Reading list
What I read, and what I'd have you read.
A working list of the books that have shaped how I think about money, leadership, and the long view. Not a syllabus. A starting point. Filter by theme. The “Start here” pick in each category is the one to open first.
The Richest Man in Babylon
George S. Clason
finance
Start hereThe Richest Man in Babylon
George S. Clason
Old parables, simple rules. If nobody ever sat you down and explained how to keep what you earn, start here. Thirty minutes a chapter, the arithmetic of a lifetime.
Find it on Amazon →
The Psychology of Money
Morgan Housel
finance
№ 02The Psychology of Money
Morgan Housel
Behavioural finance, short chapters. Explains why sensible people make unsensible money decisions. Pairs well with Babylon.
Find it on Amazon →
The Little Book of Common Sense Investing
John C. Bogle
finance
№ 03The Little Book of Common Sense Investing
John C. Bogle
The case for low-cost index investing from the man who built Vanguard. If you can only take one lesson on investing, take this one.
Find it on Amazon →
A Random Walk Down Wall Street
Burton G. Malkiel
finance
№ 04A Random Walk Down Wall Street
Burton G. Malkiel
The best primer on how markets actually behave, written for someone who has never bought a share. Malkiel is patient, sceptical, and clear.
Find it on Amazon →
The Intelligent Investor
Benjamin Graham
finance
№ 05The Intelligent Investor
Benjamin Graham
The book Warren Buffett credits. Dense but serious. Read it once you are comfortable with the basics; the distinction between investing and speculating will stay with you.
Find it on Amazon →
One Up On Wall Street
Peter Lynch
finance
№ 06One Up On Wall Street
Peter Lynch
Lynch managed the Magellan fund during its best run. His advice on doing your own research and trusting what you can see is an antidote to financial noise.
Find it on Amazon →
Your Money or Your Life
Vicki Robin and Joe Dominguez
finance
№ 07Your Money or Your Life
Vicki Robin and Joe Dominguez
Reframes income in terms of the hours of life you traded for it. Changes how you look at every future purchase.
Find it on Amazon →
The Millionaire Next Door
Thomas J. Stanley and William D. Danko
finance
№ 08The Millionaire Next Door
Thomas J. Stanley and William D. Danko
A study of who actually accumulates wealth in the United States. The answer is not who you expect, and the habits are replicable.
Find it on Amazon →
The Simple Path to Wealth
JL Collins
finance
№ 09The Simple Path to Wealth
JL Collins
Originally a series of letters from a father to his daughter. The warmest, most practical book on long-horizon investing I have come across.
Find it on Amazon →
Die with Zero
Bill Perkins
finance
№ 10Die with Zero
Bill Perkins
Provocative counterweight to the saving-forever books above. Forces you to think about what money is actually for. Read it last.
Find it on Amazon →
Poor Economics
Abhijit V. Banerjee and Esther Duflo
economics
Start herePoor Economics
Abhijit V. Banerjee and Esther Duflo
Development economics anchored in field experiments rather than theory. The Caribbean reader will recognise many of the questions. A good starting point for understanding how evidence changes policy.
Find it on Amazon →
The Undercover Economist
Tim Harford
economics
№ 02The Undercover Economist
Tim Harford
Makes price theory visible in everyday life. Trains the eye to spot incentives in ordinary situations.
Find it on Amazon →
Economics: The User’s Guide
Ha-Joon Chang
economics
№ 03Economics: The User’s Guide
Ha-Joon Chang
A heterodox introduction. Shows that there is not one economics but several, and that which one you choose shapes what policies you think are possible.
Find it on Amazon →
Why Nations Fail
Daron Acemoglu and James A. Robinson
economics
№ 04Why Nations Fail
Daron Acemoglu and James A. Robinson
Institutions, not geography, explain why some economies thrive and others stagnate. Uncomfortable reading for anyone who thinks the Caribbean’s problems are only external.
Find it on Amazon →
Development as Freedom
Amartya Sen
economics
№ 05Development as Freedom
Amartya Sen
Sen redefines development as the expansion of human freedoms rather than the growth of GDP. The most useful lens I know for small-state policy work.
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Globalisation and Its Discontents
Joseph E. Stiglitz
economics
№ 06Globalisation and Its Discontents
Joseph E. Stiglitz
An insider’s account of the IMF, the World Bank, and the 1990s debt crises. The Caribbean lived through the follow-on. Stiglitz names the players.
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Doughnut Economics
Kate Raworth
economics
№ 07Doughnut Economics
Kate Raworth
A framework for thinking about economies that sit inside ecological and social limits. Particularly useful for SIDS policy.
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Capital in the Twenty-First Century
Thomas Piketty
economics
№ 08Capital in the Twenty-First Century
Thomas Piketty
The central dataset of modern inequality research. Not a short read, but the r > g idea is essential context for any conversation on wealth concentration.
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The Mystery of Capital
Hernando de Soto
economics
№ 09The Mystery of Capital
Hernando de Soto
Why dead capital sits in informal property across the developing world, and what formal title would unlock. Directly relevant to Caribbean land policy.
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The Great Escape
Angus Deaton
economics
№ 10The Great Escape
Angus Deaton
Deaton’s history of health, wealth, and inequality across the long run. A humane counterpoint to pessimism about development.
Find it on Amazon →
Start with Why
Simon Sinek
leadership
Start hereStart with Why
Simon Sinek
Institutions and leaders who articulate their purpose first outperform those who lead with product or process. Useful in the Caribbean context because our public bodies often skip that step.
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Leaders Eat Last
Simon Sinek
leadership
№ 02Leaders Eat Last
Simon Sinek
The follow-up to Start with Why. On creating the kind of team environment where people genuinely look out for each other, and why that produces better work.
Find it on Amazon →
The 7 Habits of Highly Effective People
Stephen R. Covey
leadership
№ 03The 7 Habits of Highly Effective People
Stephen R. Covey
Unfashionable to recommend, still worth the read. The distinction between urgent and important is the single idea that will save you the most time over a career.
Find it on Amazon →
Dare to Lead
Brené Brown
leadership
№ 04Dare to Lead
Brené Brown
On leading with clarity about values, and on the role of vulnerability in leadership that lasts. Practical, not sentimental.
Find it on Amazon →
Extreme Ownership
Jocko Willink and Leif Babin
leadership
№ 05Extreme Ownership
Jocko Willink and Leif Babin
Two former Navy SEALs on the discipline of taking responsibility for everything inside your remit. Less about military tactics, more about how adults run teams.
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Drive
Daniel H. Pink
leadership
№ 06Drive
Daniel H. Pink
The evidence on what actually motivates people beyond money. If you lead anyone other than yourself, read this before the next performance review.
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Principles
Ray Dalio
leadership
№ 07Principles
Ray Dalio
Dalio’s operating manual for Bridgewater. Long, occasionally eccentric, full of hard-won rules for how to make decisions under uncertainty.
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Multipliers
Liz Wiseman
leadership
№ 08Multipliers
Liz Wiseman
Why some leaders draw double the intelligence out of a team and others drain it. A useful mirror for anyone who runs meetings.
Find it on Amazon →
The Hard Thing About Hard Things
Ben Horowitz
leadership
№ 09The Hard Thing About Hard Things
Ben Horowitz
Horowitz built and sold a company, nearly twice. The chapters on decisions you hope never to face are the most honest writing on leadership I have read.
Find it on Amazon →
Tribal Leadership
Dave Logan, John King, and Halee Fischer-Wright
leadership
№ 10Tribal Leadership
Dave Logan, John King, and Halee Fischer-Wright
A five-stage model for where a culture sits and what moves it forward. Useful for anyone stepping into a team that has been underperforming for years.
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Good to Great
Jim Collins
strategy
Start hereGood to Great
Jim Collins
A study of what separates durable organisations from merely successful ones. The discipline of confronting the brutal facts is the chapter that stays with me.
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Built to Last
Jim Collins and Jerry I. Porras
strategy
№ 02Built to Last
Jim Collins and Jerry I. Porras
The prequel to Good to Great. On the shared habits of companies that outlast their founders by a century or more.
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Playing to Win
A.G. Lafley and Roger L. Martin
strategy
№ 03Playing to Win
A.G. Lafley and Roger L. Martin
Five clean questions that force real strategic choices. Written by the former CEO of P&G. Compact, direct, and used in boardrooms worldwide.
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The Innovator’s Dilemma
Clayton M. Christensen
strategy
№ 04The Innovator’s Dilemma
Clayton M. Christensen
Why good companies fail even when they do everything right. Essential reading for anyone running a Caribbean business watching tech shift underneath it.
Find it on Amazon →
Blue Ocean Strategy
W. Chan Kim and Renée Mauborgne
strategy
№ 05Blue Ocean Strategy
W. Chan Kim and Renée Mauborgne
On the discipline of competing where competition is weakest. Tourism operators across the region would benefit from reading this twice.
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Zero to One
Peter Thiel with Blake Masters
strategy
№ 06Zero to One
Peter Thiel with Blake Masters
Contrarian, sharp, occasionally wrong, always worth arguing with. On how new things actually get built.
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Thinking in Systems
Donella H. Meadows
strategy
№ 07Thinking in Systems
Donella H. Meadows
The single best short introduction to systems thinking. Once you see feedback loops, you see them everywhere.
Find it on Amazon →
Competitive Strategy
Michael E. Porter
strategy
№ 08Competitive Strategy
Michael E. Porter
The textbook. Porter’s five forces framework still structures how the world analyses industry competition. Denser than the others here.
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The Art of War
Sun Tzu
strategy
№ 09The Art of War
Sun Tzu
Short, old, endlessly re-readable. The chapters on terrain and timing translate directly into business and political strategy, if you let them.
Find it on Amazon →
Seven Powers
Hamilton Helmer
strategy
№ 10Seven Powers
Hamilton Helmer
A precise taxonomy of the only seven durable competitive advantages. Useful once you want sharper language for the strategy you already intuit.
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Meditations
Marcus Aurelius
philosophy
Start hereMeditations
Marcus Aurelius
A working ruler’s notebook, written without any intention of publication. The entries on attention, duty, and accepting what you cannot control have aged better than most modern self-help.
Find it on Amazon →
Letters from a Stoic
Seneca
philosophy
№ 02Letters from a Stoic
Seneca
Seneca’s letters to Lucilius. Practical Stoicism in small doses, easier to digest than the Meditations if you are new to the school.
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A Guide to the Good Life
William B. Irvine
philosophy
№ 03A Guide to the Good Life
William B. Irvine
Modern translation of Stoic practice. A fair bridge between the ancient texts and how to actually live with them in 2026.
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Enchiridion
Epictetus
philosophy
№ 04Enchiridion
Epictetus
A short handbook of core principles, written down by Epictetus’ student. Read in an afternoon; re-read for life.
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The Obstacle Is the Way
Ryan Holiday
philosophy
№ 05The Obstacle Is the Way
Ryan Holiday
Stoicism in the language of modern work and sport. Short chapters, examples from business and history. A helpful primer if the ancient texts feel remote.
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Ego Is the Enemy
Ryan Holiday
philosophy
№ 06Ego Is the Enemy
Ryan Holiday
Holiday’s strongest book. A case against self-importance in three stages: aspiration, success, failure. A useful mirror for anyone building a public profile.
Find it on Amazon →
Tao Te Ching
Laozi (Lao Tzu)
philosophy
№ 07Tao Te Ching
Laozi (Lao Tzu)
The foundational Taoist text. Eighty-one short verses on restraint, yielding, and the limits of effort. A counterweight to Stoicism’s active cast.
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On the Shortness of Life
Seneca
philosophy
№ 08On the Shortness of Life
Seneca
A short essay that lands harder every decade you read it. On how people squander time on the wrong things and call it being busy.
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The Consolation of Philosophy
Boethius
philosophy
№ 09The Consolation of Philosophy
Boethius
Written in prison, awaiting execution. Boethius builds a conversation with Philosophy herself about fortune and virtue. Quiet, tough, beautiful.
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Walden
Henry David Thoreau
philosophy
№ 10Walden
Henry David Thoreau
On what it means to live deliberately. Uneven in places, but the passages that land will follow you for years.
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From Columbus to Castro
Eric Williams
caribbean
Start hereFrom Columbus to Castro
Eric Williams
The foundational economic history of the Caribbean, written by a Caribbean economist who became a prime minister. Essential for understanding why our fiscal choices look the way they do.
Find it on Amazon →
Capitalism and Slavery
Eric Williams
caribbean
№ 02Capitalism and Slavery
Eric Williams
Williams’ doctoral thesis. The argument that the British industrial revolution was funded by Caribbean slave labour is no longer controversial. It was when he wrote it.
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The Black Jacobins
C. L. R. James
caribbean
№ 03The Black Jacobins
C. L. R. James
The story of the Haitian Revolution, still the only successful slave revolt in history. James writes with the pace of a novelist and the rigour of a historian.
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How Europe Underdeveloped Africa
Walter Rodney
caribbean
№ 04How Europe Underdeveloped Africa
Walter Rodney
A Guyanese historian’s case for why Africa was deliberately structured for extraction. The argument travels directly to the Caribbean.
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A Small Place
Jamaica Kincaid
caribbean
№ 05A Small Place
Jamaica Kincaid
A long essay on Antigua, tourism, and the ways colonial inheritance shows up in the ordinary. The best 80 pages on how the Caribbean is consumed.
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The Lonely Londoners
Sam Selvon
caribbean
№ 06The Lonely Londoners
Sam Selvon
The Windrush novel. Selvon writes the interior life of the post-war Caribbean migrant to London in a creole prose nobody had put on the page before.
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Beyond a Boundary
C. L. R. James
caribbean
№ 07Beyond a Boundary
C. L. R. James
A book ostensibly about cricket that is really about empire, race, and the meaning of a colonial education. Reads like nothing else in Caribbean letters.
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The Wretched of the Earth
Frantz Fanon
caribbean
№ 08The Wretched of the Earth
Frantz Fanon
Written by a Martinican psychiatrist during the Algerian war. The most influential anti-colonial text of the twentieth century. The national bourgeoisie chapter in particular has aged sharply.
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Omeros
Derek Walcott
caribbean
№ 09Omeros
Derek Walcott
The Saint Lucian Nobel laureate’s epic poem. Homer retold along the coast of the Eastern Caribbean. Difficult and worth it.
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The Middle Passage
V. S. Naipaul
caribbean
№ 10The Middle Passage
V. S. Naipaul
Naipaul’s travel account of the West Indies in 1960. Sharp, uncomfortable, often unfair. Worth reading against Kincaid.
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Naked Statistics
Charles Wheelan
data
Start hereNaked Statistics
Charles Wheelan
Statistics without the notation. Explains what correlation, regression, and inference actually mean, which is more than many analysts in practice can articulate.
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How to Lie with Statistics
Darrell Huff
data
№ 02How to Lie with Statistics
Darrell Huff
A short classic from 1954 that has lost none of its bite. If you deal with charts at all, read it once and you will never look at the Y-axis the same way.
Find it on Amazon →
The Signal and the Noise
Nate Silver
data
№ 03The Signal and the Noise
Nate Silver
On forecasting: why most of it is bad and the few domains where it works. Silver builds on base-rate reasoning without ever making it feel dry.
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Thinking, Fast and Slow
Daniel Kahneman
data
№ 04Thinking, Fast and Slow
Daniel Kahneman
The map of how the mind actually handles probability and risk. Long but foundational. Read it slowly.
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Factfulness
Hans Rosling
data
№ 05Factfulness
Hans Rosling
An antidote to the instinct that everything is getting worse. Rosling uses data to correct the reader’s worldview, gently.
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Weapons of Math Destruction
Cathy O’Neil
data
№ 06Weapons of Math Destruction
Cathy O’Neil
On the algorithmic systems that increasingly sort, score, and discipline people, and why many of them are badly built. Essential for anyone building or buying analytics.
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Storytelling with Data
Cole Nussbaumer Knaflic
data
№ 07Storytelling with Data
Cole Nussbaumer Knaflic
The practical manual on communicating analysis. If you produce charts for decision-makers, it will change what your dashboards look like by next week.
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The Visual Display of Quantitative Information
Edward R. Tufte
data
№ 08The Visual Display of Quantitative Information
Edward R. Tufte
The design classic. The examples are dated in places, the principles are not. Read it at a desk with a pencil.
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Moneyball
Michael Lewis
data
№ 09Moneyball
Michael Lewis
Data analytics in a baseball front office. Not really about baseball. About what changes when an industry finally measures the right thing.
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Superforecasting
Philip E. Tetlock and Dan Gardner
data
№ 10Superforecasting
Philip E. Tetlock and Dan Gardner
Tetlock’s study of which kinds of thinking produce genuinely better forecasts. The habits of mind are transferable well beyond geopolitics.
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Man’s Search for Meaning
Viktor E. Frankl
life
Start hereMan’s Search for Meaning
Viktor E. Frankl
A psychiatrist’s account of surviving the camps, and the therapy he built from it. The central claim, that meaning is chosen, not found, is one of the few ideas that hold up under pressure.
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Atomic Habits
James Clear
life
№ 02Atomic Habits
James Clear
The most practical book on behavioural change I can recommend. Short chapters, concrete tools. Read it with a pen.
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Deep Work
Cal Newport
life
№ 03Deep Work
Cal Newport
A case for focused, distraction-free work and the specific routines that protect it. Defensible advice for anyone whose job involves thinking.
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Essentialism
Greg McKeown
life
№ 04Essentialism
Greg McKeown
A discipline for saying no to the good so that the great can happen. Pairs with Deep Work.
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Mindset
Carol S. Dweck
life
№ 05Mindset
Carol S. Dweck
Dweck’s decades of research on fixed vs growth mindsets. The distinction is overused in boardrooms; her original writing holds up.
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Grit
Angela Duckworth
life
№ 06Grit
Angela Duckworth
On the combination of passion and perseverance that produces durable achievement. Caribbean readers will recognise many of the stories about diaspora strivers.
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The Four Agreements
don Miguel Ruiz
life
№ 07The Four Agreements
don Miguel Ruiz
Four short rules rooted in Toltec wisdom. Slim book; ideas that compound. Not everyone’s register, but worth an hour.
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When Breath Becomes Air
Paul Kalanithi
life
№ 08When Breath Becomes Air
Paul Kalanithi
A neurosurgeon’s memoir, written as he was dying of lung cancer. On what makes a life worth living. Read it when you are feeling hurried.
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Can’t Hurt Me
David Goggins
life
№ 09Can’t Hurt Me
David Goggins
Raw, difficult, unpolished. Goggins on mental toughness from childhood trauma to Navy SEAL training. Not for everyone, useful when you need the volume up.
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The Daily Stoic
Ryan Holiday and Stephen Hanselman
life
№ 10The Daily Stoic
Ryan Holiday and Stephen Hanselman
A 366-day calendar of Stoic passages with short commentary. A low-friction way to keep the philosophy reading list above in active rotation all year.
Find it on Amazon →