From Newsroom Layoff to Retail Aisle — And a Second Act in Freelancing
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When veteran journalist Caitlin Kelly was laid off from the New York Daily News in 2006, she didn’t pivot to another newsroom — she took a retail job at The North Face at age 50. What started as a way to pay the bills became inspiration for her second book, Mailed: My Unintentional Career in Retail, later praised as “reality journalism at its best.” Since then, Kelly has built a prolific freelance career contributing to outlets like The New York Times, Forbes and AARP.
Kelly encourages freelancers to take a “detailed inventory” of their skills — intellectual, physical and otherwise — and monetize them without worrying about prestige. In today’s shifting media economy, where AI disruption and layoffs are reshaping opportunities, side hustles aren’t a fallback. They’re often the foundation that enables creative freedom, financial stability and even the next big story idea.