If foundation regrets arise from the failure to plan ahead, work hard, follow through, and build a stable platform for life, boldness regrets are their counterpart. They arise from the failure to take full advantage of that platform—to use it as a springboard into a richer life. Sometimes boldness regrets emerge from an accumulation of decisions and indecisions; other times they erupt from a single moment. But whatever their origin, the question they present us is always the same: Play it safe or take a chance?