In a speech to handful of loyalists and donors Wednesday night, President Obama made clear the grand experiment he is embarking on with the creation of a new grassroots operation known as Organizing for Action.

President Obama's grand experiment. AFP/Getty photo

"Can we sustain the sense of citizenship that arose during the course of the campaign outside of a campaign structure, outside of the immediate, okay, we're trying to win this many votes in this many states, but can, instead, we activate people around an agenda," Obama asked the crowd.

Put simply: Can Organizing for Action find a way to mobilize the millions of people who signed up to be a part of his campaign on behalf of his legislative priorities?

Obama has tried and failed to do just that once before. Following his 2008 victory, he created Organizing for America -- an entity within the Democratic National Committee aimed at converting the energy of his campaign to support for his legislative agenda.

While OFA proudly touted the hundreds of thousands of phone calls it made and doors it knocked on to back Obama's policies, it was not regarded as anywhere near as successful as the campaign had been when it came to actually mobilizing people and driving an agenda.

Obama, for the first time we can recall, admitted as much during his remarks on Wednesday.

"What we don't want to do is repeat the mistake I think that I believe in 2008 we made where some of that energy just kind of dissipated and we were only playing an inside game, and I'm sitting in a room with a bunch of folks negotiating all the time but those voices are no longer being heard," Obama said.

That's far easier said than done, of course -- for two reasons.

1. Campaigns are sexy. Legislating is not. Campaigns -- at least the good ones -- are built on getting people to buy into the idea of a brighter future, the idea that anything is possible. It's the part of politics that people love, appealing to the dreamer in all of us.  Legislating -- even at its best -- is grinding and ugly. (Watch "Lincoln" if you need an example. Not much has changed since then.)  It's easy to get excited about a campaign. It's hard to get excited about legislating.

2. Movements need a man (or woman). Campaigns are, by their nature, centered on the candidate. That's why they work. Human nature is such that we like to have a person to connect with, not just an idea or a message. The messenger is critically important to people consuming (and sharing) the message. While Obama is quite clearly affiliated with Organizing for Action -- his speech Wednesday night being a prime example -- he won't (and can't) be as closely aligned with the organization as he was with his two presidential bids.

Given those challenges, it's not too much to say that Obama -- along with top campaign aide Jim Messina -- is in uncharted political territory with Organizing For Action. It's a bold stroke to transform a political organization built in a campaign setting into a policy (and political) organization that stands outside of the campaign framework. No one has done it before -- and even Obama has tried and failed.

Succeed and his legacy, politically speaking, will be further bolstered. Fail and it will be yet another example of how hard it is to take campaign successes and turn them into legislative ones.