Writing Toward Uncertainty

Why the Best Work Comes from Doubt, Not Perfection, with a nod to Lucy Sante

As I move into my twilight years, I don’t feel a sense of ease or flow, but rather a need to do better. Almost all writers or artists have that one theme to which they return repeatedly. Readers of such authors often find comfort in knowing they can rely on the writer to entertain or inform in a familiar manner. While some readers appreciate a writer’s recurring themes, I’ve come to believe that revisiting those themes is not about echoing the past, but rather about deepening it.

I consistently return to the source of my work, and my first instinct is to rewrite or even remix what I have written before. However, for me, it's never fulfilling if I’m merely going through the motions of writing, resulting in just more output at the end of the day. To keep a blog audience, writers often stick to a familiar format they believe readers expect, fearing they might stray from it. From my perspective, that is a form of failure. Many writers I admire have often succumbed to a formulaic approach, trying to please their readers to gain likes or out of fear of losing their audience. This is a fear that I believe every blog or Substack writer faces regularly.

Breaking through the barriers developed from one’s practice and embracing doubt and fear can create an exhilarating interplay. When I write something for Substack and feel nervous right before posting, I recognize it carries potential. Perfection is not my goal; I prefer my prose to retain a rough edge, allowing readers to interpret the material in their own way. What makes blog writing distinct, I believe, is the structure of the platform itself—it invites a conversation, a tension, between writer and reader.

On one level, it’s prudent to regard your work as a brand or a magnet for attention, but ultimately, the quality of your work will reveal that aspect. I often find myself uninterested if the writer does not challenge themselves to explore the unknown. There are only a few narrative novelists capable of writing the same book while ensuring each title remains pure enjoyment. My choices in that category are Richard Stark and P.G. Wodehouse. If you read one book by them, you are likely to enjoy all their other titles. Their exceptional storytelling and beautiful prose keep their work feeling fresh. In contrast, different writers may replicate the same approach but end up with a stale experience, failing to evolve into something unique or undiscovered. 

As a writer, I try to be aware of other writers, both contemporary and from the past, but I never compete with them or wish to emulate them or their work. What I seek, of course, is enjoyment of their writing, but also insights into their skills and the ways they tell their stories. If you write or wish to delve into writing issues, I strongly recommend Lucy Sante’s posts on Substack. I’m a massive admirer of Lucy’s work, and one aspect I appreciate is that you never know where Lucy’s writings will take you. She has a distinctive writing style, yet it's impossible to predict the subject matter fully. If I see the name Lucy Sante on a book cover, I buy the book without looking inside.

Furthermore, when I can debate the value of an author’s blurb on someone’s book, I'm more likely to pick it up if Lucy gives it a like. Her curiosity seems endless, touching on subjects that fascinate me—New York City history, Paris, vintage crime fiction, and memoir. “She’s just a few months older than I am, and her deep musical knowledge feels essential—not just to me, but maybe to others of our generation, too. She covers the waterfront so well.

Sante’s series of posts addresses the subject matter of the English language, or specifically, the American language, including the use of commas, sentence structure, the skills of an older editor, and the breakdown of different types of humor. And there is more, of course, but her sensibility rings so true, and her artistry, along with the charm of her writing, really rubs off on me in a healthy manner.

Lucy Sante’s Substack page is HERE.