4 Classic Books That Offer Contemporary Wisdom


One thing millennials are not in short supply of is advice. Older generations seem to have suggestions and criticism in spades, even if their guidance is often conflicting, and at times out of sync with the fast-paced world we live in.

Some things, however, have not changed. In contrast to recent books like Are You Smart Enough To Work at Google and 50 Shades of Grey, classic literature holds some quiet, timeless wisdom that our generation sorely needs. Here are four classic books you should read in your 20s, and why.

1. Jack Kerouac's 'On The Road ': On the Pursuit of Passion

“I realized these were all the snapshots which our children would look at someday with wonder, thinking their parents had lived smooth, well-ordered lives and got up in the morning to walk proudly on the sidewalks of life, never dreaming the raggedy madness and riot of our actual lives, our actual night, the hell of it, the senseless emptiness.”

Reading On The Road in your 20s is a revelation in a way that it isn’t in your adolescence. Even Kerouac, in all his glorious insanity and firmly in the grips of feverish youth, has to deal with pesky reality: budget constraints, missed connections, and that familiar, all-consuming sense of incomprehension. Though it was written decades ago, many of the book's lines still hit where it hurts. His idyllic, winding trip is full of eye-openers, but with all its detours, stops, and descriptions, it's also repetitive and exhausting. Where, a few years back, On The Road may have made you want to jump in the first car you found and set off on a grand adventure, in your 20s it can remind you of the slow, agonizing morning after the night you felt completely alive, or the eleventh hour of a long-distance adventure, when you're bloated and tired and craving stability. Kerouac’s novel is a good reminder of the necessity of passion in our lives, and the limits of living exclusively for it.

2. J.R.R. Tolkien's 'The Lord of the Rings': Fairy Tales for Grown-Ups

“It's a dangerous business, Frodo, going out your door. You step onto the road, and if you don't keep your feet, there's no knowing where you might be swept off to.”

Most, if not all, members of our generation have had a crash course on the trilogy, thanks to the work of director Peter Jackson, and an award-winning cast that was very easy on the eyes (can anyone say ‘Aragorn’?). But Tolkien’s books are far richer in imagery, imagination, and feeling than Jackson’s film adaptations. Our confusing journeys through this decade of our lives can sometimes feel akin to a hobbit’s trek to Mount Doom. With kindness, humour, wisdom, and no shortage of elves, Tolkien offers us an underdog story wrapped in a fairy tale, for the moments in which we may need to believe in one.

3. Fyodor Dostoyevsky's 'The Brothers Karamazov': Philosophy for Beginners

“The world says: 'You have needs — satisfy them. You have as much right as the rich and the mighty. Don't hesitate to satisfy your needs; indeed, expand your needs and demand more.' This is the worldly doctrine of today. And they believe that this is freedom. The result for the rich is isolation and suicide, for the poor, envy and murder.”

Crime and Punishment is the book most often associated with Dostoyevsky, but The Brothers Karamazov is far greater in scope (it's also far longer and harder to get through.) Dostoyevsky’s desolate Russia is a far cry from our own overcrowded cities, and his landless peasants may seem alien to our overly connected and often overprivileged selves. Yet they struggle with some of the same things we do: what makes a good life, what makes a good person, what success is, and how to find happiness. (The book also delves a fair bit into religion, suffering, and free will, in case the rest was not quite enough to fill your Sunday afternoon.)

4. J.D. Salinger's 'The Catcher in the Rye': On Growing Up

“That's the thing about girls. Every time they do something pretty, even if they're not much to look at, or even if they're sort of stupid, you fall in love with them, and then you never know where the hell you are. Girls. Jesus Christ. They can drive you crazy. They really can.”

Holden Caulfield was everybody’s inner monologue in high school. Read later in life, Holden can not only serve as a reminder of our younger selves, but give us a dose of unadulterated empathy and naivety in an adult world that does not allow for much of either. Though The Catcher in the Rye’s sentimentality is unsustainable — even Holden admits as much — in a world of unfulfilling jobs, uncertain futures, and friendships and romantic relationships that change faster than we can update our statuses, there is something wonderfully comforting about the escapism of sitting with Holden and watching Phoebe Caulfield ride a carousel.