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September 2019  marks the twentieth anniversary of Jay’s decision to become a writer. His gift to you all this celebratory year is DO IT – Twelve hard lessons on learning by failing, succeeding by accident, never giving up and saying FXXK WRITING all at the same time. You’re welcome!

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Analogies are illustrative but not always helpful, especially in a writing career. The world of publishing is so strange, counter-intuitive, and always unfair. The world of art is often mysterious and personal and yet of a time and place that makes connections with others. Smack these two elements together and analogies abound even if they never really do anything constructive. So, here are some of the best analogies that I’ve been able to muster to explain craft and career. Like my bizarre career, they are idiosyncratic as shit, but they may help you make your own.


Each short story is a hobo. They ride the rail, looking for a place to plant themselves and make some dough from labor and guts. Often, no one will pay for their efforts, so they grab their bindle (your manuscript), avoid the bruising of the Railroad Detective (harsh rejection letters), then hitch a ride to the next town and try again (submissions)


 Chares Wilford called them a case study of the writer’s heart and mind. I’d contest that and say they are more likely biographies of your imagination. Taken together they are the library of your hidden and visible desires and fears. 


Consider the world of publishing a casino. The fanciest ones are in New York, and there are dozens of smaller ones and more crooked ones scattered around the locales where desperate writers gather. The writer comes in with a handful of chips (novels, collections, poetry). They belly up to the blackjack table, gaming the dealer and the other writers out for a big payday by counting cards, hoping to double their luck with what they have. Or they sit at the poker table, hoping they can outfox the other players with names like Trending, Bestseller, and Oprah’s Pick. Sometimes the writer’s whole life is in those chips. Sometimes nothing more than twenty. Sometimes the odds are in their favor. Others its snake eyes no matter how many dice rolls. And sometimes there are jackpots that can’t be repeated. Play it well, you’ll walk out with more than you came in with. Play it desperate and you’ll be thrown out kicking and screaming about how you were one card away from the Shangri La payday.


A semiotics class that you’re failing. 

© Jason S. Ridler

Meet the Author

Jason S. Ridler, professional author and historian

Jason S. Ridler

Jason S. Ridler is a writer, historian, and actor. He is the author of The Brimstone Files, and his latest historical work Mavericks of War was called a “visceral read that is also an important piece of scholarship” by Pulitzer-Prize winner Richard Rhodes. He is a Teaching Fellow at Johns Hopkins University and teaches creative writing at Google, Youtube, and for private clients.

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