Navigate to the “three ports” of ancient philosophy to find the good life

Adapted from Beyond Stoicism: A Guide to the Good Life with Stoics, Skeptics, Epicureans, and Other Ancient Philosophers (Jan. 7, 2025, The Experiment).

What is a good life? And how can we chart a course towards it in our chaotic world?

Many of us long for some kind of guide to help us direct our efforts and navigate our existence. And while the details of our modern challenges may differ from those faced by people in the past, fundamental human fears, needs, and desires have not changed. We still want the same things (love, friendship, money, reputation, tranquility) and are still afraid of the same threats (hatred, poverty, sickness, pain, death). 

In light of these timeless human quests, ancient Greco-Roman philosophy continues to offer a useful and inspiring compass for navigating our own lives today, a compass that provides a sense of intentionality in a world filled with uncertainty. Ancient Greek and Roman philosophers have already done a lot of the heavy lifting when it comes to developing a coherent and useful life philosophy. Thinkers ranging from the pre-Socratics to the Neoplatonists spent countless hours considering what is the goal of life—the telos—and figuring out how to move toward it in order to be happy. Their insights can help us navigate even the most treacherous existential waters.

As distant as this ancient period of history may seem to many people, it’s very present to us. That’s because we—the authors of this piece—have put philosophical principles from ancient Greece and Rome to work in our own lives, in particular through our study and practice of Stoicism. Through our own experiences, we have found great value in that era of practical philosophizing and are eager to share these ideas with others. Although we practice Stoicism, we do not believe it is the only philosophy that fits human nature. It is therefore worth exploring how a range of ancient ideas could help us move towards a happier and more fulfilling life. 

Launching a journey to the three ports

In the course of their search for the good life, the Greco-Romans identified three major themes, and their philosophies take us to three corresponding “ports” to explore. 

The three ports are pleasure, including Cyrenaicism and Epicureanism; character, including Aristotelianism, Stoicism, Cynicism, and Platonism; and doubt, including Socraticism, Sophism, Academic Skepticism, and Pyrrhonism. Or, to put it more straightforwardly: feeling good (pleasure), being good (character), and thinking well (doubt). 

These themes encompass much of what people think of when they consider a life well lived. And if you choose to move through these ports on a philosophical journey of discovery, it makes sense to start with the most intuitive (pleasure is good) and work our way to the most surprising (doubt will set you free). 

The far edges of the Greco-Roman philosophical map also hold interesting but mysterious destinations, largely unknown territories that could be labelled (like the edges of legendary ancient maps) “Here Be Dragons.” This region contains the philosophies that offer perhaps less opportunity for modern practice, but which could leave you with some interesting ideas to ponder. The philosophical schools found here are Pythagoreanism, Megarianism, and Neoplatonism. 

Now, let’s take a quick journey through Greco-Roman thought together, briefly traveling to these three ports of call and one more far-flung territory.

The Port of Pleasure

The first port to call on during our voyage is perhaps the most obvious: pleasure. Who doesn’t want to live a pleasurable life? And who, conversely, objects to the avoidance of pain, except perhaps for a small number of masochists? Modern psychological research has accumulated a technical literature on “hedonism,” that is, the pursuit of pleasure. 

Indeed, psychologists have even identified a common problem with such pursuit, what they call the “hedonic treadmill.” This is the idea that we go after a particular pleasure, say, buying the latest shiny smartphone, because it gives us a thrill. The effect of the purchase, however, soon dissipates, and like drug addicts we resume the quest for another shiny object, in search of a repeated hedonic experience. In so doing, we put ourselves on a metaphorical treadmill that leads nowhere and that doesn’t actually make us happy. All it does is line the pockets of our corporate overlords. 

Hedonism, it seems, is a default mode for most human beings. This should not come as a surprise, since pain and pleasure are the two great motivators invented by natural selection to get animals to do what is conducive to their survival and reproduction. Think, for instance, about sex: Would you really go through all the trouble if it were not very—or at least mildly—pleasurable? As for pain, if a gash or a dislocated shoulder were not painful you might not notice before bleeding to death or finding yourself severely impaired when all of a sudden you need your arm to, say, catch a baseball.

Some of the ancient Greco-Roman hedonists were well aware of the pitfalls of “default” hedonism and crafted philosophies of life to circumvent the problems intrinsic in the instinctive, unreflective hedonism by which most people live. This effort produced two schools of thought: the Cyrenaics and the Epicureans.

The two are profoundly different: the Cyrenaics thought that the only thing that matters is immediate physical pleasure, here and now. However, they came up with practices that allow us to own our pleasures instead of our pleasures owning us, thus attempting to bypass the hedonic treadmill. The Epicureans, by contrast, deployed a more sophisticated analysis according to which absence of pain is the real prize since it generates a smooth, calm mental pleasure that is far more desirable than any trifling joy physical pleasure may bring.

The Port of Character

Next in our journey, we can leave the relatively small Port of Pleasure and enter the massive Port of Character, represented by four approaches: Aristotelianism, Stoicism, Cynicism, and Platonism. These are some of the biggest guns in Hellenism, and they offer an interesting variety of perspectives on the very concept of character, why it is relevant, and how to improve it.

In approaching this port, keep in mind that Aristotelianism, Stoicism, and Cynicism form a continuum with respect to one of their crucial tenets: the importance of virtue (which is regarded as a character trait). Aristotle took what is arguably the most commonsensical position: Happiness, in the sense of eudaimonia (that is, a life worth living) requires both virtue (which depends on character) and a number of “externals,” such as health, education, wealth, reputation, and even a bit of good looks. 

The Cynics, by contrast, adopted the most radical stance: Virtue, by itself, is both necessary and sufficient for eudaimonia. Not only that, but externals actually get in the way, and so we should renounce them as much as is feasible. Hence the Cynics’ famous “dog-like” minimalist lifestyle, which included living in the streets and flaunting social norms. 

The Stoics ended up striking a middle ground in this conceptual space: Virtue is both necessary and sufficient for a good life, just as the Cynics said. However, externals have some (indirect, secondary) value, and they are preferred, all else being equal, especially insofar as they make it possible for us to actually exercise virtue and thus improve our character.

The fourth philosophy encountered in this port, Platonism, is a very different kind of animal. In fact, it is so broad and complex that you may wish to limit your exploration. For example, you could focus on Plato’s views on how to build a just society. For Plato, this cannot be done unless we work on justice as an internal virtue: the macrocosm of society reflects the microcosm of the individual. Which means that it all goes back, once again, to character.

There are at least two possible problems with all of these approaches that you should keep in mind. First, there’s the question of what improving your character actually gets you. Pleasure is obviously desirable for most people. But the advantages of a good character are not as plain to see. To paraphrase a familiar New York saying, “Virtue and $2.90 will get you on the subway!” Having a good character doesn’t have the immediate psychological payoff for most people that pleasure does, though it does have social payoffs in terms of your reputation with others. 

Modern philosophers have tried to argue that cultivating virtue is a “reliable bet” for flourishing, but even then they sometimes admit that you can lose that bet. Why should you take a gamble when pleasure bears immediate fruit? (Because it’s the virtuous thing to do, would reply Plato, Aristotle, the Cynics, and the Stoics.)

A second potential issue is that some modern social psychologists argue that “character” is a fiction; the empirical evidence, they say, does not support people having stable character traits, such as being “brave” or “compassionate.” Instead, situations and contexts that people find themselves in are the main drivers of human behavior. If this is true, there’s no way to build character, since there’s no such thing as character in the first place. But the issue is not settled, and defenders of the reality of character seem to be on the upswing.

The Port of Doubt

The final port in the journey through Greco-Roman philosophy is that of doubt, populated by four philosophies: “Socraticism,” Sophism, Academic Skepticism, and Pyrrhonism. Skepticism, which may be used as the umbrella term for these philosophies, has a long history that continues to this day.

In this port, you’ll encounter Socrates, the most famous ancient philosopher, who was a crucial point of reference for many skeptics, as well as for many of the philosophers we encountered earlier. Nevertheless, the Sophists, who either came before Socrates or were his contemporaries, were not “skeptical” in the way he was. In fact, Plato wrote a number of dialogues—including one that takes the title from one of the most famous Sophists, Protagoras—in which Socrates is shown locked in serious intellectual battle with one or another Sophist. 

Two other philosophies, which are most often referred to as varieties of skepticism, co-exist in this port, but they are quite different from each other: Pyrrhonism and Academic Skepticism. 

The Pyrrhonists thought that the goal of life is ataraxia, that is, tranquility of mind. And they were convinced that they had identified the path to it: epoche, or suspension of judgment. The other skeptics, known as “Academic” because they technically belonged to the tradition of Plato’s Academy (and, hence, of Socrates), agreed with many other Hellenistic schools that a good life is one of virtue. But they insisted that human beings can hardly achieve certainty on any subject matter because our senses and ability to reason are both fallible. Therefore, we have to content ourselves with tentative conclusions based on what appears most probable. 

The result, in the cases of both Academic Skepticism and Pyrrhonism, is a very humbling philosophy of life, where people go around admitting that they don’t know anything, or much of anything. It’s fair to say that we could use a bit more of that humility these days. 

Or could we? In good skeptical fashion, we can doubt even that humility and admitting ignorance can lead to a worthwhile life. While pleasure’s payoff is immediate, and character building could bring peace of mind and make the world better off, it’s not entirely clear that being skeptical has enough substance to be a full-fledged philosophy of life. Maybe it’s just a useful attitude to keep in mind. Additionally, even if you desire peace of mind, it’s not evident that skepticism is a better route to achieving that goal than, say, hedonistic Epicureanism or virtue-oriented Stoicism.

As you go forward on this journey, keep these doubts in mind. Perhaps you should be skeptical about skepticism. Or perhaps not! 

Here Be Dragons

The last leg of our journey into Hellenistic philosophy sets off into strange, uncharted waters. Supposedly, ancient maps labeled that sort of territory with hic sunt dracones (here be dragons) to indicate that unknown perils could lurk there. While the philosophies themselves may not be that dangerous, they are still somewhat unusual and little-explored in a modern context. Still, they are historically important and potentially useful today. 

The three schools of thought in this port are Pythagoreanism, Megarianism, and Neoplatonism. 

Pythagoras was incredibly famous in the ancient world, but not for the mathematical theorem you might be thinking of (which was probably discovered by one of his pupils). Stilpo and the Megarians are virtually unknown to us today, yet there was a time in Greece when everyone wanted a piece of Stilpo and regular folks were drawn to “megarize”—that is, to make logical arguments in this school’s style. As for the Neoplatonists, they had the dubious honor of being the last pagan bastion against the tide of Christianity, and one of their members, Hypatia of Alexandria, may have paid the ultimate price for it. 

Both the Pythagoreans and the Neoplatonists leaned toward what we would today call mysticism, though in very different ways and for contrasting philosophical reasons. Ancient people even thought that Pythagoras had a divine nature and went around sporting a golden thigh (believed to be a sign of godliness). And the Neoplatonist Plotinus’s soul was supposedly so great that magic spells meant to hurt him bounced off him and harmed the spell-caster instead. Moreover, his protective spirit was said to be a full-blown god. 

Stilpo, by contrast, was very much grounded in reality and one of the foremost logicians of the ancient world. He managed to influence the most successful Greco-Roman philosophical school of all time: the Stoics. Maybe this isn’t as flashy as having golden limbs or reflecting magic spells, but it still seems pretty impressive!

Since Pythagoreanism was arguably the first philosophy of life articulated by the Greco-Romans and Neoplatonism was the last one, this port spans the entire arc not just of Hellenism but of antiquity as a whole: from the sixth century BCE to the sixth century CE. This is an incredible period of well over a millennium, a time that saw the invention of philosophy and the establishment of a new tradition of writing things down for posterity. Its influence on Christianity and on Western thought more broadly is hard to overestimate. 

Your destination: a personal life philosophy

As befits any philosophical quest, we leave you with an invitation to continue questioning and exploring as you embark on your own philosophical journey.

Our advice: You’re not obliged to pick one school or approach. A thoughtful and personal practice of Greco-Roman philosophy can incorporate a judiciously eclectic range of ideas taken from different schools. In the classical era, a variety of philosophies competed for people’s attention, each one focused on different ultimate goals and a distinctive emphasis on one of our three ports. What is important, in the end, is not the orthodoxy of one set of ideas but the process of seeking a philosophy of life that fits you as an individual. 

Whether you select a specific life philosophy or create your own eclectic path, Greek and Roman philosophies can provide you with an invaluable conceptual map for how to build a life worth living. Let’s use them to make our journey the best it can be.