[2] While at the Kennedy School, he worked with the Dudley Square Merchants Association to help them obtain a Main Street designation.
[4] After graduating from the Kennedy School, Yoon spent time working as a community organizer in Boston, providing housing for low income seniors and individuals coping with mental illnesses.
[5] Yoon also spent time working for Abt Associates, a public policy think tank, before becoming the Housing Director for the Asian Community Development Corporation.
[citation needed] In his first term, he was praised for his efforts to secure $5 million in funding for programs to prevent youth violence.
As a result of Yoon's efforts, hundreds of students rallied in the City Council Chambers during the 2006 budget hearing in support of the funding increases.
He also voted in favor of a salary increase for government employees, which he said would make positions more desirable for qualified candidates.
He requested the City Council minutes utilize "plain English" in order to make their contents more understandable to the general public.
He also called for the website to list as the names, duties, and length of term of the members of city commissions and boards.
[13] Yoon also proposed overhauling Boston's transportation infrastructure, advocating a plan that would increase bike accessibility and would promote rapid transit.
Yoon's strategy was to mobilize progressive voters in Boston who may have voted for Deval Patrick and Barack Obama, but who do not participate in municipal elections, which traditionally have low turnout.
Critics charged that this was a cheap political move by Flaherty designed to bring in minority and other voters that might not otherwise vote in the general election.