WASHINGTON • The dinner in the private upstairs dining room of the White House went so late that Mr Reid Hoffman, the LinkedIn billionaire, finally suggested around midnight that President Barack Obama might like to go to bed.
But Mr Obama was just getting started. "I will kick you out when it is time," he said.
He then lingered with his wife, Michelle, and their 13 guests - among them, novelist Toni Morrison, hedge fund manager Marc Lasry and Silicon Valley venture capitalist John Doerr - well past 2am.
Another guest, writer Malcolm Gladwell, recalled how the group, which also included actress Eva Longoria and Mr Vinod Khosla, a founder of Sun Microsystems, tossed out ideas about what Mr Obama should do after he leaves the White House.
"Where we will end up, I don't know yet," said Mr Marty Nesbitt, the President's longtime Chicago friend who is leading an extensive planning effort for Mr Obama's library and an anticipated global foundation.
"I haven't projected out 10 years. I know what I will do right after the next president is inaugurated. I will be on a beach somewhere drinking out of a coconut."
PRESIDENT BARACK OBAMA, on what he will do after he leaves office
Publicly, Mr Obama betrays little urgency over his future. Privately, he is preparing for his post-presidency with the same fierce discipline and fund-raising ambition that characterised the 2008 campaign that got him to the White House.
The long-running dinner in February was part of a methodical effort as the President, First Lady and top aides map out a post-presidential infrastructure and endowment they estimate could cost as much as US$1 billion (S$1.4 billion).
The US$1 billion - double what Mr George W. Bush raised for his library and its various programmes - would be used for what one adviser called a "digital-first" presidential library loaded with modern technologies, and to establish a foundation with a worldwide reach.
Supporters have urged Mr Obama to avoid the mistake made by former president Bill Clinton, whose associates raised just enough money to build his library in Little Rock, Arkansas, forcing him to pursue donors for years. Mr Obama has so far raised just over US$5.4 million for a foundation to oversee development of the library.
His recent visit to a federal prison indicates, advisers say, a likely emphasis on criminal justice reform after he leaves office. His eulogy for one of nine African-Americans killed at a church in Charleston, South Carolina, is a forerunner, they say, of a focus on race relations. Diplomacy with Iran and Cuba could serve as the foundation for foreign policy work.
"His focus is on finishing this job completely, thoroughly," said one of Mr Obama's closest confidantes, Ms Valerie Jarrett.
However, officials said the President's thinking on some of his signature issues - including healthcare, economic inequality and climate change - also involves considering their part in his life after January 2017.
The process started as early as the week after Mr Obama's re-election in 2012, when film director Steven Spielberg and actor Daniel Day-Lewis went to a White House screening of the movie Lincoln.
Mr Spielberg held the President spellbound, guests said, when he spoke about the use of technology to tell stories. Advisers say Mr Spielberg has focused on helping to develop a "narrative" for Mr Obama after he leaves office.
At a dinner this year in San Francisco, Mr Obama urged technology executives to focus their philanthropic efforts on helping government become more efficient, giving some the impression that the topic will most likely be a theme of his agenda after leaving office.
Among the debates at some of Mr Obama's dinners: How can technology be used to provide global access to his presidential library? How prominent should Mr Obama seek to be, especially in the first few years of his post-presidency.
The next milestone in the library planning will come this month when foundation officials kick off a global search for an architect. The Chicago library will include an office for the President, but aides said the Obamas could live in Washington while Sasha, 14, their younger daughter, finishes high school.
The President, who graduated from Columbia University, may also have a New York office.
In an interview on the website Tumblr, Mr Obama was asked what he expected to be doing in 10 years' times. He took more than 30 seconds to respond. "I haven't projected out 10 years," he said. "I know what I will do right after the next president is inaugurated. I will be on a beach somewhere drinking out of a coconut." NEW YORK TIMES