Plant the Flag

Matt reads a Business Insider piece on Kara Swisher — the tech journalist who went from the Washington Post and Wall Street Journal to building her own independent media identity through Recode, podcasts like Pivot, and books — because her counsel to journalists leaving downsizing institutions applies to anyone making that leap. And it’s happening far beyond journalism: people who earned multiple six figures inside big institutions are heading out on their own, voluntarily or not, and discovering that a half-million-dollar salary and a “please subscribe for $12 a month” Substack are entirely different games. Swisher’s advice, notably, is not “follow your passion.” It’s assess your risk tolerance, keep skills that are always saleable, sense what audiences will want before they ask — and, above all, have something distinctive to say. That last one is where Matt digs in. You rarely get to say something genuinely new, but you can be distinctive — substantively (going against a common belief) or stylistically (the way you deliver it, the way a drug company engineers whether a treatment arrives as a pill or a shot). The hard part, especially for people whose muscle was built in collaborative or diplomatic corporate settings, is planting a flag on a real position and defending it. A point of view sharp enough to break through will attract people who fight you and leave nasty comments — and Matt’s tell is that the faster and more reptilian the reaction, the less thought behind it. That comes with the territory. Draw on the credibility and relationships you earned over decades, then get comfortable saying what you actually think, a bit more candidly and fearlessly than felt allowed before. His closing question is the sharpest distillation yet of the theme he keeps circling: if your former title disappeared, what still makes someone curious about you? The substance is there, he promises — put the prompt to your mind, go for a walk, and let it surface. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit mattstone.substack.com