NB: This was a post from back in the day. 2013, I believe. My views have changed since then.

Who says you can’t polish a turd?

“106 gloss units for ostrich!” - Adam Savage

Adam, that is a very shiny poop indeed, except it’s still poop. In many ways, On The Road is a particularly long busting of the shiny turd myth. Beneath the surface, Dean Moriarty is broke; thrice married, twice divorced; a dad who pretends his kids don’t exist; and a deadbeat, manic sunuvabitch. Sal Paradise sees Dean in the beginning for who he is–a turd–knows he’s being conned, but doesn’t care, because he wants to be conned.

He wants to believe in something bigger than life, so he goes along with Dean on the road, witnessing and defending Dean’s selfish, careless behavior. Everything is screaming at Sal that “DEAN WILL ABANDON YOU, TOO,” but of course, what Sal has with Dean is special, no way that could happen to me.

Spoiler alert: Sal gets dysentery in Mexico, and Dean abandons Sal in the middle of another country and takes the car. Damn.

The Catcher In The Road I picked up On The Road primed with the notion that it was a celebration of youth, but instead, got slapped in the face with depressing reality.

Throughout On The Road, Dean and Sal try to find IT, without success. IT is just like the “catcher in the rye.” IT doesn’t exist; IT is part of a fantasy land you created for yourself because you misheard the lyrics; the poem actually is “comin’ thru the rye,” and even after you’re told the correct version, you still want to believe that you’re the guy whose job is to stand on a cliff, catching kids before they fall off, and you make IT your reality. You know the truth, but ignore it, because you want to be conned, you want to believe in IT, you want to be the catcher in the rye.

You want to be conned.

Two lanes Reading On the Road, you can choose one of two lanes.

In one direction, it is the Bible of the restless, the misfits, the young, the beatniks, the people who want to chase the romance of finding IT and in the process, find themselves.

In the other direction, it’s a testament to the power of narcissism and how well we can bend the image of reality to fit us. However, reality exists independently of us, and no matter how often you go On The Road, IT will catch up with you. They never found IT; IT found them.

Which version do you like: the “heroic” one, or the “tragic” one?

There’s no exit Why does this book matter?

One Startup’s Struggle to Survive the Silicon Valley Gold Rush: This is one of my all-time favorite articles.

The prevailing attitude of young, aspiring entrepreneurs, who I identify with, seems to run like this: - Starting a company is cool. - I want to change the world. - I want to discover my calling. - I want to be rich. - I don’t want to be a cog in the corporate machine. - I don’t take orders well. - I want to be the next Steve Jobs. - I want to be important.

All of this sounds great, but the problem is we’re all focused on ourselves; we’re all obsessed with “I, I, I”. After attending the Under 20 Summit recently, I realized that for many of us, it is not so much about changing the world as it is about being the one to do it. Ego blinds us with dazzling flashes of glory and success. Who’s really winning here? Are we really working for ourselves, or for a larger machine? Could we be, in fact, not the bosses, but the labor?

Which version do we want to read, and which version is true?

We all want to believe in the heroic tale; there’s nothing wrong with that. The danger arises when you know the real story but choose to believe the fantasy.

Today’s smart, ambitious youth have replaced Mileys with Zuckerbergs. We want IT, and they have IT, so we want to be like them; we hang around people similar to us, develop an inculture, add this and that to our identities. But when we want something so badly, it’s much too easy to be conned–that is, to con ourselves. VentureBeat and TechCrunch flash their headlines at us: $19 Billion for Whatsapp. $1 million, $10 million, $100 million rounds. Distracting high beams. Dizzying amounts of money. We all want to chase it, but be careful, don’t fall off the cliff, who’s going to catch you?

I am not disparaging all startups, nor am I accusing the system of a sinister conspiracy. Startups are incredible instruments of change. But within the community of young, aspiring entrepreneurs, it seems like we all want to be On The Road for the wrong reasons. We chase the gleam, the shine, the glory–IT–but the ball of shit–hard work, long hours, bad luck, and disappointment–is chasing us. Everything is great until we get dysentery and become feverish; only then does Dean abandon you.

We’re young and we feel like we’re invincible. The lights are ahead, and the heady rush of zeros, commas, and dollar signs honk and capture our attention. There’s one lane of promises and dreams ahead, and quite a lot of ragged-looking people going the other way. Going On The Road is not about going on the road. It’s about ego, delusions, and shiny turds, both yours and mine.

Who’s going to catch you?

I was surprised, as always, by how easy the act of leaving was, and how good it felt. The world was suddenly rich with possibility.

On The Road, by Jack Kerouac

Read it. IT’s a good book.