I'd rather be wrong and cringe than right and regret not speaking up.
Jon Lovett
Pitzer College Commencement 2013, 2013
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This was Lovett's resolution to the central tension in his speech: the conflict between respecting your own inexperience (lesson one) and speaking up when you see something wrong (lesson two). He acknowledged that these two principles are genuinely in tension and that he couldn't tell graduates how to strike the balance every time. He drew on his experience in the 2008 Clinton presidential campaign, where he and other young staffers sensed that things weren't right — the campaign pollster kept rolling out different slogans while Obama's campaign had just one word: 'CHANGE.' But they were timid, assuming that more experienced people must know what they were doing. The campaign lost, and Lovett drew a lasting lesson he called 'the subway rule: if you see something, say something.' The quote captured Lovett's pragmatic philosophy: the embarrassment of being wrong is temporary, but the regret of staying silent when you were right can last a lifetime.