While Republican managers toss and turn over the prospects of their candidates and the unsettled race, how are the members of Team Obama sleeping?

Well, first, they are sleeping in separate bedrooms. In 2008, it was one big happy family living in Chicago, but now there are two power centers: one in Chicago and one in Washington. This is the result of both natural forces (incumbency) and strains between some of the key players -- inevitable, given the pressure of the last five years of campaigning and governing. This division could be seen in the fight over the debt ceiling. There were those in the campaign who saw Republican intransigence as an opportunity for positioning, while there were those in the White House who sought a deal. But now, no one in the inner circle doubts why they go to work each morning: to re-elect the president.

So what keeps the Obama strategists up at night? Well, I’d guess the two things that matter most: money and message.

First, there’s the fundraising problem. Don’t be fooled by what you’ve read about the success Obama’s been having. As I’ve written before, while small donors on the president’s official re-elect ledger have been willing to give, the president’s super PAC has been having a seriously tough time. This isn’t a reflection of the skills of the fundraisers or strategists; they are among the best. Rather, it signals a reluctance on the part of big donors to go all-in for the president. And if the difficulties continue, it means that the Obama campaign won’t have the money it needs to counter the Republican assault of television ads, defend his record and define his opponent before that opponent gets to define himself.

The other item that’s likely making Obama’s campaign strategists bolt upright in the middle of the night has to do with the vision question. What is the rationale for a second term? And is it better to define the vision as the antithesis of the Republican candidate or to offer a more comprehensive and bold plan for where to take the country? Political operatives working for a battered incumbent almost always choose door No. 1 because the sound-bite driven, cartoon nature of campaign issue discussions don’t lend themselves to any level of detail. Any plan, under this theory, is only fodder for an opponent to distort.

But is this election different? Do the circumstances of the economy require more of answer? Is a proactive vision necessary to reignite enthusiasm for Obama and close the deal? Ultimately, these are questions not just for the strategists but for the president himself.

My head as a consultant says stay away from a bolder vision and try to win ugly. There is no agenda without victory.  But my heart wishes the president would learn from the last three years that winning an election doesn’t necessarily change a thing unless a president has a mandate.