“Life is hard,” the actress Katherine Hepburn once quipped, adding, “after all, it kills you.” Given the unavoidable end to the enterprise, then, it’s a good thing we can draw courage from the intelligence of the ages.

We’ve long been interested in the hard-won wisdom of our elders. Earlier this year, in fact, we put together a list of life advice from luminaries, which contained a great read called Breakfast with Socrates. Now its author, Robert Rowland Smith, has returned with a sequel of sorts. Bearing its own catchy title, Driving with Plato: The Meaning of Life’s Milestones, Smith’s latest provides an equally entertaining and insightful consideration of what the greats might have to say about such passages of life as going to school.

Where Breakfast with Socrates took as its structural unit a typical (Western) day, Driving with Plato considers the benchmarks of an entire life — both biological and culturally constructed — from birth onward. One chapter, for example, examines the challenge of first learning to ride a bike:

You have to embrace what in Kierkegaardian philosophy is the madness of decision, the vertiginous split second when reason must, in the name of action, go into suspense. In this critical instant of changeover, success arises only if you go at a considerable speed, if you seize the challenge of creating your own forward momentum… As Einstein (whom we’ll come to later) put it, when comparing riding a bicycle with life, “To keep your balance you have to keep moving!”

A cynic might say that Smith and his publishers were looking to exploit a clever conceit, but the book’s research and writing belie this charge. In fact, it’s altogether to the author’s credit that he creates a coherent narrative out of such disparate cultural, literary, and philosophical material.

Driving with Plato selects an appealingly wide range of sources, from Noam Chomsky to Curb Your Enthusiasm, and Smith’s prose smoothly carries the reader over the road he’s delineated. On the bain of human experience — moving — he offers this:

Probably the worst accidents at home must be those involving fire, but they’re not always such a bad thing. Rumi, the great thirteenth-century Sufi mystic, has a poem in which his house burning down makes him grateful. Why? It affords a better view of the rising moon.”

From losing one’s virginity to the ultimate loss of life itself, Driving with Plato is delightful proof of how wisdom provides ballast amidst the chaos we all have no choice but to confront.

Kirstin Butler is writing an adaptation of Gogol for the Google era called Dead SULs, but when not working spends far, far too much time on Twitter. She currently lives in Cambridge, MA.