The Perspective Blog
Reading List

The Northwood 2025 Fall Reading List

BY
Brad Jesson

We are witnessing dramatic shifts in the world today, much of which is being driven by the US. Tariffs are at their highest levels since the 1930s, more immigrants are being detained than at any point in recent decades, several government agencies have been publicly undermined, and new legislation is set to further increase the national debt – all of which represents a partial list. We are witnessing a fundamental shift south of the border.

At the same time, AI is advancing faster than most people can grasp, reshaping industries, jobs, and even how we define creativity and truth. Many see it not as just another technology cycle, but as a fundamental shift driven by rapid adoption, massive capital investment, and the rise of intelligence as core infrastructure. Yet, as one podcast below argues, the AI revolution may unfold more slowly and unevenly than current narratives suggest.

Market dynamics are also tilting under the weight of passive investing and unprecedented debt levels. Families are asking deeper questions about resilience, freedom, and the next generation’s relationship with technology. Health, attention, and optimism are increasingly recognized as essential resources to nurture.

And yet, amid it all, there is a return to what endures: the timeless value of judgment, simplicity, and stewardship. These are qualities that do not fluctuate with markets or political cycles, and many of the readings below touch on them.

This fall’s reading list explores these tensions. From essays on corruption and autocracy to reflections on boredom, happiness, and legacy, each selection offers a reminder that wisdom, not noise, is what compounds over time.

As always, we’ve curated a mix of books, articles, and thought-provoking content we think you’ll enjoy.

Happy reading,

The Northwood Team

Click on the titles below to see the full content.

Article Recommendations

America’s Coming Crash: Will Washington’s Debt Addiction Spark the Next Global Crisis? Foreign Affairs

The writer warns that ballooning U.S. debt could trigger the next global financial reckoning, a sober reminder that fiscal prudence and political courage are intertwined.

America Has Never Seen Corruption Like Trump’s The Atlantic

A look at how corruption erodes institutions, and how power without accountability can redefine democracy itself.

The Rise and Potential Cost of Passive InvestingSpence Abraham Substack

A thoughtful examination of how passive investing’s dominance could distort markets and investor behaviour.

America Needs a Mass Movement—Now  The Atlantic

On the rise of authoritarian movements and the fragile power of social resistance in democracies under strain.

The (Uncertain) Payoff from Alternative Investments Aswath Damodaran Blog

A data-driven take on what’s hype and what’s durable in the world of private assets and alternatives.

What Kids Told Us About How to Get Them Off Their Phones The Atlantic

Jonathan Haidt expands on The Anxious Generation book(a great read!) exploring how screen time reshapes independence, resilience,and childhood.

ChatGPT May Be Eroding Critical Thinking Skills TIME

A snapshot of how AI is already transforming classrooms and what it means for human learning.

Is Modern Life Fueling a Rise in Cancer Among Millennials?The Washington Post

A haunting, data-rich investigation into the unintended health consequences of modernity.

‘Profound and Abiding Rage’: Canada’s Answer to America’s Abandonment The New York Times

A deep dive into Canada’s break from U.S. integration, spurred by tariffs, annexation talk, and a new era of nationalism.

Simple Investments, Complex Investors Cape May Wealth

On why simplicity - not complexity - often drives the best long-term outcomes.

You Need to Be Bored (Here’s Why)Harvard Business Review

A reminder that attention is the true scarce resource in modern life (not time).

The dawn of the post-literate society - Cultural Capital

A provocative essay on how screens, algorithms, and cognitive shortcuts may be ushering in an era where deep reading and the civilization it sustained faces existential decline.

Book Recommendations

Big Ideas & Bold Thinking

The Creative Act: A Way of Being by Rick Rubin

A meditation on creativity, presence, and process - equally relevant to art, leadership, and life.

Liquid Life by Zygmunt Bauman

A philosophical look at modernity’s constant motion (the crazy pace of life today), and the challenge of building lasting meaning in fluid times.

Thinking in Bets by Annie Duke

How probabilistic thinking can improve decision-making in investing, business, and beyond.

Playing to Win by A.G. Lafley & Roger Martin

A classic on strategy, choice, and execution, a must-read for anyone leading in complexity.

History & Global Affairs

The Looming Tower by Lawrence Wright

A riveting historical narrative about ideology, intelligence, and the consequences of power.

Fiction: Literary & Historical

Circle of Days by Ken Follett

A sweeping historical novel set in Neolithic Britain, imagining the human drama behind Stonehenge’s creation—ambition, rivalry, and survival in a world striving for permanence.

This Is Happiness by Niall Williams

A lyrical portrait of rural Ireland on the brink of modernity, where the arrival of electricity sparks a tender story of love, memory, and the quiet magic of everyday life.

The Doorman by Chris Pavone

A taut, character-driven thriller set in a Manhattan high-rise, exposing privilege and secrets as one doorman faces a night of reckoning amid protests and hidden agendas.

Broken Country by Clare Leslie Hall

A haunting, multi-generational drama of love and betrayal in rural England, where buried secrets and rekindled passions unravel into tragedy and hard truths.

Parenting & Personal Finance

Raising Financially Fit Kids by Joline Godfrey

A timeless guide for parents seeking to instill healthy money values and independence.

Get Out of My Life, But First Could You Drive Me & Cheryl to the Mall? by Anthony Wolf

A sharp, funny, and compassionate look at parenting teens in the age of independence.

Legacy & Life Stories

The Cycle of the Gift by James E. Hughes Jr., Susan Massenzio, Keith Whitaker

Explores the art of thoughtful giving and how families can sustain wealth and values across generations.

The Essential Questions: Interview Your Family to Uncover Stories and Bridge Generations by Elizabeth Keating Jr.

A practical guide to capturing family stories and creating meaningful connections across generations.

Podcast & Conversation Recommendations

Calm Parenting Podcast #530: 7 Favorite Ideas for Sleep, Anxiety, Meltdowns, School, Homework & Impulsivity

Simple, compassionate tools for parents navigating an overstimulated world.

Dwarkesh Patel: Why I don’t think AGI is right around the corner (June 2025)

Interesting take on the potential speed of AI.

Tim Ferriss Show: John Arnold on Systems Thinking, Altruism, and Money

The billionaire philanthropist shares hard-earned lessons on wealth, impact, and reform.

Speaking of Psychology: Why Our Attention Spans Are Shrinking

A psychological look at how digital life fragments focus, and what we can do to reclaim it.

Other

How To Be A Better Reader (Do This To Your Books)

A good video on how to be a better reader!

As lifelong learners, we are always interested in reading or listening to material that broadens our horizons, challenges our thinking, and provides an 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 us at tm@northwoodfamilyoffice.com, bcj@northwoodfamilyoffice.com or sd@northwoodfamilyoffice.com.

Thanks to the many people who have already shared their ideas.

All the best,

Northwood Team

1
2
3
4

Brad Jesson

Brad is a member of Northwood’s family office advisory group, working with families in the areas of goals based financial planning, investment management, tax planning, and next-generation education. In addition to his work with families, Brad is actively involved with Northwood next generation education and regularly contributes to Northwood's Thought Leadership Newsletter.

Read More