“Now it’s a knife fight for every job,” he said. “The cruel irony is, the thing I perceived as the sellout move is in free-fall.”
He decided to recommit to his first love. The result, the documentary “Flipside,” released last year, is a personal film about the trade-offs required to support yourself as an artist. In it, he weaves together footage from his unfinished projects while grappling with his career choices in a wry voice-over narrative.
For the theatrical release, he worked with Oscilloscope, an independent distributor founded by Mr. Yauch of the Beastie Boys, and he often presented the film himself.
“It felt very ’90s,” he said. “It was that indie rock model: Get in the van, tour with the thing, get bodies in the seats. It made no money. But what it did do — and this is what I believe as a Gen X creative person — it confirmed my belief that continuing to make stuff is the path forward.”
Mr. Gentile, the former photo studio manager at Condé Nast, went through something similar. The company was cutting costs as the consultancy McKinsey & Company roamed the halls, and he came face to face with his own irrelevance. He was 40, with an artistic background.
“Who would hire me?” he thought. “Maybe this is where I jump off.”
As a sideline, Mr. Gentile, an avid surfer, had opened a surf shop, Pilgrim, in Williamsburg, Brooklyn. He quit his day job and dedicated himself to the store. He and his wife, Erin Norfleet Gentile, have since expanded it into a clothing brand.
“One thing I’m grateful for, and it’s a strength of my generation, is we weren’t promised anything,” Mr. Gentile said. “I was prepared to struggle.”
Mr. Kandell, the former magazine editor, also had a reckoning.
After Spin stopped appearing on newsstands, he took a job at BuzzFeed, the news and entertainment site that was seen as the future of media at the time. By 2017 BuzzFeed was just another struggling outlet that was doing mass layoffs. Mr. Kandell, then in his mid-40s, married with a child, left for another media outlet. His wife also worked in media.
“Then we had a second kid, and we lived in a small New York apartment,” he said. “And it felt like the only thing we and our friends talked about was, ‘Well, what now’?”
He and his family moved to California, where he took an editorial position at a tech company. The job gave him some security and allowed him to contemplate a second career.