On Jack’s Road: Kerouac and the American Road Trip—Interview With Brendan Leonard


“What is that feel­ing when you’re dri­ving away from peo­ple and they recede on the plain till you see their specks dis­pers­ing? — it’s the too-huge world vault­ing us, and it’s good-bye. But we lean for­ward to the next crazy ven­ture beneath the skies.” 

—Jack Ker­ouac On The Road

Forty five years after his death, there are few writ­ers who have had as much influ­ence on Amer­i­can lit­er­ary cul­ture as Jack Ker­ouac. Gen­er­a­tions of nomads, vagabonds, and dirt­bags found them­selves drawn to his works, roman­ti­ciz­ing the open roads of the Amer­i­can West. One of them is Bren­dan Leonard, a writer, climber, and founder of the pop­u­lar blog, semi-rad. A not­ed Ker­ouac fan who once gave a copy of On The Road to woo a date, he set he set off on a jour­ney of his own to search for answers in a try­ing time, which he doc­u­ment­ed in his first book, The New Amer­i­can Road­trip Mix­tape. Today, Bren­dan shares his thoughts on the influ­ence that Ker­ouac has on the mod­ern road-trip, the authen­tic­i­ty of tak­ing the same trip today, and the philoso­phies that Ker­ouac impart­ed on his travels.

THE CLYMB: What was Jack Kerouac’s goal in his travels?
LEONARD: I think his real goal was expe­ri­enc­ing life, and my inter­pre­ta­tion of a lot of his writ­ing is that he want­ed to see and expe­ri­ence as much as he could. Of course he saw a lot of Amer­i­ca in his trips, but it was more about peo­ple, culture—and not just the art we think of when we think of the word “culture”—but the dif­fer­ent cul­tures in Amer­i­ca. The things you learn from spend­ing time with peo­ple you might oth­er­wise nev­er spend time with if you didn’t hap­pen to run into them in the mid­dle of nowhere in Texas, or in a jazz club, or a par­ty you hap­pened to go to because you hap­pened to be in town on the right night.

THE CLYMB: Are road­trip­pers, nomads, and dirt­bags seen as counter-cul­ture in today’s society?
LEONARD: We have this sense nowa­days that we need to be ful­ly employed for our entire lives, which means we’re rel­e­gat­ed to only tak­ing time off when we have paid vaca­tion. I think that’s a mis­take, and it makes us think that we have to spend basi­cal­ly every week of every year mak­ing mon­ey. If it’s a Mon­day, we’re either at work, or we’re tak­ing a paid vaca­tion day (which means we’re still get­ting paid). Most of us nev­er have the fig­u­ra­tive balls to ask a boss for unpaid time off, because we can’t imag­ine that we’d allow our­selves to be “unpro­duc­tive” for a week—or be allowed by our employer.

THE CLYMB: What was Jack Ker­ouac and Neal Cassady’s phi­los­o­phy towards trav­el and the road trip?
LEONARD: Jack Ker­ouac and Neal Cas­sady were com­fort­able let­ting the next whim take them where it may. Did they ever have any mon­ey? Not real­ly. Did they do some things that most of us would nev­er want to do in order to keep their trip going? Def­i­nite­ly. Were they wor­ried about get­ting back to their next job so they could keep work­ing their way up the cor­po­rate lad­der? Def­i­nite­ly not. So they were not on a trip, at least one where they tried to pack every­thing into 10 paid days off. They also both lived very hard and died very young, which of course isn’t some­thing most of us want to emulate—but I think we can learn from their idea of what a road trip was: it was just life, and an “unpro­duc­tive” part of life, but an incred­i­ble part.

THE CLYMB: Why is the road trip, in the spir­it of Ker­ouac and Stein­beck, such a revered part of Amer­i­can culture?
LEONARD: Our roads are per­fect for that type of think­ing you want to do when you set out on a big road trip—interesting, but not so ath­let­ic that you have to devote 100% of your brain­pow­er to stay­ing on the road, like they are in the moun­tains in Europe. In the U.S., we’ve got moun­tain roads, but in between, we have long stretch­es where you can hold onto the steer­ing wheel with one hand and gaze out the win­dow at the scenery and let your thoughts drift a lit­tle. I don’t think you can do that in the nar­row roads and hair­pin turns of the Alps. Plus, the West­ern Unit­ed States has a his­toric rep­u­ta­tion of being a place where you can find, or rein­vent, your­self, and I think the West has some of the best road trip­ping ter­rain in the coun­try. The idea of a road trip is pret­ty roman­tic, not in the love sto­ry sense of the word, but in the On The Road sense of the word.

THE CLYMB: Does Ker­ouac and On The Road reflect a bygone era? Is trav­el in his time more roman­tic and authen­tic than to take the same trip in today’s world?
LEONARD: No one’s going to take that same trip, or write the same book On the Road was when it came out (and still is). It was a rev­e­la­tion to many peo­ple, and you obvi­ous­ly can’t have that same rev­e­la­tion now. Our trips are also rel­a­tive­ly less adventurous—there are few spots in the Unit­ed States where you can dri­ve more than 100 miles with­out going by a gas sta­tion, and we have cell phones for emer­gen­cies, and AAA. Can you still take an authen­tic and roman­tic trip today? Of course, authen­tic­i­ty to me is hon­esty, and if you’re hon­est about what you’re expe­ri­enc­ing, your trip is authen­tic. And romance is all about being open to expe­ri­ence, and in the moment. A lot of that gets sucked out the win­dow because we’re not present when things are hap­pen­ing, and we’re not open to them. I’ve had roman­tic moments where I’m dri­ving down the PCH, a great song play­ing on my van stereo, and the sun set­ting over the Pacif­ic, and I know it’s a great mem­o­ry hap­pen­ing right now. But then I’ve had that same moment on that same stretch of road and I’m think­ing about work, or check­ing my social media feeds on my phone, and I’ve total­ly missed the moment because I’m just not there.

THE CLYMB: Has con­stant com­mu­ni­ca­tion through social media changed the mod­ern road trip?
LEONARD: If you’re open to it and are present, a road trip can be a beau­ti­ful, amaz­ing thing. If you’re con­stant­ly wor­ried about how you’re going to com­mu­ni­cate all the dai­ly hap­pen­ings of your trip on Twit­ter and Insta­gram, well, you’re prob­a­bly going to have a much dif­fer­ent experience.

THE CLYMB: Read­ing and being inspired by On The Road, how did it affect your journeys?
LEONARD: I think Thomas McGuane put it best in an essay I quot­ed in my book, The New Amer­i­can Road Trip Mix­tape: “He trained us in the epic idea that…you didn’t nec­es­sar­i­ly have to take it in Dip­stick, Ohio, for­ev­er. …Ker­ouac set me out there with my own key to the high­way.” I think it impressed upon me, when I was a teenag­er read­ing it for the first time, the roman­tic notion of find­ing answers out on the road.