I sat down earlier to write a post about a recent experience I had at work. I got midway through what had initially seemed like an interesting anecdote when I realized, This story sucks—I’m riding the rails. I quickly scrapped the original plan and instead decided to write about the phrase, Riding the rails, as I’ve come to use it.

The phrase came into my lexicon several years ago after a failed mountaineering attempt of Mt. Adams, a 12,000′ mountain in southern Washington. After the climb I was sitting with several buddies in Hood River, OR, at a bar on a hill overlooking the Columbia River, drowning our disappointments in beer. On the north side of the river runs a train track, and as we sat there nursing our dejection a freight train chugged past. I looked across the river and said,

“I’ve always wanted to ride the rails. You know, go hobo, hop into a boxcar and just see where I end up.”

The fellas sipped their beers and nodded. We were a group of six guys: this desire was relatable to us all. One member of our group—the member, in fact, whose presence had guaranteed the failure of our summit-attempt, a fact that had earned him neither gratitude or appreciation amongst the rest of us—said, I did that once.

Seats creaked as we all turned and looked at him. This was new. This was interesting. This guy—let’s call him Albert for anonymity’s sake—who up until this point in our 36-hour adventure had been nothing but an albatross, was suddenly revealing a far more intriguing side of his personality.

The Albatross nodded as we continued to look at him. Sunlight glinted off his cool blue eyes. Out the window the river continued to flow calmly past.

“Well what happened?” somebody asked.

Albert the Albatross sipped from his beer and leaned forward in his seat. We leaned to meet him. Excitement stirred our insides where before there had only been grumbling and frustration.

Well, we were in Seattle. A friend and I went down to SoDo where the trains transfer and stop. We waited for a train to come to a halt and then, after making sure no one was watching, we ran and hopped into a boxcar. We hid inside behind the door until the train started moving.

Albert sipped from his beer. Our brains fired universes of excitement imagining the adventures that had next befallen Albert-the-about-to-become-Awesome. Anticipation rose tidally. Eyes twitched. Necks were craned and lips were licked. Somebody nodded for Albert to continue.

Yeah, so the train pulled out and got moving. It went kind of slow at first but then began to pick up speed.

Albert stopped. An astonishing and comprehensive quiet wrapped itself like a wet blanket across the bar. Patrons turned on their stools and the TV’s muted themselves. Upon the windowsills birds perched in anticipation.

“And?” somebody invited.

The train went south to Portland. That’s where it stopped. And then we got off.

A long empty pause. Outside, a leaf fell slowly from a tree and landed upon the grass with a quiet pfff. Finally, someone voiced the thought we were all thinking.


Yeah, we got off in Portland and bought bus tickets back to Seattle. That was it. That was our trip.

Oh Albert. Albert Albert Albert.

The room welled with disappointment, incredulity, head-scratching. About us sound slowly returned to the bar. The bartender lowered his eyes into his bin of ice. The door clanged behind an exodus of smokers. Birds shook their heads and harrumphed their way back to their nests. Ashamed, the fellas turned away and would not meet one another’s eyes. Someone sniffled.

And out of this experience was born my understanding of the phrase, Riding the rails.

The point isn’t simply that this could have been an awesome story—in fact, it should have been an awesome story—that instead turned out to be a pointless bunch of bunk. And it’s also not that Albert, in addition to being a terrible mountaineer, was also a horrible storyteller (such people exist, and they are legion).

No, riding the rails is larger than Albert and refers to something that can befall any of us, even the most gifted storyteller. Riding the rails refers to that moment when you’re midway through a tale—the fist-fight at your brother’s wedding with your drunk uncle, the woman whose skirt ripped completely over her head as she tripped and fell from the bus—and you realize, inside and quietly to yourself, This story ain’t no good. It’s got no teeth. It can’t hold its water. It fails to inspire… Whatever metaphors float your boat, the point is this: your story is sinking, the ending payoff won’t justify the time spent telling it, and you’re wasting listeners’ times.

It’s a terrifying moment, this realization, and it happens because not every story justifies its telling. That is, all storytelling navigates an economy where time-spent-explaining is contrasted against the pleasure-derived-from-the-story, and sometimes the ratios simply don’t work out. What’s worse is that the moment of awareness is a horribly solitary one, for despite the sudden insight that your story sucks your listeners continue looking at you in expectation of something satisfactory, and you alone know that you can’t deliver the goods.

Riding the rails happens, and I believe it happens to even the best storytellers. I see three different ways to address this problem. The first two are opposite ends of a spectrum while the third stands outside or above the others. All three are based upon personality stereotypes I hope you will permit me to employ: the unaware/boring person, the creative person, and the good narrator. We’ll proceed in order.

When confronted with a situation in which they’re riding the rails, the unaware person will simply finish the story. For such a person, We rode the rain to Portland and then got off is a completely satisfying conclusion. It’s factual, it’s simple, it’s clear and direct. Contained deep in the hearts of such people are a certain ignorance and dullness to the fact that communicating with one another is really the most exalted of human actions, and is not something to be undertaken with the dull objectivity of a computer reporting data. Such people are boring and untrustworthy, and should never be elected to positions of power.

On the other hand the creative person—God bless him or her—will resort to what humankind’s been doing since the Garden of Eden: they’ll lie. The moment they realize that their story isn’t any good they’ll start making things up to compensate and grab the listener’s attention. Suddenly the boxcar they were riding in will have been inhabited by a grimy hobo, or maybe three grimy hobos huddled around a fire, or eventually five grimy hobos huddled around a fire sacrificing rodents to Satan… and so on.

The liar’s outcome, while much more fun than the boring person’s factual reportage, is ultimately only slightly less unsatisfying, for while you might laugh and wonder about that crazy story on the train where five hobos were decapitating prairie dogs with medieval falchions, in the end you’ll know that the story’s bullshit. More significantly, you’ll know that your narrator is a bullshitter, and while we all fib to a degree, once you peg someone as a bullshitter you’ll never be fully engaged or moved by their stories again. This doesn’t mean you won’t be entertained by the bullshitter—you will; only you won’t ever invest as much stock into, and thus be moved by, their narrative offerings.

Lastly, there’s the good narrator. I admit that this is a rather boring title, but please don’t jump ship based upon flaccid nomenclature. The good narrator cares deeply about communication between people. She realizes that conversation is an art-form, that life without art-forms is insipid, and that the best way to present her art is neither through a crude recitation of facts nor an exalted series of lies. Instead, when confronted with the realization that her story’s not going to cut it, the good narrator stops her tale, holds up her hands and acknowledges to her audience, Hey guys, sorry, but I’m riding the rails here.

When she does this it is understood that her story—which initially had seemed interesting and worthwhile—no longer meets expectations. She tried, but for whatever reasons it simply isn’t working. Effectively, the good narrator is calling check-mate on herself, and while the listener might properly be disappointed by the incompleteness of her tale, it’s a preferable outcome to boredom or lies. This is a maneuver that should be treated with respect, for it takes courage to be honest and admit failure.

This isn’t the end of the equation. There’s one more step needed to regain social equilibrium after riding the rails has been admitted. The appropriate response when a good narrator admits defeat is to pat her gently on the shoulder, look kindly into her eyes and say, Thanks for being honest, we’ve all been there, don’t worry about it. Because it’s true, we’ve all told stories that seemed great inside our heads but landed like a sack of molding potatoes on our listeners’ ears.

So let’s ‘fess up and face the facts—inevitably we all ride the rails, and more often than we might like to acknowledge our stories are less-than-great. The best thing to do is admit failure, respect the value of a good story told well, and hope that next time you’ll knock their socks off.