On the Road is a book that’s tailor-made for reading in one’s 20s. I am no longer in that group, and had a hard time engaging the plot . . . yet, I found plenty of insights from Kerouac’s master work. I spend a bit of time on this one — more than usual. You’ve been warned. And of course I had to include a list of books featuring epic road trips.

I also finished a book called Mastery, which is somewhat well-known in business-y circles. In it, Robert Greene profiles a number of masters in their field (artists, writers, entrepreneurs, etc.), both historical and modern, and lays out the process for how they arrived at mastery. This book, in contrast to Kerouac, seems tailor-made for one’s 30s (even though the process of mastery often starts much earlier than that).

Let’s do it.

On the Road by Jack Kerouac (1957, 293 pages)

“The road is life.”

On the Road is the classic, frenetic novel of the Beat Generation. If you’re asking “Who and what was the Beat Generation?” don’t worry, I asked that as well before I started reading Kerouac. In short, they were a group of young writers and artists in the 1950s who were rebelling against the stiff-lipped society that emerged after World War II. (To be fair, the veterans that came back from WWII were perhaps stiff-lipped for a reason; they had seen greater atrocities than any young artist could fathom. I digress . . . )

This Beat Generation produced cultural works that pushed back against standard norms and carry a frenzied energy that, in book form, can be exhausting to even read — at least as a thirty-something.

On the Road follows a large cast of characters, but it’s mostly about Sal Paradise and Dean Moriarty’s numerous cross-country roadtrips, year after year just continually taking to the blacktop and barreling from New York to San Francisco and back again, finding Des Moines and Denver (two places that I’ve lived) and various other locales in between.

Understandably, it’s a work that’s associated with youthful energy — the freedom, adventure, and limitless feeling of one’s twenties.

So when I picked it up for the first time here at age 31, I was fully expecting to not be able to relate to it. And indeed that was the case. The story went . . . nowhere. And perhaps that’s at least one of the points that Kerouac is making: a life spent in literal constant motion ends up with no plot at all.

While I didn’t much care for the story itself, I did find the writing to be brilliant at times. His descriptions of the various cities and landscapes were sometimes breathtaking and always spot-on. And ultimately, I came away from the novel thinking about the idea of motion. While I’m working on a longer essay about this book, the gist is twofold:

1) Slow Down

“Sal, we gotta go and never stop going till we get there.” —Dean

It’s very tempting to think that constant movement — going from one vacation to the next, from one happy hour to the next, from one freelance gig to the next — leads to greater happiness, fulfillment, satisfaction, and even success. But as Kerouac so brilliantly showed, when we’re in perpetual motion, we’re usually running from something we don’t want to confront. There are various ways we all need to slow down. The holidays are a great time for some practice.

2) Don’t Slow Down Too Much

“But they need to worry and betray time with urgencies false and otherwise, purely anxious and whiny, their souls really won’t be at peace unless they can latch on to an established and proven worry . . . which is, you see, unhappiness, and all the time it all flies by them and they know it and that too worries them no end.” —also Dean

I get that the above isn’t the easiest quote to read (welcome to Kerouac!), but it speaks a lot of truth to middle class, suburban mentalities. I live in a cul-de-sac on the northwest side of the Denver metro area, and it’d be very easy to slow down too much and never give in to adventurous impulse. But sometimes that’s exactly what’s needed. It’s easy to think that kids and lack of time are holding you back, but they aren’t doing so nearly as much as you think they are.

Don’t always tamp down your impulses to take off for a weekend road trip or to take steps to accomplish something you’ve long been dreaming about.

Enough about Kerouac for now . . . moving on!

A Road Trip Reading List

An unconventional list, as most of these aren’t road trip via car, but they’re all very fun.

Don’t Make Me Pull Over by Richard Ratay. A fun romp through the cultural history of American road trips.

To Shake the Sleeping Self by Jedidiah Jenkins. An epic bike trip from America to Patagonia. I had few complaints, but nothing too serious.

Zen and the Art of Motorcycle Maintenance by Robert Pirsig. The classic, sometimes indecipherable philosophical account of a cross-country motorcycle ride.

A Million Miles in a Thousand Years by Donald Miller. A cross-country bike trip undertaken after Miller wrote a bestselling memoir and felt a bit despondent. Really enjoyable book.

Undaunted Courage by Stephen Ambrose. Lewis and Clark embarked on the original cross-country trip, this one by foot and canoe. Great book by the late Stephen Ambrose.

The Oregon Trail by Rinker Buck. This guy re-created a 2,000-mile Oregon Trail journey with a wagon and team of oxen. It’s a very fun read.

Mastery by Robert Greene (2012, 316 pages)

“Our levels of desire, patience, persistence, and confidence end up playing a much larger role in success than sheer reasoning powers. Feeling motivated and energized, we can overcome almost anything. Feeling bored and restless, our minds shut off and we become increasingly passive.”

I’ve been at the same job for nearly seven years, which is an eternity for a Millennial. Rather than feeling an itch for something new, though, my career itch really has to do with mastery. And it’s a feeling that I think a lot of people get in their early 30s . . . you’ve been working long enough to generally know what you like and don’t like, and can therefore lean in to the positives and become a real expert in whatever your field might be.

That’s what this book tackles — the how of mastery.

Let’s start right away with some criticism: Robert Greene is known for his signature writing style of giving the reader tons of historical anecdotes/profiles and then pulling out lessons from them that match his thesis. It’s a style that’s now oft repeated. And while it’s effective, it can also get tiresome. He gives specific stories a universal quality that they just don’t always have. And there were some parts of the book that got a little bit . . . out there and almost weirdly mystic.

That said, I very much enjoyed a lot of this book. The first third or so, about finding your “inclination” (much akin to a calling) and then diving into the “apprenticeship phase” (going headfirst into that inclination) was especially compelling and unlike a lot of what you see in books that are about boosting your career. Lots of underlining in those first few sections. Beyond that, I wasn’t as convinced of Greene’s arguments, but it was still a really well done book.

Anyone in search of mastery — of any skill, hobby, career field — would do well to give this a read.

That’s all for me this week. Hope you all had a great holiday and got some good reading done! Thank you, as always, for the time and inbox space.

-Jeremy

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