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Sisyphus with cash-flow problems

When the writing life is like eternally rolling a boulder up a hill

Graham Stewart
3 min readJan 14, 2021
By Franz Stuck Public Domain

I wish I’d thought of the phrase in my headline. It’s Anne Lamott’s description of many a writer’s life. The phrase comes to towards the end of her introduction to Bird by Bird, where she talks about having no regrets for choosing the career she followed.

“I’ve managed to get some work done nearly every day of my adult life, without impressive financial success. Yet I would do it all over again in a hot second, mistakes and doldrums and breakdowns and all. Sometimes I could not tell you exactly why, especially when it feels pointless and pitiful, like Sisyphus with cash-flow problems.” page xxvi

I picked up my copy of Bird by Bird in 1995 in the Kinokuniya bookshop on Orchard Road in Singapore. It was the first book on writing I think I had ever read. I had always been of the “you can’t teach creative writing” school. What I probably meant was I was too pig-headed and arrogant to believe anyone could teach me anything. Understandably, I had written very little by 1995.

Lamott’s voice was warm and encouraging and compassionate. And funny. I’m not sure what the book taught me about the technicalities of writing but it certainly made me feel that doubts and fears and all the things that kept me from the…

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Graham Stewart
Graham Stewart

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