Cody Keenan, President Obama's chief speechwriter, shared a moment of private mentorship from the Oval Office. He had handed Obama a draft of a major speech, and the President called him back thirty minutes later. Obama started by saying the draft was 'well-written' and he could 'probably deliver it as is' — which, Keenan noted, almost never meant he actually wanted to. Then Obama gave him the best piece of advice he'd ever received: 'You took a half-swing on this. Take a full swing.' Keenan admitted Obama was right — he had played it safe out of fear of how people would react. But they had never regretted going big, provoking uncomfortable conversations, or poking holes in political BS. Fear of failure had reined him in, when usually it propelled him forward.