Oops! I Did It Again.

Why Obama’s “big mistake” was really just a humblebrag.

President Barack Obama
President Barack Obama

Photograph by Saul Loeb/AFP/GettyImages.

“Presidents cannot admit mistakes,” a senior Bush administration official once told me. Admitting mistakes makes a president look weak, gives critics ammunition, leads to more questions, and sets a dangerous precedent for the next time everything doesn’t go to plan. Once you’ve admitted a mistake, where do you stop? You definitely don’t want to admit a mistake in an election year. So when Charlie Rose showed up at the White House asking the president what he thought his big mistake was, all that remained a mystery was how Obama would evade the question.

President Obama chose the humblebrag: “The mistake of my first term—couple of years—was thinking that this job was just about getting the policy right. And that’s important. But the nature of this office is also to tell a story to the American people that gives them a sense of unity and purpose and optimism, especially during tough times.” 

This is a shame. Recognizing mistakes and knowing how to fix them is a key attribute of the presidency. The only way voters know that a candidate or president has this skill is if they talk about it. In our campaigns, we condition candidates to never reveal any mistakes, second guessing, or lessons they’ve learned through trial and error. Our campaigns are like an Olympic qualifying trial in which contestants are not tested for the sport they’ll ultimately play. 

The president was essentially saying that he was working so hard trying to help the American people, he forgot to tell them about it.

Candidate Obama had a laugh about the humblebrag in 2008. At a Democratic primary debate, the candidates were asked to name their biggest weakness. Obama said he was messy and had trouble keeping up with paperwork. Not very revealing, but not a humblebrag. Hillary Clinton and John Edwards both offered versions of the humblebrag which irked Obama. “Folks, they don’t tell you what they mean!” he joked the next day. “I thought that they meant, ‘What’s your biggest weakness?’ So I said, ‘Well, you know I don’t handle paper that well, you know, my desk is a mess, I need somebody to help me file and stuff all the time.’ So, the other two, they say, ‘Well, my biggest weakness is I’m just too passionate about helping poor people. I am just too impatient to bring about change in America.’ If I had gone last I would have known what the game was. I could have said, ‘Well, you know I like to help old ladies across the street. Sometimes they don’t want to be helped. It’s terrible.’ “

Though the president now knows the game, he has—even if fleetingly—offered actual contrition. He admitted early in his tenure that he mishandled the nomination of Sen. Tom Daschle. “I screwed up,” he said at the time, explaining that his seeming indifference to Daschle’s tax problems sent a message that the powerful are treated differently than average people. And what he said this week to Charlie Rose is not a pure humblebrag—fake humility designed to make you look better—for which we should punish with public floggings. The president was likely being sincere. He honestly believes that his communication could have been better. 

How you react to this comment depends on where you sit. To the president’s critics, it sounds patronizing. I was doing the right thing, but the slow American people didn’t get it. For his fans, the president is embracing a critique they’ve made all along: What happened to the great orator of the campaigns? For students of the rhetorical presidency, Obama’s focus on the centrality of words will seem anywhere from curious to laughable. Presidents don’t win the country through stories; it’s the policy that determines how people feel. 

Wherever you stand on the question of the power of rhetoric, there is a far more interesting list of mistakes that the president could have discussed: He overestimated the power of the stimulus, he took his eye off the ball by pursuing near universal health care at the expense of the economy, he tried for too long to win bipartisan agreement, or he didn’t try hard enough. 

The president is not alone. Mitt Romney says he has made mistakes, but he doesn’t really talk about them. He has his own version of the humblebrag. He says when he was CEO of Bain he didn’t think JetBlue was a good investment. Romney was a wildly successful businessman, so this is a bit like a 450 hitter talking about a strikeout. Newt Gingrich took the form to a hysterical extreme when he explained that he had been unfaithful to his ex-wife because his desire to improve the country had put so much strain on him that he strayed. 

Politicians are interested in self-preservation. So the false modesty isn’t surprising. But these answers rob us of so much that might actually help us evaluate our candidates. Imagine what a little public introspection might do: It would be a shock of candor that might wake the sleeping ears of the electorate. That would simply be refreshing. (And who doesn’t want refreshment in this summer heat?) Voters might listen to a candidate who showed he was different by taking a little risk. (This means President Obama is making a compound error: He’s missing the rhetorical opportunity by saying that his mistake was that he missed rhetorical opportunities.) 

In the presidency, in particular, it’s hard to get good advice about your failures because so many people who work for you are awed by the office. Or they are in such a permanent state of partisan siege that they stay quiet for the sake of the cause. (Former Democratic governor of Pennsylvania Ed Rendell is the exception; he seems to identify a new mistake Obama is making every day). A candidate’s ability to see mistakes suggests they can tolerate candid advice from subordinates, which could short-circuit extended calamity. Presidents are criticized all day long. How they know what’s worth ignoring and what’s worth heeding gives us insight into how good their judgment really is.

There are countless aphorisms on coffee cups, inspirational posters, and daily calendars devoted to the benefits of failure as a learning device, but our candidates will never show us how they have reaped those benefits, or more important, whether they’re able to find benefit in failure at all. We should know if they are pig-headed, obstinate, or willing to “stay the course” out of psychological neediness. 

Ronald Reagan put all of this nicely: ”What should happen when you make a mistake is this. You take your knocks, you learn your lessons, and then you move on. That’s the healthiest way to deal with a problem. You learn. You put things in perspective. You pull your energies together. You change.”

Reagan was admitting that his administration had tried to trade arms for hostages. His is among the few modern presidents to admit he made a mistake. Kennedy took his lumps after the Bay of Pigs, too. Those two cases were extreme. Each man had to do something to recoup their reputation after a devastating blow to their administrations. Perhaps it’s a sign of political health for Obama that he hasn’t been forced to apologize for any huge disaster. 

For anyone who has watched the current campaign fishtail from one absurd, out-of-context gaffe to another, the president’s dodge probably seems smart. Self-reflection might be lovely and desirable, but self-immolation is dumb. Obama is not running for president in a therapy session full of compassionate listeners. He’s running in whatever is the polar opposite of that. So we’ll just have to take it on faith that he and his opponent know how to handle mistakes. Because we generally only learn if they can admit that they have made a mistake when it’s a really big one.