A Critical Look at My 2025 Reading List
I asked Claude to analyze my 2025 reading list—not to summarize what I read, but to identify patterns, blind spots, and uncomfortable truths about what my choices reveal. Here's what it found.
The List
In 2025, I finished 27 books. The breakdown:
Business/Leadership/Sales (15 books): Hacking Growth, Your Next Five Moves, The Exit-Strategy Playbook, Hit Refresh, The Five Dysfunctions of a Team, What You Do Is Who You Are, The Private Equity Playbook, The Leader's Guide, How I Built This, Never Eat Alone, Zero to One, The Qualified Sales Leader, Selling the Cloud, Spin Selling, I Will Teach You to Be Rich
Crime Fiction (8 books, all Michael Connelly): The Overlook, The Black Box, The Crossing, The Drop, The Brass Verdict, Nine Dragons, The Lincoln Lawyer, The Burning Room
Science Fiction (1 book): The Ministry for the Future
Fantasy (1 book): Scourged
Non-fiction (2 books): Arriving Today (supply chain), Empire of AI (tech/AI)
Dominant Themes & Mental Models
The Growth-Exit Axis. My reading orbits a very specific lifecycle: startup → scale → exit. Patrick Bet-David, Adam Coffey (two books on PE and exits), Hacking Growth, Zero to One, The Private Equity Playbook. This isn't just "business reading"—it's reading that treats companies as assets to be built and sold. The mental model is acquisition-oriented entrepreneurship.
Sales as Core Competency. Five books directly on sales (Spin Selling, Selling the Cloud, Qualified Sales Leader, Never Eat Alone, Your Next Five Moves). This suggests I see revenue generation and relationship leverage as central to my professional identity—not engineering, not product, not operations.
Leadership as Framework. Five Dysfunctions, What You Do Is Who You Are, The Leader's Guide, Hit Refresh. Leadership here is presented as a set of learnable frameworks—not as something emergent from experience or context. This is very Silicon Valley: leadership as engineering problem.
Biases Worth Examining
Gender Imbalance. Of 27 books, Karen Hao appears to be the only female author. That's roughly 4%. This isn't just an optics issue—I'm missing entire registers of how power, leadership, and business are conceptualized.
The Silicon Valley Canon. My list reads like a YC reading list circa 2015: Thiel, Ben Horowitz, Reid Hoffman's collaborators, Eric Ries, Naval. These authors share a remarkably coherent worldview—meritocratic, libertarian-adjacent, focused on scale. I'm not reading business books; I'm reading a specific ideology of business.
Geographic Monoculture. Nearly 100% American. No European, Asian, African, or Latin American voices on business, technology, or leadership. How do I think about markets, labor, regulation, or organizational culture outside the US context?
The Connelly Escape Hatch. Eight Harry Bosch/Lincoln Lawyer novels. This is telling: my "leisure reading" is procedural, plot-driven, features a competent loner solving problems through persistence. It's comfort food that mirrors the problem-solving identity in my business reading—just with murders instead of metrics.
What This Suggests About My Worldview
I appear to be a mid-to-senior tech/business leader, likely in or adjacent to startups, thinking about exits or transitions. I value:
- Systematized knowledge over tacit wisdom
- Scalable frameworks over contextual judgment
- Optimization and growth as default goods
- Professional relationships as strategic assets
The Ministry for the Future is the notable outlier—climate fiction that grapples with systemic risk and collective action. But it's the exception that proves the rule.
What's Missing
Critical perspectives on tech capitalism. No Shoshana Zuboff, Cathy O'Neil, Meredith Whittaker, Timnit Gebru. Karen Hao's Empire of AI is the closest I got to critical tech journalism, but it's focused on OpenAI's internal drama rather than structural critique.
History, philosophy, social science. No economics beyond business strategy. No sociology explaining why organizations behave as they do. No history that isn't instrumentalized for business lessons.
Literary fiction. Kim Stanley Robinson aside, no fiction that asks me to inhabit unfamiliar consciousness. Crime procedurals let me watch a competent person solve problems; literary fiction forces me to become someone whose problems I can't solve.
Non-Western business thinking. No Confucian management philosophy, no Japanese manufacturing culture beyond what's filtered through American Lean, no perspectives from emerging markets.
Structural critique. I'm reading how to win the game, not whether the game should exist.
The Comfort Question
My list is remarkably coherent. That's the problem. Every book reinforces a worldview where:
- Success is achievable through the right frameworks
- Leadership is a skill to be optimized
- Growth and exit are natural goals
- Problems are solvable by competent individuals
The Ministry for the Future is my one genuine challenge—a book that questions whether individual action and market mechanisms can address civilizational-scale problems. But one book out of 27 isn't intellectual diversity; it's a token.
What Would Actual Challenge Look Like?
- Read someone who thinks venture-backed startups are net negative for society
- Read fiction where the protagonist fails despite competence
- Read history written by the colonized, not the colonizers
- Read business thinking from traditions that don't share American assumptions about individualism and growth
The uncomfortable truth: my reading list is a mirror, not a window. It reflects and reinforces who I already am. A reading diet this coherent isn't expanding my thinking—it's calcifying it.
Recommended Reading to Address These Gaps
Based on the blind spots identified above, here are books that might actually challenge my worldview:
Critical perspectives on tech capitalism:
- Winners Take All by Anand Giridharadas — argues that elite "do-gooding" is a charade that protects the status quo
- The Age of Surveillance Capitalism by Shoshana Zuboff — the definitive critique of data extraction as business model
- Weapons of Math Destruction by Cathy O'Neil — how algorithms encode and amplify inequality
- Chokepoint Capitalism by Cory Doctorow & Rebecca Giblin — how Big Tech and Big Content captured creative labor markets
Fiction where competence isn't enough:
- The Remains of the Day by Kazuo Ishiguro — a man who optimized for the wrong metrics his entire life
- Stoner by John Williams — a quiet life of principled failure
- Revolutionary Road by Richard Yates — the American Dream as trap
- A Little Life by Hanya Yanagihara — success cannot outrun trauma
History from non-Western perspectives:
- An Indigenous Peoples' History of the United States by Roxanne Dunbar-Ortiz — American history from those it was done to
- The Wretched of the Earth by Frantz Fanon — colonialism's psychological violence
- Orientalism by Edward Said — how the West constructed "the East"
- How Europe Underdeveloped Africa by Walter Rodney — development as extraction
Non-American economic and business thinking:
- Doughnut Economics by Kate Raworth — economics beyond growth
- Small Is Beautiful by E.F. Schumacher — economics as if people mattered
- Poor Economics by Abhijit Banerjee & Esther Duflo — development economics that listens
- Debt: The First 5,000 Years by David Graeber — money and morality from an anthropologist
Analysis generated with Claude. The CSV data came from The StoryGraph.