Gateway to Philosophy: 5 Great Books to Get Reading

Mark Twain once said,  “A classic is something that everybody wants to have read and nobody wants to read.” Glancing through book lists like the Great Books of the Western World or The Harvard Classics, it’s hard to argue with Twain’s sentiment. The great books often appear daunting, especially for novice or younger readers. Many of the books are long, containing hundreds of pages or several volumes. Even experienced readers can be turned off from difficult topics like philosophy or theology. Therefore, it is helpful to highlight some of the “easier” classics that may lead one to read other treasured literature. Here, we will look at five works of philosophy that are short, straightforward reads that still illuminate the reader in the way one expects of a classic. 

The Apology by Plato

The Death of Socrates by Jacques-Louis David (1787) [1]. In Plato’s Apology, Socrates defends himself from his accusers. After conviction, he is sentenced to death and dies by drinking hemlock.

The Apology, written by Plato, details Socrates’ defense at his trial shortly before his execution in 399 BC. Socrates defends himself from the charges of corrupting the youth and teaching falsehoods about the state gods brought upon by three prominent Athenians. The work is a prime example of the Socratic dialogue in which Socrates displays a masterful knowledge of interrogation techniques toward one of his accusers, Meletus. At roughly 25 pages long depending on the edition, The Apology is easily digestible. Because Socrates himself left no writings, the work is essential in understanding the life and teachings of the “Father of Philosophy”.

We recently released a podcast breaking down The Apology in detail. Check it out here.

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Crito by Plato

Crito, fourth from left, closes the eyes of his deceased friend Socrates in a late 18th-century bas-relief piece by Italian sculptor Antonio Canova [2]. In Plato’s Crito, Socrates and his friend discuss the recent trial before the philosopher’s death in 399 BC.

Crito, another work by Plato which details an episode of Socrates’s life, can be approached as a sequel to The Apology. This brief dialogue is presented as a conversation between Socrates and a friend named Crito where Socrates recounts his arguments during the trial. Additionally, the work explains Socrates’ reasoning for accepting his death sentence rather than fleeing the city, exploring the relationship of an individual to the state. Like The Apology, Crito is a must read for anyone wishing to learn more about the great Greek philosophers.

Check out Crito’s recent breakdown here.

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Meditations by Marcus Aurelius

Bust of Marcus Aurelius, the author of Meditations [3].

Never intended for the public, Meditations is a collection of personal insights and observations that Roman Emperor Marcus Aurelius recorded while on military campaign. This thought-provoking diary is still read widely after nearly two millennia, provoking contemplation in audiences of all backgrounds. Meditations is often considered the epitome of stoic philosophy, although Aurelius draws on multiple schools of philosophical thought. The work is a unique opportunity to peer into the unfiltered thought of a man remarkably positioned as the leader of the greatest empire in history. Great for daily reading and inspiration, Meditations offers the modern reader a wealth of practical wisdom from someone who reached the pinnacle of success.

If you’d like a breakdown of the topics covered in Meditations, check out our recent article here.

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The Prince by Niccolo Machiavelli

Title page from “Il Principe” (The Prince) by Niccolo Machiavelli [4].

An oft quoted work, The Prince by Niccolò Machiavelli is a 16th century guidebook instructing rulers on effective governance. It is considered one of the first works of political philosophy and popularized the term “Machiavellian” to describe politically cunning or scheming behavior. This is a good read for anyone who wishes to understand the motivations and reasoning behind great leaders from the past or savvy politicians today. At approximately 130 (short) pages, The Prince is a quick read, however the reader may want to take their time in order to fully digest the concepts Machiavelli brings to light. 

Want to apply Machiavellian principles to your own life? Check out our recent article here.

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Man’s Search for Meaning by Viktor Frankl

Viktor Frankl, author of Man’s Search for Meaning [5].

Though perhaps more psychology than philosophy, Viktor Frankl’s Man’s Search for Meaning reflects upon man’s resilience in the face of adversity and offers the reader a glimpse of how an individual’s philosophy can determine their outcome. Analyzing how prisoners (including himself) in Nazi concentration camps dealt with their bleak circumstances, Frankl develops his theory of logotherapy, proposing that man’s primary motivational force is to find meaning in life. At the time of Frankl’s death at the end of the 20th century, the book boasted sales of 10 million copies and was considered one of the most influential books in the United States. Less than 200 pages, Man’s Search for Meaning pushes the reader to ponder the extremes of life, packing a punch that few other works can deliver.

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More to Explore

For those who don’t know where to begin reading the great books, this concise list should serve as a launching point into heavier and more consuming works. Each of the works above can be finished quickly, but the content is best absorbed when approached methodically, allowing the reader to truly converse with the text. One should approach any work with patience and a willingness to “wrestle” with the content. In this way, the reader’s mind will be strengthened by the experience and will better read, comprehend, and digest other works.

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Image Sources


[2] Image provided by Fondazione Cariplo, Creative Commons License:,_Critone_chiude_gli_occhi_a_Socrate.jpg


[4], Creative Commons License:


[6] Title Photo:

3 thoughts on “Gateway to Philosophy: 5 Great Books to Get Reading

  1. It is not possible to post a list of any sort without some curmudgeon chiming in to say, “But what about ___?” So here I am. I would have included Lewis’s The Abolition of Man. At ~80 pages (just over 100 with notes) it’s very readable.

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