Barack Obama is expected to reflect on his achievements and regrets over eight years in office in his so-called "farewell speech".
"He's very optimistic about our future, but he believes. that our democracy is only as good as civic engagement and that if people get involved with their government, get involved in their communities, that the power of the citizen is the most important office of all", said Valerie Jarrett, a White House senior adviser close to Obama since his days as a lawmaker in IL.
For an example of how he might handle the speech, check out the remarks the president gave shortly after Trump won, or watch Michelle Obama's final speech as first lady.
Sheryl Harvey is shown with her ticket to President Barack Obama's final scheduled speech on Saturday, Jan. 7, 2017 in Chicago.
"It's not just where he raised his family, it's where he got his start as a community organizer", said White House Communications Director Jen Psaki.
The transition to Trump's presidency looms large over the address, and one senior administration official familiar with the speech-drafting process said that Obama recognizes the conflicting emotions within the nation's electorate.
Aides said the farewell address has been several months in the making.
Meanwhile, the architect of the president's two campaign victories and former top advisor, David Axelrod, said Monday he hopes the speech is more than a retrospective.
Bacos said that he would like the speech to arouse the same hope Obama promised when he first ran for president in 2008.
Obama's cross-country trek would be a sentimental trip down memory lane, were it not slap-bang in the middle of a tumultuous presidential handover. She said Obama will be encouraging "down the road" leaders to put themselves out there and seek office.
Psaki noted Obama's political career took off after he made a speech at the 2004 Democratic National Convention. But thanks to millions of Democrats like you, we've been able to prove them wrong time and again. Online sellers said they were offloading theirs because they were "struggling" college students or looking to finance a honeymoon.
Mr Obama was determined not to simply recite a history of the last eight years, and directed his team to craft an address that would feel "bigger than politics" and speak to all Americans - including those who voted for Mr Trump.
The event will live stream from the White House website and on the White House's Facebook page.
United States presidents have been giving farewell addresses to their constituents since George Washington.