to come up with 35 questions that they would like to ask senior business leaders. Responses from a wide variety of academic family and business scholars led to the 35 chapters in the book, along with personal anecdotes. When you can use an example from a family in a book, it can be a great conversation starter, and it lets families draw parallels to their own family. The biggest problem with having conversations is getting them started.”
  • The Gift of Lift: Harnessing the Power of Stewardship to Elevate the World (by David R. York): “The author is a lawyer who began his career on the structural side of estate planning, designing trusts and writing wills. He quickly realized that this was missing a key need: families need to discuss things first. Using what he learned from working with wealthy family clients, he writes about the importance of instilling the idea of stewardship in rising generations. It’s a powerful idea, and he writes that if more people in the world adopted a stewardship perspective in the way they interacted with the world, the world would be a better place. One example he gives is the story of a client in Salt Lake City who bought the basketball team the Utah Jazz to save them from having to leave the state. But instead of owning the team, the family made a benevolent move to restructure it. Once it was profitable, they created a trust so that the entire community owned the team.”
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Recommended from Editorial
  1. Family office executives, clockwise from upper left: Douglas Byblow, Chris Clarke, Éric Lapointe, Arthur Salzer, Scott Dickenson, Gregory Moore.
    Six Canadian family-office leaders and the books that energized them
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    Six more Canadian family-office leaders and books that inspired them

Richard Leon, partner, portfolio manager, Richter Family Office, Montreal

  • Winning Ugly: Mental Warfare in Tennis — Lessons From a Master (by Brad Gilbert and Steve Jamison): “Pro tennis player Brad Gilbert explains how preparation for matches gave him an edge and helped him achieve results above his natural ability. He mapped out game plans for each opponent; he knew how to play to his own strengths and his opponents’ weaknesses; and he was flexible enough to change strategy midgame, reacting to conditions as they changed. His mental strength made him frustrating to play against. This book resonated with me, as many of the lessons translate from sport to the business and family office fields. Because preparation is a large part of what we do, staying focused and cool with a flexible approach to changing conditions makes me better prepared to deal with things that are out of my control.”
  • Reading for relaxation: medieval history: “With a goal of good work-life balance, I don’t want to go home and read more broker reports and financial statements — the markets are never closed — so it’s nice to have a distraction. I was always an avid reader and I studied medieval history, and so I’m drawn to history and fiction because it’s completely removed from all-consuming work. Reading about history is a good icebreaker and distraction from the intensity of markets and trading. The Magna Carta, the history of England and France, Chaucer and Shakespeare, that’s what always appealed to me.”

Responses have been edited for clarity and brevity.

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