On this episode of Simply Money presented by Allworth Financial, Bob and Brian explain why the most expensive financial decisions often aren’t the ones you make — they’re the ones you avoid . They walk through real-life examples of high-net-worth families who delayed portfolio changes, tax planning, diversification, or retirement decisions, only to face bigger consequences later. The guys also break down why a “good investment” can still be a bad financial move if it increases concentration risk or limits liquidity, key questions to ask before retiring early, how to think about withdrawal strategies and portfolio drift, and one clear sign you may be overthinking your finances.