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In this episode, I sit down with financial planner Taylor Stewart for one of the most honest conversations I’ve had about money, uncertainty, and what real financial planning should look like. We talk about the messy reality of life, diapers, dogs, spilled coffee, bad first dates, and why those imperfect moments actually mirror how most of us handle money. Taylor shares how growing up around financial planning gave him one vision of the profession, only to discover later that much of the industry is built around selling products instead of giving real advice. That realization pushed him to build a new approach to planning, write a book on embracing uncertainty, and even create software that helps advisors focus on action instead of pointless precision. We dig into why people get paralyzed trying to make perfect financial decisions, how optimization anxiety keeps us stuck, and why progress always beats perfection. Taylor explains why investments are overemphasized, liquidity is ignored, and why staying alive financially matters more than chasing home runs. We explore uncertainty as a necessary part of growth, from saying yes to scary opportunities to increasing the surface area for luck in life and business. Along the way, we talk credit cards, behavioral traps, gamified finance, building healthy money habits, and teaching kids financial principles through zombie apocalypse survival planning. This episode is for anyone who has ever felt overwhelmed by money, frozen by too many choices, or frustrated with traditional financial advice. It’s about stepping back, focusing on what you can control, and building a life where your money supports your goals instead of stressing you out.