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Reading List

The Northwood Winter Reading List - 2023

Tom McCullough

Given all of the attention lately around AI language models such as ChatGPT, I decided to see if ChatGPT could help write the intro to our winter reading list. Here’s my attempt and entry into ChatGPT: I am the CEO of a family office and would like to provide an overview of the current global state of affairs and key themes heading in 2023.

Here’s the result:

The current global state of affairs is characterized by a complex and rapidly evolving landscape. The COVID-19 pandemic continues to impact the world, leading to ongoing public health and economic challenges, as well as changes in the way people live and work. At the same time, the world is facing a range of other pressing issues, including rising political and social tensions, growing income inequality, and the accelerating impacts of climate change.

Heading into 2023, several key themes are likely to shape the global landscape. One of the most prominent is the ongoing digital transformation, which is rapidly changing the way businesses and individuals operate, communicate, and interact with one another. This is likely to have significant implications for the world of finance and wealth management, as technology continues to play an increasingly important role in shaping investment strategies, managing assets, and delivering financial services.

Another key theme is sustainability and ESG (environmental, social, and governance) investing, as investors become increasingly aware of the importance of considering social and environmental factors when making investment decisions. This trend is likely to continue in 2023 and beyond, as investors seek to align their portfolios with their values and support companies that are taking concrete steps to address pressing social and environmental challenges.    

Finally, the ongoing geopolitical tensions and economic uncertainty are likely to continue to drive investment and market volatility in 2023. As the CEO of a family office, it will be important to remain vigilant and proactive, adapting to changing market conditions and seeking out opportunities to maximize returns while managing risk.

Overall, 2023 is shaping up to be a year of continued change and uncertainty, and it will be important to stay informed and adaptable in order to navigate this rapidly evolving global landscape.

Not bad – obviously quite general, but this technology is still in its infancy, and I am sure will only continue to evolve. I have already heard of a job title called: ChatGPT Prompt Engineer – which is an individual who helps companies feed the correct information into the model to get better and more useful outcomes. Disclosure will be critical – we are going to need to know if what we are reading was written by AI or a human.

But now for some more depth than the “language models” can provide.

Here in Canada, we are back to being more concerned about extreme weather events (i.e., major holiday storms) vs. pandemic restrictions – that’s a good thing! Canada and most of the world continue to grapple with high inflation, rising interest rates and uncertain economic conditions. Last year saw interest rates rise at the fastest pace in a generation and, along with that, many asset values that relied on low rates fell in turn. The tech giants tumbled back down to earth last year and now must show profitability to earn the trust of investors – this is a much more normal investing environment. We were happy to guide our client families through this rapidly shifting market. Over the last few years, it seemed like anyone could be a successful investor. But that shifted in 2022 - it’s not until the tide goes out that you see who’s swimming naked.

The new year always ushers in countless forecasts on what the future will hold. We don’t take these too seriously since most are random and/or wrong. We found this tweet a good take on the forecasting tradition:

Speaking of predictions – former Bank of Canada Governor Stephen Poloz opines in his new book (detailed below) that droves of baby boomers leaving the workforce around the world will keep unemployment low for years to come. If this is the case, retaining employees (especially good ones) will only become more critical this decade. As the Bluenotes article below highlights, in 2019, nearly 60% of employees quit their job because of their boss – so the future of leadership will be kindness. At Northwood, we continue to firmly believe that kindness and empathy are critical for the whole team.     

We’ve curated our latest reading list, including interesting books, articles, and some podcast and streaming options that might interest you. I hope you enjoy the selection of content below and wish you and your family all the best in 2023.

Click on the titles below to see the full content.

Article Recommendations

Oak Tree Capital | Sea Change

Howard Marks reviews the changes we are going through in markets right now – mainly the end of a 40-year period of declining interest rates. Howard believes we are witnessing a complete reversal of the conditions of the last 13 years (2009-2021).

The Atlantic | The College Essay is Dead

Keeping with the ChatGPT hype, this article raises concerns about the potential for AI-generated essays to be used for academic dishonesty and the impact on students' critical thinking skills.

LinkedIn News | 41 Big Ideas that will change our world in 2023

This list has been highlighted in previous reading lists, but we continue to enjoy it each year!

Medium | How to be an effective early-stage employee, Hint: be helpful.

This article details The Helpful Hierarchy, which is a great guide for anyone starting out or looking to advance their career. Pass it on to a young person you know.  

New York Times | The Great Delusion Behind Twitter  

This opinion piece challenges the assumption that Twitter needs to be the world’s town square.    

The Atlantic | Despite Everything You Think You Know, America Is on the Right Track  

America is deeply negative today, but this article argues that the case for optimism is surprisingly strong.

Bluenotes | The future of leadership is kindness

The title says it all.

The Guardian | Why Is So Little Known About the 1930s Coup Attempt Against FDR?

I had no idea about this coup attempt against FDR. This article questions why there is limited information and discussion around the event.  

Politico | Where Will This Political Violence Lead? Look to the 1850s.    

This article argues the current political divisions in the US are like those of the 1850s.

The Atlantic | The Lionel Messi Guide to Living

An uplifting piece about Lionel Messi demonstrating to a world fixated on youth the stunning possibility of a triumph in the latter stages of a career.

Book Recommendations

Van Gogh: The Life | Gregory White Smith and Steven Naifeh

Extremely well written and eminently readable, this deep dive into the troubled and complicated life of one of the world’s most renowned painters is a tour de force.   

Small Things Like These | Claire Keegan

Very short book about tenderness, community, knowing too much, and difficult choices in 1985 Ireland. It’s a beautiful read. As one of the endorsements on the book cover says - it’s “a book that makes you excited to discover everything its author has ever written…”.

I Am Enough | Danielle Saputo

This is a very personal journey story of a young girl in a really rich, male dominated, complicated family.

The Next Age of Uncertainty | Stephen Poloz

The former Governor of the Bank of Canada has an interesting take on the shifting economic landscape. He dives into the forces shaping the future: aging workforce, mounting debt, rising income inequality, technological advances, and climate change.

The Defining Decade: Why Your Twenties Matter - and How to Make the Most of Them Now | Meg Jay

Meg Jay debunks current cultural thinking around the twenty-something years. Sharing what various experts know about the unique power of our twenties and how they shape our lives. A good Next Gen recommendation.

Northwood’s own Scott Dickenson’s 2022 Reading List (10 Books)  

Reader Suggestions:

The History of Socialism and Capitalism | Niall Ferguson and Victor Davis Hanson

A great read which dives into how by the 1980s socialism had largely failed, but there is a    strong revival of interest in socialism among young people today (but they see it in a different light).

The Revenge of Power: How Autocrats Are Reinventing Politics for the 21st Century | Moisés Naím's  

The rise of autocracy and the related loss of freedoms may be the single biggest issue facing the world. This book draws out the ugly state of the political world today.

As a lifelong learner, I am always interested in reading or listening to material that broadens my horizons, challenges my thinking, and provides all-important context for the decisions we make. This is true for the entire Northwood team.

We’d also be interested in hearing what you’ve been reading or listening to lately. If you’ve come across any particularly insightful books, articles, shows, or podcasts, please feel free to send them to me at Thanks to the many people who have already shared their ideas.    

All the best,  




Tom McCullough

Tom McCullough is Chairman and CEO of Northwood Family Office. The combination of his background, along with his own family’s desire for a truly ‘comprehensive, customized and confidential service, led him on a search for a multi-family office. Tom is a frequent speaker on issues relevant to families of wealth and is the co-author of Wealth of Wisdom: The Top 50 Questions Wealthy Families Ask and Family Wealth Management: Imperatives for Successful Investing in the New World Order and the soon-to-be-released Wealth of Wisdom: Top Practices for Wealthy Families and Their Advisors. He is an adjunct professor and Executive-in-Residence at the University of Toronto’s Rotman School of Management MBA program. He is an Entrepreneur-in-Residence at Western University’s Ivey School of Business and a member of the Editorial Board of the Journal of Wealth Management. He was recently awarded ‘Best Individual Contribution to Thought Leadership in the Wealth Management Industry’ by the 2020 Family Wealth Report Awards.

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