Tonight at the Democratic National Convention, President Obama will have his swan song of sorts with his fans, the last big campaign venue (well, not as big as it was going to be, but still) for him to try to wow a friendly crowd and compliant press corps. Sure he’ll campaign until November, but this is almost certainly the last campaign event in which he will have a mass audience live and on TV.

Trying to re-create the 2008 experience for his supporters has backfired in part because the reelection is never so exciting as the first go-around, especially with a president lauded as a “historic” figure and then panned for a poor term. In his presidency he never has hit the rhetorical uplift of the 2008 campaign. He has too often been peevish, frustrated or dismissive of his opponents. Can he return to no-red-states-no-blues-states rhetoric after so much divisive rhetoric? Well, he can try.

I’m not sure what he would have said before the events of this week, but it seems that Obama has several new challenges that require his attention.

He now will have to answer the “Are you better off?” question and give his answer as to why the economy is still so rotten. Considering how poorly things have been going, it would be odd not for him to recognize that millions and millions of Americans are unemployed or underemployed. In his most recent interview he said we are absolutely better. He can make that case. But even if he gets over that hurdle, why aren’t we much better?

He could blame George W. Bush or the Republicans or someone else, but the danger in complaining about others and the limitations of his office is that it becomes an argument against giving him four more years. (There will still be Republicans, right? He’ll still face all those “special interests.” Europe will still be an economic basket case.) Walking the fine line between confidence and cluelessness is not easy, especially for a president who has become a poster child for underachievement.

He’s also going to have to tell us what he is going to do to meet the challenges he didn’t address in his first term. It simply isn’t credible to say that raising taxes on the rich, hiring more teachers and throwing some more stimulus money (because the original money was poorly spent) at infrastructure are the answers to our fiscal and economic woes. The pundits keep insisting he pony up his proposals, plans and policies. Well tonight is now or never — does he have any that are commensurate with our problems?

Next, he’ll have to decide if he is going to return to rhetorical uplift or try to savage his opponent on national TV. To be honest, Mitt Romney is probably enjoying this week as much as his own convention, in part because the attacks against him have become mundane and the distractions at the Democratic convention have sucked up some of Obama’s oxygen.

It is one thing, however, to have super PACs and surrogates call Romney every name in the book; it’s quite another for the president to do it himself. And doing so would be quite an admission that he can no longer win with voters for Obama but must win with votes against Romney.

He’ll also need to fix his Israel problem, which has become an embarrassing debacle. What is his position on Jerusalem, and is that his administration’s position? What’s the problem with declaring that we should isolate Hamas or that Palestinians should have no right of return (positions he took in 2008)? That he must still argue he has “Israel’s back” is a sign of how poorly things have gone internationally (as he has been trying to wave Israel off unilateral action against Iran) and even within his own party convention. It is not clear what he can say that would reassure voters concerned about the U.S.-Israel relationship, but if he avoids the topic he will be pilloried. Again.

And finally, he’ll have to decide whether he wants to defend himself on Medicare and welfare. He has never given a coherent defense of his decision to double-count money to pay for Obamacare and for Medicare, nor has he explained why the welfare work requirement had to be changed. If he avoids those topics, surely the Romney-Ryan team will call him out. If, however, he spends excess time explaining himself the speech will be defensive and unlikely to inspire.

Recall that the Obama’s game plan all along has been to destroy Romney as a viable alternative. He hasn’t done that, and it is now September. Romney’s favorable ratings are up, and the race is essentially a dead heat. So what does he do now? The speech tonight will answer that to a large degree. We should find out how an unsuccessful president with no (as of yet) big policy plans intends to persuade voters to reelect him. Is there something there besides vilifying his opponent?