Even though his second inauguration is still weeks away, the work of his presidential library starts soon: Libraries take years of planning and decisions by the president and his inner circle, from choosing a location, to picking achievements to highlight. It’s a chance for Obama to begin shaping his legacy, and has in the past been an increasingly large priority during presidents’ second terms.

But it requires the kind of personal fundraising that Obama clearly dislikes, full of potential pitfalls that led his predecessors into trouble.

Add more complications for Obama: He’ll have to decide whether to build the library in his birthplace of Hawaii or his adopted hometown of Chicago and possibly raise funds for a presence in both. Even for one, he could need to raise close to $500 million. Though much of the work will be done by a circle of close friends who will begin mobilizing in the coming months — including one longtime friend of the first lady already starting to make way for the library to be associated with the University of Chicago — much of the fundraising is going to come down to Obama himself.