[4][8] After university, Self moved to the Washington, D.C. suburbs, starting a job as a government IT consultant for now-defunct American Management Systems.
His shifted industries when he departed professional consulting and volunteered for the Howard Dean presidential campaign, starting in the fall of 2003.
"[9] It was on the ill-fated, but technologically progressive campaign that he crossed paths with Jascha Franklin-Hodge, Clay Johnson, and Joe Rospars.
As director, he oversaw the overhaul of critical platforms to help power the Democrats to regaining the majority in Congress during the United States elections of 2006.
His final year involved work in Australia[11] to help then-prime minister Kevin Rudd engage the public and use technology in political campaigns.