Jen's WASPy money upbringing

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"The number one question I get at my talks is, what do you do when the people closest to you don't support your growth? The main reason they don't support it is because you're killing off the person they love." - Jen Sincero

Jen Sincero sat in the driver's seat of an Audi she couldn't imagine owning, convinced the salesman would recognize her as an imposter and kick her out. She said "I can't afford it" so automatically it became a reflex, spoken a hundred times a day like a prayer to poverty. But those three words weren't just describing her reality—they were building it, brick by brick. Every time she said them, she pulled in more proof: the terrible car, the alley apartment, the bank account that never grew. She was trapped at what she calls the "kid table financially," watching real adults with real money from a distance, like they belonged to a different species. The shift didn't come from budgeting tips or side hustles. It came from understanding something most people never grasp: comfort zones aren't comfortable at all. They're familiarity zones, and breaking out of them requires something violent and necessary—killing off your old identity completely.

This conversation cuts through every sugar-coated personal development cliché about money mindset. Jen talks about the WASP household where money was dirty, the rock-and-roller identity where wanting wealth meant selling out, and the brutal realization that to make real money, you have to obliterate the version of yourself that can't. Lewis and Jen dig into why this transformation is so lonely, why the people who love you often resist your growth hardest (you're literally killing off the person they know), and what it actually takes to shift from someone who can't afford things to someone who can. If you've ever felt stuck financially while watching others succeed, if "I can't afford it" comes out of your mouth more than you'd like, or if you're trying to grow and finding your closest relationships straining under the weight, this one will shake something loose.

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