Financial Planning Mistakes: The Most Risky Moves Aren’t What You Think

Bruce said something on the show that stuck with me because it’s so honest: Everyone thinks they’re an aggressive investor… until they lose money. And it’s true. Most people don’t even realize the biggest financial planning mistakes they’re making until the moment something “unexpected” happens: a market drop, a job change, a medical curveball, an opportunity they can’t jump on because their money is locked away. https://www.youtube.com/live/wp4PzmsvzFQ Bruce also joked that when people go to casinos, nobody ever admits they lost. They either “won” or “broke even.” But those crystal chandeliers weren’t paid for by winners. That’s exactly what happens in real life with money. In the good years, we feel smart. In the up markets, we feel confident. And when everyone around us is sharing their “wins,” it’s easy to believe the biggest risk is simply not being invested enough. But then the market drops. A business hits a slow season. A medical issue shows up. Interest rates shift. Taxes rise. Or the opportunity you’ve been praying for appears—and your cash is locked up, waiting on someone else’s permission. That’s what today’s conversation is about: the sneaky, everyday financial planning mistakes that create real risk—often more than the stock market ever will. What Most Financial Planning Mistakes Really Look LikeFinancial Planning Mistakes Start With Misunderstanding “Risk”Risk tolerance vs risk capacity (and why it matters)Financial Planning Mistakes: Chasing Returns vs Long-Term Financial SecurityThe hidden cost of FOMOThe Safety, Liquidity, and Growth FrameworkHow to balance safety, liquidity, and growth in a portfolioLiquidity Risk in Financial Planning: Locking Money Away Without Realizing ItFinancial Planning Mistakes: Outsourcing Control and Financial Thinking1) Relying on assumptions instead of strategy2) Giving up access and permissionRetirement Planning Mistakes: Why the “Way Down the Mountain” Is HarderWhat is sequence of returns risk in retirement?How to reduce sequence of returns riskTax Risk: Required Minimum Distributions and the Inherited IRA 10-Year RuleRequired minimum distributions tax planningInherited IRA 10-year rule taxes (SECURE Act)How to Minimize Risk: Whole Life Insurance Cash Value - Liquidityand Legacy ProtectionWhole life insurance as a volatility bufferA personal note on why this mattersWhat to Remember and What to Do NextListen to the Full Episode on Financial Planning MistakesFAQWhat are the most common financial planning mistakes?What is sequence of returns risk in retirement?How do you define risk tolerance vs risk capacity?Why is liquidity important in financial planning?How do required minimum distributions create tax risk?How does the inherited IRA 10-year rule affect heirs?Can whole life insurance reduce portfolio risk? What Most Financial Planning Mistakes Really Look Like When most people hear the word “risk,” they immediately think of market volatility. The stock market goes up and down. Inflation eats purchasing power. Taxes change. Interest rates rise. Those are real risks. But they’re not the only risks—and for many families, they’re not even the biggest ones. Some of the most risky moves in financial planning are the ones that feel “normal”: Chasing returns because you don’t want to miss out Locking money away without liquidity Relying on assumptions instead of strategy Outsourcing too much control and decision-making Ignoring tax risk until required minimum distributions force your hand Building retirement plans without accounting for sequence of returns risk This post is designed to help you identify the financial planning mistakes that quietly erode your financial strength. You’ll also learn a simple framework—safety, liquidity, and growth—that makes decisions clearer, and helps you reduce risk in ways most financial conversations never touch. If you want more control, more flexibility, and more confidence in your future, this is for you. Financial Planning Mistakes Start With Misunderstanding “Risk” Risk is a subjective word. What feels risky to you might feel normal to your friend, your neighbor, or even your spouse. People in the same family can interpret “risk” in completely different ways. That’s why generic risk questionnaires often miss the point. They may score your “risk tolerance,” but they can’t fully capture how you’ll actually respond when real money is on the line and emotions show up. One of the clearest ways to surface what risk truly means to you is to compare two types of risk most people don’t realize they carry: The risk of losing money (or seeing your account value drop) The risk of missing upside (watching the market rise while your portfolio lags) Here’s a simple question that cuts through the noise: If the stock market goes up 20% and you only go up 5%, does that make you feel worse than if the market goes down 20% and you go down 20%...