Most people think of financial planning as being solely tied to numbers. But a quiet assumption is built into nearly every person’s plan, whether they recognize it or not: They assume the future will cooperate. But life never has been, nor will it ever be, linear.

For many, retirement is an imagined finish line. A date circled on the calendar. A number on a statement. A moment when the alarm clock turns off for good and life finally begins to slow down. Every day becomes a Saturday! And then it arrives.

Where do those tax problems actually show up, and why do so many thoughtful investors ultimately pay more than necessary? In most cases, it’s not a lack of knowledge that drives this problem, but timing. The biggest tax mistake investors make isn’t misunderstanding the rules; it’s waiting too long to act.

Most investors instinctively define risk as market volatility — the uncomfortable reality of stock prices rising and falling over time. When markets drop sharply, the losses feel immediate and visible. Investors see account balances decline, and the headlines only amplify their fear — creating an emotional impact that is powerful and persuasive. But volatility is only one kind of risk.