Imagine saving nearly your entire paycheck while your rental properties cover your bills. That's exactly where real estate investor Andrew finds himself — and yet he's at a crossroads. At FinCon, a personal finance conference, former financial advisor Joe Saul-Sehy and I sit down with Andrew and another attendee who bring their money dilemmas live on stage. Andrew's question seems simple at first: should he sell his index funds to pay off his rental mortgages? But the real story runs deeper. He feels called to entrepreneurship and wants to quit his corporate job to pursue it full-time. He could achieve minimal financial independence (lean-FIRE) if he pays off the properties, but that might limit his options. Next, Chris, a Gen X dad, opens up about his Gen Z kids' gloomy money outlook. His 22 and 24-year-old children, especially his daughter, believe their generation "will never retire." They see high inflation, expensive housing, and low wages as insurmountable obstacles. This sparks a deeper conversation about generational perspectives. We note that similar fears existed 15 years ago when millennials entered the workforce during the Great Recession. Joe shares how he helped his own kids develop healthier money mindsets by introducing them to financial voices they could relate to, like Broke Millennial author Erin Lowry. The discussion evolves into how today's young people actually have more opportunities than previous generations — they can work remotely, start online businesses with minimal capital, and create multiple income streams through platforms that didn't exist before. Chris's daughter, for instance, sometimes makes $35/hour driving for DoorDash during peak times. We wrap up by talking about the importance of focusing on what you can control and finding purpose beyond just retirement planning. As Andrew points out, it might be worse to spend the best years of your life doing work you don't care about than to face uncertainty in retirement. The key is taking action on the things within your control while building toward long-term security. Throughout the conversation, both guests share personal stories that illuminate their situations - from Andrew's experience at an oil refinery that pushed him toward entrepreneurship to Chris's daughter storing cash for taxes from her DoorDash earnings, showing she's more financially aware than she might think.

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