Five philosophy books every entrepreneur should read

Your typical entrepreneurial library—physical or digital—is crowded with books by business luminaries, and full of advice on investment, marketing, hiring, and the like. There is, indisputably, good reason for this: these texts teach concrete, technical strategies that quantifiably boost growth.

The utility of philosophical wisdom, on the other hand, is harder to pin down. Abstract principles of truth, social systems, and human nature are widely considered the domain of ivy-coated universities and academic bookstores, and at first glance, it may seem improbable that Plato or Nietzsche can offer founders valuable guidance.

But what you may not know is that some of today’s most successful entrepreneurs and investors—Peter Thiel, Carl Icahn, and Carly Fiorina—studied philosophy in college. The lessons of history’s intellectual giants have remained applicable to the business world for centuries, and these five works in particular contain theories of startling relevance.

If you’re looking to diversify your bookshelf and expand your horizons, there’s no better place to start than here.

1. Apology by Plato

Socrates was one of the leading thinkers of the ancient world, an iconoclast who was unafraid to question conventional wisdom in his search for truth. Unsurprisingly, this attitude got him in hot water with Athenian elites, who eventually brought him to trial on trumped-up charges of corrupting the young. Apology is an account (written by his pupil Plato) of his defense speech, in which he stresses the importance of skepticism, dismisses the knowledge of so-called “wise men” as fabrication, and proposes instead that the realization of what one does not know is of primary importance. To be innovative, but simultaneously humble and inquisitive, is an attitude consistent with Socrates’s principles, and a key character trait of any successful entrepreneur.

2. Self-Reliance by Ralph Waldo Emerson

The ideas expressed within Self-Reliance resemble those of Plato in the Apology, but with a more explicitly individualist bent. Emerson resolutely believes that conformity is the antithesis of genius—that trust in oneself, rather than in one’s peers or the ancients, is the surest path to success in life. This constitutes an important reminder for founders, who can be barraged with conflicting pieces of advice on a daily basis: follow your instinct, judiciously (but not slavishly) considering the opinions of others and refusing to let authoritative perspectives divert you from the proper course. As Emerson so wonderfully and acerbically puts it, “a foolish consistency is the hobgoblin of little minds, adored by little statesmen and philosophers and divines.”

3. Twilight of the Idols by Friedrich Nietzsche

The subtitle of Twilight of the Idols is How to Philosophize With a Hammer, and that is deadly accurate. Nietzsche eviscerates the traditional notion of an ideal, or “real” world beyond the senses, characterizing it as an unobtainable and hence useless abstraction. Although his anti-moral stance (expressed elsewhere within the work) is definitely not something for entrepreneurs to emulate, his acceptance of the less-than-perfect can be reconstituted as sound business strategy. Starting a company entails give-and-take, lowered expectations, and adaptation to unforeseen circumstances. Almost nothing ever works out exactly as planned, and whether you stumble upon misfortune or make it big in ways you never imagined, it helps to remember Nietzsche’s famous maxim (which, incidentally, also comes from this work): “What does not kill me makes me stronger.”

4. Pragmatism by William James

One of the perks of reading James is that his philosophy is purposely written in terms accessible to the average reader—he eschews philosophical jargon in favor of plain English. That makes this volume, comprised of a series of lectures, all the more appealing and informative. Pragmatism supports the idea that in order for a statement or principle to be designated “true,” it must be verifiable by experience. This same tactic can provide a much-needed check on young entrepreneurs’ flights of fancy—a great idea, James reminds us, is not enough. If it is to prove worthy, it must be grounded in economic and social reality, and must give rise to a sustainable and profitable business model that fills an actual need in the market. Otherwise, it can never materialize.

5. Politics and the English Language by George Orwell

If there has ever been written a more urgent defense of communicational clarity and straightforwardness, I haven’t read it. Orwell—author of the dystopian novels 1984 and Animal Farm—uses this essay to explore the ways in which euphemism and vague phrasing disguise political systems’ flaws, but his overarching message has implications for the private sector as well. Institutional transparency is first and foremost the product of honest, direct communication between a company’s leadership, staff, and customers. This makes it essential that all parties involved have a thorough command of language, a facility with writing, and an understanding that the truth, no matter how difficult, must be told. Politics and the English Language is short—probably the shortest work on this list—but its significance is paramount.

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