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There are conversations we avoid because they hit too close to home money, domestic violence, poverty, and the quiet realities of single parenthood. In our first guest episode of 2026, I sat down with Cindy Wittemann, and let me just say it: this woman is a powerhouse with a story that carries both pain and proof. She grew up in deep poverty with a single mom sometimes without electricity, water, food, or transportation and as a child she attached “success” to the simplest things: a fridge with food, lights that turned on, a roof that didn’t feel uncertain. So she did what so many of us were taught to do she believed marriage would be her escape hatch. Her happily-ever-after. Until it wasn’t. Ten years into a domestic violence marriage, raising three little girls, she heard one sentence that cracked the illusion wide open: “It’s better to come from a broken home than grow up in one.” And that day, Cindy picked up a basket of clothes, a bag of diapers, her babies three, two, and five months and she left. What hit me hardest wasn’t just her courage to walk out. It was the clarity around why she stayed so long: the stigma. The story she carried from childhood that single parenthood meant failure, poverty, shame, and “ending up like her mom.” And like so many abusive dynamics, her spouse used that fear as a weapon If you leave, you’ll be broke. You’ll be on welfare. You’ll be exactly like her. This is why we have to talk about money. This is why we have to talk about single parenthood. Because the belief systems we inherit as children don’t just shape our choices they can trap us inside lives we were never meant to survive. Cindy’s nonprofit grew from that exact reality: the “messy middle” families who don’t qualify for enough help to get ahead, yet can’t access the next level because the system penalizes growth. She gives single parents cars—not as charity, but as a tool for forward motion. A way to reach school, work, childcare, and opportunity. Because poverty isn’t always laziness it’s often logistics, red tape, and a system that makes “one dollar more” cost twelve hundred dollars in lost support. Cindy said it so simply it took my breath away: “I see you.” I see how hard you’re working. I see the sacrifice. I see the bravery it takes to keep showing up when you’re carrying everything alone. Because leaving isn’t the easy way out staying is often the familiar cage. And if you’re in that place today unsafe, unhappy, trapped by fear Cindy offered a truth that lands like a dare: Whether you think you can or you think you can’t… you’re right. Sometimes courage looks like therapy and a plan. Sometimes it looks like selling plasma and working two jobs. Sometimes it looks like one shaky step with no map at all. But there is another side. And one day your kids will look at you and say, “How did you do that?” And you’ll realize: you didn’t do it perfectly. You did it honestly. You did it anyway.