Everyday Encounters: A writer and a filmmaker diagnose the creative life on Tiburon’s Old Rail Trail

Jenna Smith of San Francisco and her boyfriend, Octavio Kaufman, stop along the Tiburon bike path on Oct. 9. Smith writes a humorous Substack, and Kaufman, whose grandfather directed ‘The Right Stuff,’ makes films and develops scripts. (Tyler Callister / The Ark)

Jenna Smith and her boyfriend, Octavio Kaufman, are walking the Tiburon bike path along Richardson Bay on a brisk morning Oct. 9 when she offers her diagnosis of the creative life.

“It’s a disease,” she says. “We’re too thoughtful and introspective.”

Both are 26, and both spend a lot of time looking within. Smith, a San Francisco resident, is an aspiring writer between jobs — “extremely fun-employed,” she says. Kaufman is a third-generation filmmaker.

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