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How I Make Money Writing

How a Bestselling Author Built a $150K Freelance Gig Portfolio

The prestige of publishing bestselling books rarely equates to financial stability. For Steve Almond, a celebrated author, former podcast host, and writing teacher, surviving in the modern media landscape means operating as a glorified gig worker. After 35 years of writing professionally as a writer and teacher, his earnings range has fluctuated wildly, yielding absolutely nothing during his early years of writing poems and short stories before eventually topping out at $150,000 during his most lucrative year.

Despite writing successful books like Candyfreak and co-hosting the hit Dear Sugars podcast, Steve’s book royalties constitute a fraction of his actual income. To support a family of five in an expensive part of the country, he relies on a chaotic patchwork of independent revenue streams. His yearly income is assembled from dozens of 1099 tax forms generated through freelance assignments, manuscript consulting, speaking gigs, and online classes. 

Operating without an employer safety net means he must also shoulder the heavy burden of out-of-pocket health insurance. This stark economic reality informs his most pragmatic advice for independent creatives. “To the extent you can, uncouple your artistic creation from your financial expectation,” Steve warns.

Because he lacks a predictable salary, evaluating freelance opportunities requires a strict financial filter. He cannot afford to take on demanding editorial work for low pay without it impacting his household. When deciding which teaching or consulting gigs to accept, he calculates what he calls the resentment threshold. “I have to make sure the pay is worth the time and energy invested,” Steve explains. “Am I getting paid enough for this that I’m not going to resent the work, when it starts to slog?”

Managing this relentless hustle while parenting three children creates a constantly unpredictable daily schedule, leaving almost no room for the deep focus required to write fiction. For thirty years, his pattern was to write a failed novel, get depressed, and then write a non-fiction book to recover financially and emotionally. 

To break this cycle and finally finish his celebrated novel All the Secrets of the World, he had to completely abandon the idea of writing at home. Steve and his wife engineered a radical, logistical escape from their domestic swirl to get deep work done, but structuring that kind of recurring physical separation requires a highly specific operational strategy.

To learn about the mindset shift Steve used to finally publish a successful novel after 30 years of failed attempts, subscribe and read the full interview on How I Make Money Writing.

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