Obama gives clearer view of post-White House life

Obama makes final appearance on 'The Late Show'
Obama makes final appearance on 'The Late Show'

    JUST WATCHED

    Obama makes final appearance on 'The Late Show'

MUST WATCH

Obama makes final appearance on 'The Late Show' 01:04

Washington (CNN)When President Barack Obama‎ sat down last week with the outgoing late-night host David Letterman, he joked the two would play dominoes together in their upcoming retirements.

But if Obama's ever-more active planning for his post-presidential days is an indication, a quiet life of shuffleboard and early-bird specials doesn't appear in the works.
After leaving office in 2017 -- 10 years before reaching the federal retirement age -- Obama will still have decades to advance parts of the agenda he's developing for himself. And while his aides insist Obama is as focused as ever on the here-and-now job of running the country, his decisions as President are beginning to hint at his desire to cement a legacy for himself long after he departs the White House.
On race -- a topic on which his legacy in some ways is already fixed as the first African-American president -- Obama and the first lady have become more and more candid in the waning days of the Obama administration.
    On Tuesday, Obama told a forum on poverty that he makes no apologies for speaking personally about his own experiences growing up as a black man without a father.
    "I know the costs that I paid for it," he said. "And I also know that I had the capacity to break that cycle, and as a consequence I think my daughters are better off. "
    Michelle Obama spoke in just as plain terms on Saturday about the anxieties that came along with becoming the first black First Lady.
    "Was I too loud or too angry or too emasculating?" she wondered. "Or was I too soft, too much of a mom and not enough of a career woman?"
    Last week Obama re-launched his My Brother's Keeper initiative as a non-profit organization, with millions of dollars in commitments from private firms and a high-wattage roster of board members. He said the program's work on establishing mentorships and increasing access to good education for young minority men would remain his focus "for the rest of my life."
    Meanwhile, the Obama presidential library -- the physical embodiment of his legacy -- has found a home on Chicago's South Side, with fundraising for the $500 million project set to ramp up soon.
    Obama nominates new Joint Chiefs chairman
    lv bts obama nominates dunford joint chiefs chairman_00023103

      JUST WATCHED

      Obama nominates new Joint Chiefs chairman

    MUST WATCH

    Obama nominates new Joint Chiefs chairman 02:33
    Even Obama's hiring choices are beginning to hint at what the current President hopes to bestow upon his successor: his pick for chairman of the Joint Chiefs of Staff, Gen. Joseph Dunford, has helped orchestrate Obama's drawdown of troops in Afghanistan, a prolonged process the President hopes can continue when the next commander-in-chief takes over.
    If Dunford is confirmed by the Senate, his two-year term will extend past Obama's own departure date, meaning he'll advise whoever next occupies the Oval Office.
    As Obama begins reaching the milestones of a second-term president, like when he visited his 50th state last Friday, he's become more willing to discuss the next chapter of his life, making the outlines of his post-White House existence ever clearer.
    "I'll be done being President in a couple of years, and I'll still be a pretty young man," Obama told a crowd of students at a library in Washington last week. "And so I'll go back to doing the kinds of work that I was doing before, just trying to find ways to help people -- help young people get educations, and help people get jobs, and try to bring businesses into neighborhoods that don't have enough businesses. That's the kind of work that I really love to do."
    When he appeared on Letterman's show, Obama told the retiring host he and first lady Michelle Obama "want to continue to do the things we care about in a different capacity," which he said included helping military families and advocating for moves to stem climate change.
    In the past, Obama has suggested he might return to teaching, and he's widely expected to write a third book after his first two titles, "Dreams from My Father" and "The Audacity of Hope" earned him millions.
    Speaking to Letterman, Obama noted his oldest daughter Malia will have left for college by the time he departs office, though her younger sister Sasha will still be in high school. In the past, the Obamas have hinted they may remain in Washington until Sasha graduates from the Sidwell Friends School -- though they haven't committed to staying in D.C. past 2017.
    People close to the first family suggest a move to New York City could be in the works, rather than a move back to the red-brick Georgian home they still own in Chicago's Hyde Park. And while the White House regularly shoots down rumors that home sales from Palm Springs to Oahu are connected to the president, the Hawaii-born Obama is known to relish warm-weather getaways.
    White House officials insist‎ that for now, the President is mainly interested in governing during the "final quarter" of his presidency. Decisions already made during the first six years of his tenure -- bailing out automakers, signing Obamacare, killing Osama bin Laden -- already stand out as lasting elements of his legacy.
    In his second term, Obama has turned to executive action on controversial issues to advance his agenda items, including protecting millions of undocumented immigrants from deportation and enacting new regulations for power plants in a bid to address climate change.
    Two major elements to his foreign policy legacy have involved engaging nations once considered hostile to the United States. His meeting with Cuba's Raul Castro in early April marked a milestone in thawing relations between Washington and Havana, and negotiators continue working with Iran toward a deal to prevent Tehran from obtaining a nuclear weapon.
    Obama: Some communities have odds stacked against them
    nr sot obama brothers keeper_00001826

      JUST WATCHED

      Obama: Some communities have odds stacked against them

    MUST WATCH

    Obama: Some communities have odds stacked against them 02:00
    But even with those issues -- as well as fighting ISIS, brokering a new Asia trade deal and the rest of the daily duties that keep a President busy -- occupying the bulk of his time, Obama has been able to carve out time for his post-presidential plans. In that regard, he's no different than his most recent predecessors.
    In early 2007, supporters of President George W. Bush began raising funds for the Texan's eventual presidential library in Dallas, a center he also envisioned to include a conservative think tank.
    President Bill Clinton was similarly working to make plans -- and secure funds -- for his presidential library during in the two years before he left office.
    The White House has said the Obamas won't fundraise for their presidential foundation while in office -- though they've been active participants in the planning of their post-White House days.
    "Ever since Jimmy Carter, presidents have spent more time early on in their final two years preparing for what's next," said Julian Zelizer, a professor of history and public affairs at Princeton. "As presidents became more ambitious -- starting foundations and incentives -- they devoted more time to planning and fundraising for whatever they wanted to do."