Mitt Romney is making two mistakes in this presidential race. His first mistake is that he thinks that he's tougher than Barack Obama because he's a businessman, and Barack Obama is a politician, and business people are tougher than politicians. His second mistake is that he expects the American people to automatically give him greater respect and deference because of that. He expects that when he says that something is true, or he gives his perspective on how events unfolded in his life, his explanation will be accepted at face value.
My favorite example of people in business making this mistake of thinking that they are tougher than people in government is a tech company (I think it was Microsoft) that was being sued by the US Department of Justice. The Microsoft folks assumed that they were much tougher than the dweeby government lawyers, because they operate in the hypercompetitive environment of the computer industry, whereas government lawyers are bureaucrats who spend their hours trying to figure out how to interfere with businesses making money. What the Microsofties forgot was that prosecutors at the DoJ deal with foreign intelligence agencies (remember the KGB?), Mafia kingpins, drug lords, and other people who will lie, cheat, steal, and kill to achieve their goals. On a toughness scale, Microsoft's competitors - geeks with fast calculators who drink too much coffee - do not compare well to spies, assassins, and gangsters. Steve Jobs was a tough competitor. Unless you compare him to, say, Saddam Hussein, John Gotti, or the Soviet Union.
What people in business fail to appreciate is that they spend most of their time with people who agree with them, whereas politicians spend a lot of their time with people disagree with them. Most people in business do not have daily, direct contact with their competitors. They spend most of their time with people in their own company, with whom they have common goals. Or they spend time with their customers or vendors, people with whom they are trying to reach a mutually satisfactory accommodation. It's not necessarily easy negotiating with your co-workers, customers, or vendors. But those people generally are not doing everything in their power to stop you from achieving your goals. They may disagree with you, or even dislike you. But they're not out to destroy you. Your competitors may be trying to do that. But you don't have to deal with them literally face-to-face every day. And they rarely make it personal. In business, it's perfectly legitimate to question a competitor's product or strategy, but it's off-limits to attack their character.
The Democrats are going to attack every facet of Mitt Romney's experience, in the public and private sectors, in a way that none of his competitors in the private sector ever did. They're going to raise as many questions about his character as they possibly can. It's a nasty, unpleasant business, but anyone who thinks that the practice of democracy is all about the grandiose articulation of principles has done a very selective reading of history.
This is where Romney's second mistake is potentially fatal. The Democrats are going to raise questions in the minds of voters, and a fair number of voters are going to consider those questions legitimate. Mitt Romney is having trouble answering questions like when did he actually, officially, really, truly, honest-to-God-cross-my-heart leave Bain Capital, because he has never had to face those questions before. He has lived his life according to these precepts: the explanations of him and his lawyers will always be sufficient to answer questions about whether or not his actions were proper. If he signs a piece of paper, he and his associates have cleared it with the lawyers, so it's OK. Period, end of story. He simply has no experience with people who do not automatically accept his ability to explain fine legalistic details of his professional life. He assumes his own credibility, so he has no idea how to establish that credibility. His lawyers have both assumed that credibility as well, and worked hard to prevent anyone from even raising any questions about it. Mitt Romney has always had people around him who ran interference for him on questions of legality. It's been a closed loop; he hired people who assumed that what he was doing was legal and proper, and they then kept him in a bubble of legality and propriety. He's never had to question his own assumptions. So the Democrats are doing that for him.
Professional politicians, however, operate on the assumption that they will be questioned on those details, and they will have to explain them. They know they will be expected to release their tax returns. They know that their personal credibility is something that they have to establish very carefully, and then work very hard to maintain. They deal on a day-to-day basis with people who questions their assumptions and their legitimacy.
Mitt Romney thinks that he, the son of a wealthy father, who had every possible advantage in life and who has spent most of his life surrounded by people who are very much like him, and who think like him, is tougher than the son of a single mother who had to use his own personal discipline and focus to rise to the highest levels of a society that, not so long ago, erected substantial barriers to success for people like him. Mitt Romney's formative experiences were in offices and boardrooms. Barack Obama's formative experiences were on the streets of Chicago. Mitt Romney may never realize that he has substantially underestimated how tough Barack Obama can be. But even if he realizes it tomorrow, it will probably be too late.
One of the toughest jobs in the world is selling yourself to someone who doesn't necessarily trust you, particularly when they can choose an alternative with one simple push of a button. Welcome to American politics on the national stage, Mr. Romney.