The following video is part of our "Motley Fool Conversations" series, in which senior analyst Anand Chokkavelu, CFA, discusses topics across the investing world.

Timing the market is a dangerous game. Whether it's the housing market or the stock market, making prudent fundamentals-based decisions is better than trying to go "all-in" when situations look favorable. In his latest shareholder letter, Berkshire Hathaway's Warren Buffett shows how difficult predicting the timing of the market is with a failed housing market prediction from last year. Anand explains.

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This article represents the opinion of the writer, who may disagree with the “official” recommendation position of a Motley Fool premium advisory service. We’re motley! Questioning an investing thesis -- even one of our own -- helps us all think critically about investing and make decisions that help us become smarter, happier, and richer.